Do we really need more entrepreneurs?

Small businesses really are the backbone of the economy. Almost half of the US’s private sector workforce (49.2%) is employed by small business, and for the last twenty years, small businesses have been responsible for creating two out of every three (64%) of net new jobs.

Some of the most important innovations in the last century have come about because of scrappy entrepreneurs (Remember, Steve Jobs started Apple in his basement).

Small businesses also lead the way in innovation. A study conducted by the Small Business Administration found that small businesses produced 16 times more patents per employee compared to larger patenting firms.

We’ll always need doctors, lawyers and accountants, but we sure as hell need entrepreneurs, too.

Which is why we need to think about how we can pay it forward and help inspire, mentor, and empower girls and boys to think like entrepreneurs.

What inspired me to be an entrepreneur

When I was younger I never thought I wanted to own a business.

Some of my entrepreneurial friends had parents who owned businesses, but not me. My dad was a maintenance worker, my mother a nurse, and neither of them felt owning a business was a viable career move.

My parents knew that 8 out of 10 entrepreneurs who start businesses fail within the first 18 months, and that fail rate was enough to scare them into scaring me away from the thought of starting one.

But when I was 14 my friend was looking to pass off his newspaper route, the job that funded his much coveted video game and action figure collection.

I was too young to get a job at a fast food joint so wanting some financial independence for  video games of my own, I asked him if I could take it over.

For more than three years I would spend over an hour delivering newspapers after school every day of the week and early in the morning on weekends.

I didn’t realize it at the time, but my paper route job was grooming me for entrepreneurship:

• I had to be self-motivated to work; I didn’t have a boss calling me if I was late delivering. If I couldn’t do my route for some reason, like if I was sick or had a band practice after school, I had to hire one of my friends or my parents to cover it for me (and yes, my parents accepted the payment).
• It was up to me to collect payments from customers since the Mail Star would subtract their cut from my bank account automatically. I got to keep the profit. I needed to do some basic bookkeeping to make sure I wasn’t getting ripped off.
• I had to keep customers happy, deal with a bunch of different personality types, and sell subscriptions to new customers.
• I even cross-sold to customers, asking them if they needed their lawn cut during the summer months when they were away on vacation.

Newspaper routes are a great tool for teaching kids entrepreneurship. I cherish the experience, despite the click in my left shoulder I still have today from carrying the 100 pound bag uphill.

I may have ended up owning a business regardless, but this experience gave me a lot of the skills I needed later on.

The problem with school

Grade school highly discourages entrepreneurial thinking.

I don’t think it’s a coincidence that some of the most successful entrepreneurs were B students who later dropped out of college. As mentioned before, non-college graduate entrepreneurs include Mark Zuckerberg, Steve Jobs, Bill Gates, Richard Branson, Larry Ellison, just to name a handful.

The school system wants students to focus on the task assigned, not go off and dream up their own projects. Following direction is rewarded and deviating from it, coloring outside the lines so to speak, is met with punishment.

Guidance counsellors often encourage kids to pursue traditional careers, ones that require university education. There is very little talk of starting a business.

I am not saying education isn’t important, or that I’m representing every teacher in every school system in the world. Of course, math, English and science is important.  Of course, plenty of teachers inspire kids to follow their dreams.

Instead, what I’m saying is that the school system as a whole discourages entrepreneurial thinking on a fundamental level. They groom students to become good employees.

Entrepreneurial traits, like risk predilection and rebelliousness (a trait also common to teenagers coincidentally enough) are generally considered negatively and are suppressed rather than nurtured.

Successful entrepreneur and angel investor, Dan Martel went to jail and rehab as a teenager before starting his first business at 18 and turning his life around.

Dan has said many times that computers literally saved his life. Could it be that his mentors were able to harness his reckless energy rather than condemn it? That they nurtured his rebelliousness as a quality that could be used for good instead of telling him to fall in line?

I’m not going to pretend for a minute that I know more than professional educators. All I know is what I’ve experienced first hand and what other people have shared about what shaped them to be entrepreneurs when they were young and how they teach it to their own kids.

So how do we teach entrepreneurship to children?

In his awesome Ted Talk, Cameron Herald talks about the various businesses he made for himself as a kid, like selling coat hangers to dry cleaning businesses, and buying comic books from poor kids to sell at a profit to rich kids. It’s worth watching the entire video.

You may or not have children of your own, but even if you’re an uncle/aunt, or have friends with kids, you can play a role in their lives. You can inspire them to be an entrepreneur like you when they grow up.

Here are some key entrepreneurial traits Cameron mentions in his talk, and some ideas on how to nurture them in kids:

I also asked some friends of mine to share their stories with me, and tell me what shaped them to become entrepreneurs. I’ll share some of those stories here as well.

Problem solving

When you own a business, solving problems is a daily activity. Customers have problems. Employees have problems. Computers have problems. You can’t bury your head in the sand, you need to evaluate your options and choose a path to go down, even if it ends up being the wrong direction.

Kids are generally more impulsive than adults because they haven’t yet experienced the consequences of making bad choices.

Discipline expert Amy Morin recommends teaching children problem solving skills by:

• Identifying the problem and talking about it
• Come up with ideas for possible solutions
• List the possible benefits or consequences of each approach
• Be decisive and take action
• Allow them to experience any fallout or negative consequences of their decision (as long as they are safe)

“What helped me most is that I was always making my own money somehow, pretty much since I was 10. The message I received as a kid was: if you want something, you have to get busy and figure out how to do it for yourself. I never expected my parents to provide more than the basics, really. Learning self-reliance, trusting in your creativity, and developing courage is a great gift.”
Fiona Kirkpatrick Parsons, Marketing professional

The desire to make money

Once kids are old enough, teaching them to want money isn’t hard thanks to advertising. Kids learn how awesome money is at a pretty young age.

But there’s a big difference between wanting money and wanting to make money.

Making money involves work and kids appreciate money they’ve worked for more than money they were handed. 

When grandma gives a kid $20 for her birthday the first thing she wants to do is spend it. When she had to shovel the neighbor's driveway or knock on doors selling chocolate bars, suddenly that hard earned cash becomes more valuable.

“I grew up in the US around entrepreneurs, my grandparents owned their own businesses. My parents never said 'you can't' so I grew up believing I could do whatever I wanted. I remember working as a dishwasher at 15 years old making $3.35/hour, and then mowing lawns on the side at $20 per lawn, which would only take me 30 minutes. That's when the light bulb went off!”
Kevin Springer, Serial entrepreneur and co-founder, Proposify  

How to sell

I love how Cameron Herald teaches his kids to sell.

Instead of assigning them chores and giving them a set amount of allowance (which is teaching kids how to be employees), he encourages them to find jobs they think need doing, come to him and offer to do them, then negotiate a price.

But selling to your dad is one thing, selling to strangers is another.

That’s why door to door sales, like selling newspaper subscriptions or chocolate bars is a valuable training ground for future entrepreneurs. It’s teaching them how to speak to grownups, to get over the fear of rejection, and to use persuasion instead of nagging to get what they want.

“I sold candy in grade 6. I learned about working with a team, making a profit, and that you need your business needs to be defensible! The cafeteria ladies found out we were selling candy, and dipping into their profits, and had us shut down.”
David Howe, Serial entrepreneur

Customer service

Customer service goes hand in hand in sales. After all, once you’ve successfully convinced a prospect to do business with you, your job now becomes keeping that customer happy and fulfilling what you promised.

This is where jobs like cashier positions that teach customer service skills can help kids for later in life when they run their own business.

“I worked in a family run business from the time I was six until I moved out. I learned from pretty much day one that the money we used to buy food and to live on came from the drawer in the basement where we put it after we charged customers.”
Findlay Hilchie, Co-founder of Hustle & Grind

Tenacity

I’ve written before about how glad I am that I didn’t give up on building Proposify in the early days, and my experience is far from unique.

Entrepreneurs are going to struggle at some point, maybe for a long time, and some of the most successful business people did not make it because they were necessarily smarter than everyone else, but because they kept pushing ahead despite setbacks.

It’s hard because as a parent you never want to see your child upset, struggling, or frustrated but it’s important to teach children that nothing worthwhile comes easy, and not to quit just because they failed or it was difficult.

It’s better that kids learn to have grit at an early age instead of having everything handed to them, never needing to push through difficulties, and then discovering later as adults that the baby gloves are off.

“Going through two wars by adulthood, moving to Canada on my own at 19 with $1,500 in my pocket without really knowing anyone, and being homeless for the first week in Canada. All of it taught me to live day by day, and solve one problem at a time.”
Milan Vrekic, Co-founder of Zora Inc.

Creativity

Creativity is often most closely associated with art. But entrepreneurs are some of the most creative people out there. They are perhaps the only people who create their own job.

Entrepreneurs need to be observant and notice what people need (demand), find a solution (supply), sell that solution at a price people will pay, make a profit, deal with competition...and the list goes on.

How can you teach creativity as a skill?

Children should be given plenty of time for unstructured play, where they can use their imagination.

Cameron Herald has some nights where instead of reading his kids a story he asks them to make up their own story.

Some people think technology hampers creativity, but used correctly it can unleash it. Just look at games like Minecraft that encourage players to build whatever they want in a completely open, nearly infinite world. Smart phones and tablets let kids easily record their own videos.

Modern technology can be used along with more traditional activities, like learning an instrument or painting, to teach kids it’s OK to let your imagination run wild and pursue your ideas.

“In grade 12 I created a summer job with four other high school students. We applied for grants, mapped local recreation trails in our community, designed a booklet with environmental info, and paid ourselves. We learned a lot that summer!”
Michelle Doucette, photographer

Leadership

There’s more to being the boss than just bossing people around. You need to be a leader; inspiring, teaching, and motivating your employees to be the best they can be.

There are ways to teach kids to become leaders, not by encouraging them to be a bossypants (technical term), but by setting the example for them and being a good leader yourself.

You can encourage them to participate in team activities and observe how they interact with other kids. Don’t jump in if they have trouble or if another kid is being unfair. Let them work it out themselves.

“Being a swim coach and camp counselor taught me how to manage people and position them for success.”
Iaian Archibald, Co-founder of Swell Advantage

Networking

One of the most valuable things for me as an entrepreneur has been the network of friends, colleagues, and influencers I’ve acquired over the years.

Businesses are not created in a vacuum. Much like a child, it takes a village to raise a startup.

Having a wide group of people you know, locally and internationally, online and offline, provides a wide range of people to reach out to for advice, to pitch new ideas, to hire for positions, to make introductions.

Children can be encouraged from an early age to be interested in people. It starts with having them sit in on conversations between their parents and other adults, listen and ask questions.

If you’re part of a community group or church, encourage your son or daughter to be sociable, approaching and talking to older people in addition to kids their own age.

They may be naturally shy, but with practice even the most timid of children can come out of their shell and learn the value of making new connections.

“When I was a little girl, my mom had a eclectic group of friends who were entrepreneurial, and being around them made me want to do my own thing. I think as an entrepreneur you have a huge influence on the kids in your life, probably more than you would think.”
Krista Keough, Consultant, college entrepreneurship instructor

Conclusion

It may sound like a cliché but kids are our future, and if you’re an entrepreneur who either has children or influences someone else’s child, it’s important to think about how we can shape them into future leaders and job creators.

In other words, please think of the children!

In no way do I think I have all the answers. These are ideas to get the discussion started.

I want to ask you: What experience when you were a child/teenager shaped you to become an entrepreneur later on in life, and what are some ways we can teach kids to be more entrepreneurial?

If you’ve ever met me in person, you probably assume I’m an extrovert since I have a very loud laugh and can be outgoing in many situations. You might be surprised then to learn that the thought of attending a networking event gives me sweaty armpits (Sorry if that’s TMI).

I dread the idea of working a room where I don’t know anyone. Small talk over wilted carrot sticks and people plumping themselves and their accomplishments up….ugh.

Ummmm….Hi, my name is….

However, I do understand the deep value of in-person networking to help me excel at my job, to open career opportunities, and for personal fulfillment. Especially when I was freelancing, networking was crucial to developing new business.

Networking can also help you meet potential investors and mentors, and connect with people who can teach you about industry best practices and new trends or technologies.  

60% of people say that networking has helped them directly and indirectly find new clients, referrals, and job opportunities.

So in the same spirit of how I’ve learned to embrace sales and selling despite my initial discomfort, I’ve learned some tricks to minimize the agony of networking while maximizing the benefits.

Figure out what works for you

I am much more comfortable working a small setting like a luncheon or a workshop where people are seated at a table together than I am walking into a reception where everyone is standing around in clusters clutching their drinks and then have to figure out how to insert myself into those clusters.

If I’m at an event where we're at a table, it’s really easy for me to introduce myself, get the conversation going, and even connect others if they're feeling a little awkward themselves. I’m good at this and totally at ease with it, so I look for events in this format. Breakfasts, luncheons, dinners, workshops, and other small group events.

You don’t have to go to everything  - there’s no rule that says you have to go on every business boat cruise or cocktail mixer in your industry. Figure out which situations make you less sweaty and then find events to match that.

47.6% of people prefer smaller, more intimate networking groups compared to 4.8% who said they like large crowds.

Validate your events

In the same way you should validate your leads before spending too much time chasing them down for business, do the same for networking events. 

Not all networking events are going to have the kind of people you want to connect with. And the kind of people you want to connect with may change depending on your objectives. 

Going to an industry event to meet new peers and potential mentors might be great if you’re looking for professional development, but it’s not necessarily the right place to shop if you’re looking for new clients.

Or if you’re looking for investors, you need to find the events where you know people with money are going to be.  

Again, you don’t have to go to everything and it’s a waste of time and your energy to do so. Decide on your goal and find an event where the majority of the people attending that event can help you achieve it.

Research Attendees

Before I go to an event, I usually scan the attendee list (sometimes this is available on the event website) to see if there's anyone I’m interested in meeting. That way I can prepare a bit in advance what I might say as an opener, what they might be interested in, and the best way I can engage with them.

I also do a little extra research on what’s been happening in their business lately - maybe they won an award, landed a new contract, or started offering a new service. Anything I can find to connect with them on a level a little deeper than just, “So the coffee’s pretty crap, eh?” and demonstrate I’m interested.

Prepare your pitch

If talking to new people makes you tongue tied, having a script prepared in advance will help ease that worry.

I don’t mean reciting a speech or giving a hard core sell so you sound like a robot, but making sure you have good, natural responses to simple questions like, “What do you do?”, “What differentiates your business?”, What’s the opportunity?”, or “Why are you looking for investment?”

It may seem like a no-brainer but it’s surprising how blank your mind can go when you’re feeling uncomfortable.

Imagine questions you’re likely to be asked and then write down some general points of how you can answer them in a way that is accurate, interesting, natural, and leaves the door open to more conversation.

Also think about the different people you might be talking to, like a potential client versus an investor, and how you can tailor your answer to capture their specific interests.

Just don’t talk too much about yourself and your business. It’s important to ask questions, listen to the answer, and then respond with something that builds on the conversation.

It’s networking event hell to be stuck with a lukewarm wine glass in hand listening someone drone on about themselves. You’re here to learn about people and how you might mutually benefit each other and the only way you’ll do that is by asking questions and learning from the answers.

Act like a human

You’re going to be a red hot strike out if all you do is talk about business and hard sell everyone you meet. Like all social interactions, think about having conversations.

Those conversations don’t need to be only about business. Maybe they start with a concert you just attended, or you heard someone talking about their kid who plays soccer like your kid does, or it turns out you went to the same university.

People want to do business with people they can relate to, who they connect with. You’ll be more memorable that way when it’s time to follow up. So try to relax, take it down a notch, and act naturally.

Bring a buddy

Everyone needs a wingman, right? So when I’m cruising the event attendee list for potential people I might want to meet, I also look to see who might be going that I already know.

Knowing even one person at an event can give you a little comfort zone and an extra shot of confidence so you don’t feel like you’re the only loser in the room who doesn’t know everyone (guaranteed: there is no one in the room who knows everyone).

I also try to think of friends or coworkers who might benefit from the same event and invite them to come with me.

It doesn’t mean you only talk to that person but having a partner in crime can make it easier to break the ice, they might be more outgoing than you, and maybe they know other attendees to introduce you to. It’s kind of like water wings, you still have to get wet but at least you’re not going to drown, alone.

Some conferences and networking events have their own buddy programs to help first timers get the most out of the event. They’ll match you up with event alumni who show you the ropes and introduce you to other attendees.

This is great way to gradually warm yourself to an event where you know no one, rather than forcing you to immediately jump off the deep end as soon as you enter the room.

Manage your own expectations

Go easy on yourself. You don’t have to meet everyone in the room. Set a small goal for yourself, like talk with 4 new people, or meet that one potentially high value person that leads to a follow-up email or maybe even a meeting.

Keep in mind that networking is about planting seeds for longer term relationships. You don’t have to seal the deal right there over the stale pita bread and hummus. Make contact, make meaningful contact, and then nurture the relationship from there.

Pace yourself

If crowded social situations make you anxious, pace yourself. Further to the last point, don’t put crazy expectations on how many people you “should” meet or what the outcome “should” be.

Operate at the level that’s comfortable for you. That being said, I always think it’s healthy to push yourself slightly out of your comfort zone, otherwise how will we ever grow? So find the right balance and work it.

Take breaks between meeting people if you need to. Grab a drink, take a breather in the washroom, step outside as if you have to take a call and just catch your breath for a few minutes. Recharged, head back in and continue to work your business card swapping magic.

And don’t feel you have to stay for the entire event either. Decide to stay 30 minutes or an hour, whatever length helps you feel like you made a sincere effort without wigging out.

Volunteer

Like the “bring a buddy” tip, this is my other personal favourite hack to easier networking.

Events organizers are often looking for volunteers to do things like work the registration table or be a speaker liaison.

By volunteering, you’re instantly making a connection with the event and its attendees. You’ll automatically meet new people in a more natural way that gives you common ground, making it easier to start a conversation, and maybe you’ll gain access to those VIPs you wanted to meet.

I also think volunteering in general is a great way to expand your network, whether it’s for a charity, community, or industry organization. I wrote a post about How Volunteering Can Generate New Business a few months ago.

Follow up!

Don’t let all that prep, priming, and perseverance you put into actually attending the networking event and making connections go to waste. Follow up with the people you met, and soon.

Depending on how your conversation went, send an email or follow-up by phone within a few days of the event. Keep it short and focused, reminding them of your conversation, and then add whatever call to action might be appropriate. Maybe that’s a coffee date, sending a link to an article they’ll find interesting, a request for a full-fledged meeting, or maybe just touching base to say it was nice to meet them.

Keep your response in line with the last encounter in a way that moves the relationship forward naturally.

Network Your Existing Network

Sometimes it can be easy to overlook what’s right under our noses. Like the valuable network you already have with friends and former co-workers.

The benefit of this network is that you already know and are comfortable with these people so you don’t have to worry about how to break the ice. Staying up to date on what’s happening with them and filling them in on what’s up with you can help open doors and start new conversations that could pay off down the road.

Don’t get lazy though. Having sushi with your BFF every week like you always do is not networking. I’m talking about friends/acquaintances you don’t see or talk to on a regular basis, and staying in touch with people you used to work with - meet for coffee, lunch, or a beer after work.

I have found this enormously beneficial in terms of staying on top of what’s happening locally and gaining awesome intel on things like new jobs opportunities, potential hires, business leads, and good old fashioned industry gossip.

That person has sweaty armpits, too

Here’s a final thought to comfort you: 90% of people at a networking event either feel just like you do or has felt that way at some point. Everyone knows walking into a room of strangers can be daunting, even if you thrive on it.

But remember, everyone is there for the same reason: to meet new people, to make new connections. That’s the whole point of networking. They want to meet you, they want to hear what you have to say, and they have their own story to tell.

So slap on that name tag, grab a cup of watery coffee, smile, and fake it til you make it like the networking pro you were born to be.

After reading Remote: Office Not Required by the owners of Basecamp, or any number of blog articles on the subject like this one by Groove CEO, Alex Turnbull, you’d think it’s a open and shut case: remote working is the way the world is going because offices are stuffy, confining, and full of distractions.

I do admit that many of these articles make very solid points on why you should choose to go remote and how to make it work.

To sum it up, the reasons to go remote generally are:

• Access to talent - Not being limited to just your city means you have a bigger talent pool to hire from.
• Productivity increase - People waste time commuting, and people don’t get much work done due to constant distractions.
• Cost Savings - Office space, furniture, electricity, and internet are expensive.
• Happiness - People working from home spend more time with their family and can work when they’re most efficient.

My experience to-date

I’ve now had the experience of running two companies: one service, and one product, both of which have been remote at various points in time.

My first company, Headspace, started with four people remotely. After a couple of months we rented a cheap office. When our lease ran out we all started working from home before finally moving into a posh, trendy office a year later.

Once my co-founder and I exited Headspace to work on Proposify, we went back to remote, with three of us working from our homes and meeting once or twice a week at a coffee shop or pub. We eventually brought the team together again by renting office space from Volta, a co-working space for startups. Now, after a little over a year, we’re finally ready to move to our own office in about a week from this writing.

Throughout the last seven years while all of this back-and-forth between remote and office working was happening, I learned that when it comes to culture, collaboration, and communication, nothing beats having an office.

Regardless of whether you’re an agency or a product startup, those three things are absolutely crucial to the long term health of your company, not just optional nice-to-haves. Here’s why:

Culture

There’s no question that it’s easier to build a culture when people work together in a physical space.

Remote teams generally rely on communication tools like Slack to communicate. Some meet in person once a year. But in an office it’s different. Every single day you’re building one-on-one relationships with other people.

Random jokes are cracked in the office, and you can actually hear people laughing, which is so much better than just reading “lol” over chat.

Sometimes people end up grabbing lunch, dinner, or drinks together. At Headspace we also formed a basketball team and played in a rec league a couple of times a week, which was a total blast.

In the summer of 2015, some of us on the team went to Montreal for a few days for Startup Fest.

And during summer months, patios are a weekly occurrence:

Jennifer on our team has an actual bell in the office she rings when good things happen, like when a big customer signs up, we hit a financial milestone, or a hilarious joke is made.

Oh and Slack? Yeah we do that too, even when most of us are in the office:

The point: If you’re looking to build a strong culture where people work hard and play hard, and where friendships are forged, it’s going to be very difficult to do that with people who are in different time zones only communicating through a computer screen.

Communication & Collaboration

Sure, there are lots of great chat and video conferencing tools like hangouts, Skype, UberConference, etc., that make communication and collaboration easier.

But how many times have you been trying to have a video chat with someone when something goes wrong — internet connection cuts out for a second or there’s a delay or echo, or some other technical wonkiness — that makes it hard to keep a rhythm to your conversation and kills the energy of your meeting?

When meeting in person you can sketch on a whiteboard without anything hampering your ability to see and hear what the other person is communicating.

And when teams work together in a space, special things happen.

Just a month ago, my CTO and I were casually chatting when we started coming up with big ideas for how to improve our product. So we jumped into a meeting room and had one of our most creative brainstorming sessions ever and solved some big conceptual problems.

The meeting was never planned and it wouldn’t have happened if we were in hammering on our keyboards in different time zones.

I believe that in a digital agency environment this kind of in-person communication is absolutely essential to creating the best work for your clients. You just can’t brainstorm concepts effectively over Skype.

Plus, when working remotely, it’s too easy for people to plow ahead in the wrong direction, and they tend to work in silos.

In a product company you may not need as many meetings, but especially when you’re using an agile methodology like we do, two week sprints require a lot of short, focused meetings to make sure everyone is on the same page and knows what they’re doing.

How to overcome challenges of the office environment

This isn’t to say office culture doesn’t have its downsides. Here are common reasons people give for why office culture doesn’t work, and how we get around them here at Proposify:

Productivity

You might wonder how, with all of this zaniness going on at Proposify, we get any actual work done.

Admittedly, we have to keep a close eye on distractions to make sure we aren’t pulling people away from important work they’re doing.

Right now we’re all working in one big room together, which isn’t ideal. That’s why we’re moving to a space that’s broken up into multiple rooms, to avoid the problems that come with open concept offices.

Currently if there’s a lot of talking and laughing going on and someone is head down in something, they are welcome to grab their laptop and move into a quiet meeting room to finish up (or ask everyone politely to be quiet).

If people are collaborating on a project together or talking to a customer on the phone, they’ll respectfully leave the main room to talk so they won’t distract others.

Coding, designing, or writing content requires hours of focused concentration, so on occasion our people can work from home for half a day, or leave and go to a quiet room to work where they won’t be bothered.

In our new office we’re planning to designate one room as the quiet room, where talking is illegal and people can go there to code or write without any distractions. We’ll have to work out some kind of a medieval punishment for infractions.

And of course when there is unforeseen downtime, or during regular weekend releases, people work from home and communicate via Slack.

Access to talent

Honestly, I’ve never really understood this one.

The Proposify team lives in Halifax, Nova Scotia in Canada. We’re pretty far east and tucked out of the way, and Halifax is a very small city (just over 400K people).

Yet we’ve been able to find incredible talent; designers, developers, marketers, customer support, you name it.

I have a hard time believing that people in bigger markets like Toronto, Montreal, and New York would have a smaller talent pool locally to choose from.

We work hard to build a great culture and attract talent, so it hasn’t been too hard to find talented people right here.

Worker happiness

Working from home is often considered “the dream”, but is it really?

After the initial novelty wears off, it can become its own magnet for distraction. There’s laundry and cleaning to do. Kids need rides somewhere. Dogs need walking. Spouses or partners pop into your office to talk about last night's Walking Dead.

You need a good setup to work from home effectively. For people with pets, partners, and kids, it can be nice to see them during the day, but they can be more distracting than a teammate. At least teammates have their own deadlines to meet.

Also, you can get serious cabin fever by never leaving your home, and it’s easy to forget about showering or getting dressed. After a while there becomes no separation between work and home, and people can find themselves working even longer hours than if they were in an office.

Some people counter this problem by working at coffee shops, but that makes it hard to have private video chats, and there’s still a lot of distracting conversations going on around you, it’s just coming from strangers and not your teammates.

The fact is, you can build a lot of flexibility into an office culture by letting people work their own hours. We have one developer who comes in around 7:30 AM  and leaves at 4 PM. Or let them work remotely sometimes, like days when they have personal appointments.

Expenses

Office space is expensive, especially if you want to be located downtown where it’s central and relatively easy for people to commute.

You don’t need to rent office space right away, but as you begin growing your team beyond three or four people, you’ll need to start looking at a cheap alternative, like a shared co-working space that can hold you over until you can afford your own space.

Let’s face it, salaries are a lot more expensive than rent, so if you can afford to hire a team of people, rent isn’t that much of an expense by comparison.

Proponents of remote teams who complain about rent costs often fly their team to a central location every year and pay for their food and hotel rooms. That one event alone is likely the cost of a year’s rent.

Conclusion

Just because you have an office doesn’t mean it needs to be a grey, fluorescent- lit, cubicle-filled dystopia where dreams are crushed.

It also doesn’t need to be a pretentious, open-concept beehive where people are inundated with distractions and purposeless meetings.

Done right, creating an office base can offer everyone on your team a fun culture, better work-life balance, and effective collaboration that makes the work more rewarding.

I respect other founders who can make remote teams work. But after living both sides we made the decision early on that building a world-class company right here in Halifax, Nova Scotia is the way to go. So far it’s working for us.

I’d love to hear what you think in the comments below.

Hubspot CRM Integration

You asked, we delivered! As of Saturday, April 9th, 11 AM EST, you'll be able to connect your HubSpot CRM to Proposify so you can stay up to date with your proposal progress right in HubSpot.

Simply enter your Hub ID into Proposify, accept the connection and you're ready to go.

Once connected you can select where in your pipeline you want proposals to be moved as the sales process moves forward. You can also import all your contacts.

When you create a new proposal it will automatically be added to HubSpot CRMwith all the details. Once you send it and ultimately win the proposal, HubSpot CRM is updated each step of the way.

You'll find a link to the proposal in HubSpot and a link to HubSpot from Proposify in the proposal settings.

We hope this integration will further streamline your sales process and let you focus on winning ;)

List Updates

We've also been working on improving lists: how they behave in the editor, pasting into lists, and general list editing. Hopefully these changes put Proposify on your good list (see what I did there?)

Thanks,
Ricky Ferris
Proposify Product Manager

In the space of the last 8 years I’ve gone from full time to freelance to full time again.

When I was a fulltimer I never thought I’d be interested in going freelance.

Then I went freelance for six years and I swore I would never go back to a regular job again.

Now here I am with almost a year under my belt working full time for Proposify.

Obvious lesson? Never say never, my friends.

I’m here to prove that you can survive this teleportation and I’ll share what I’ve learned in the process.

Full Time Freelancing

Before we get too far I want to address the word, ‘full time’ being used as the opposite to ‘freelance’. It’s what most people say to mean they work full time in an office, or in-house.

This maybe suggests that as a freelancer I wasn’t working full time, or rather, not hard enough. Sure, my hours were probably different than someone going to an office every day, but I was still working a lot, and hard. I was a full time freelancer.

But because it’s the vernacular, for the purposes of this article I’ll use the term ‘full time’ interchangeably with ‘in-house’ to mean you work in an office for someone else, as opposed to freelancing.

Just know that I know that all you freelancers out there are working hard for your money.

Freelance to Full Time is not Failure

Sometimes when I was working as a freelancer I thought people might think I had gone out on my own because no one would hire me for a full time job.

Of course that wasn’t true. I had worked many years for other people but I wanted to try things on my own terms and the timing was right with some immediate opportunities for freelance projects. 

The same feeling started to plague me when I considered working full time again. Everyone knew I loved working for myself so after six years if I was really that successful as a freelancer, why on earth would I give that up to work for someone else — unless I had failed?

It really bothered me that people might think I had failed.

But that was just negative self-talk I needed to get over.

My reasons for deciding to go back and work for someone else were varied, the same as my reasons for going freelance in the first place. And none of them involved failure.

The reality is, as much as I loved freelancing, there are a lot of challenges working for yourself.

The Joy of Payday

Regardless of the fact I worked steadily, cash flow was always a bitch.

While I had a couple of regular gigs I could count on, it was hard to know how much work I would have long term, and more worrisome, when I would get paid.

Also, some agencies wouldn’t pay me until their project finished and they got paid so it could be months after I did the work before I would finally see a cheque. If only Kyle had written his post about collecting on invoices years earlier!

I’m not going to pretend that the best part of working full time isn’t the biweekly, dependable paycheque.

It is.

There are a number of other things I like but all things being equal, getting paid regularly without having to chase down clients is pretty damn great.

It’s right up there with PAID VACATION.

Career Advancement

When you work in an office for a company, you can usually see the path you want to follow to move your career forward.

For example, you’re a designer so maybe you work your way up to becoming an art director and then eventually creative director.

But when you work for yourself it can be more difficult to see how you advance your career and skills. Who’s going to give you a promotion? You can crown yourself queen but that doesn't mean you’re royalty.

It’s one of the major reasons I decided to join Proposify. I’d been working in the marketing agency context for almost 15 years. I loved it and I got to work on lots of different projects for different companies but even when I was freelancing I was basically doing the same type of work, offering the same services, producing the same types of deliverables.

So when Proposify’s co-founders Kyle and Kevin — who also happen to be my friends and former co-workers — approached me about joining their team, I was intrigued. 

Here was a chance to work with a startup (something I had never done), to help grow a new business (it was less than 2 years old when I joined), to apply my knowledge and experience to a totally different industry (what did I know about SaaS?), to focus my attention on one brand (rather than five), and to help my friends put the pedal to metal in building their company.

I was happy freelancing and doing the work I was doing but with this offer from Proposify I could see the next step in my career and I could see the potential for how it could help me grow both professionally and personally.

Co-workers

For much of my career I’ve worked with some really great people. I met the bulk of my closest friends through work. That’s part of the reason why I was originally hesitant about going freelance, I liked working with a team. I liked being around people (well, most of them).

Fortunately for me, I was still part of a lot of teams at agencies where my friends worked and I would often gang up with other freelancing friends to work on projects. I generally got to choose who I worked with.

I felt like I had the best of both worlds when I was freelancing  - I worked with people just enough to satisfy the social beast in me and then I could escape all the crazy that can happen like office politics and petty infighting.

When people would ask me if I ever considered going in-house again I would say that I preferred playing the field to getting married.

When I started at Proposify I was looking forward to being part of a full time team again but the reality has been more challenging.

I like everyone I work with but I wasn’t used to being around people all day, every day. I’ve also had to relearn aspects of office culture and working with people with different experiences and backgrounds.

I had spent the last number of years working with people who were very similar to me doing similar work. We were of like minds, similar sensibilities, and similar skills.

Basically I ended up isolating myself, not necessarily in terms of quantity of social interaction but the type of social interaction. So it’s been good to shake things up a bit and break out of my self-imposed bubble.

Pace Yourself

People often hire freelancers because they’re in a time crunch to get things done, whereas working in-house you typically have more time to properly flesh out ideas.

I also would get hired for pieces of projects, so smaller chunks of work to be completed in a shorter timeframe. I was used to kicking out projects quickly, in sprints. Execute, execute, bam, bam. Get it done, make the revisions, on to the next.

So when I started at Proposify I felt like I had to accomplish the role of marketing manager in two weeks.

It was an absurd expectation and one only I was responsible in creating. But I was so used to working on a project-to-project basis with a crazy deadline looming over me that I felt a level of anxiety in the first month working on my job. I WASN’T DOING ENOUGH FAST ENOUGH!

Fortunately I came to my senses and reminded myself that this was a marathon, not a sprint. Yes, there were things to get done and there were deadlines attached but I didn’t need to have everything figured out and executed in the first two weeks.

That’s the beauty of working for one brand instead of twenty. You can think, strategize, execute, test, and try again.

I’m privy to the big picture and able to contemplate what the next steps are, rather than being asked to solve one section of a puzzle I’ve never seen.

Flexibility

This is probably one the biggest benefits most freelancers will list about their jobs. That they can decide when and how they’re going to work.

If I had other things I needed to do I might work for the morning, take a couple of hours in the afternoon to run errands, and then work all evening.

Or if I hit a wall one day and just couldn’t get ideas or words to come, instead of sitting at my desk in agony trying to force my brain to work, I could take a walk, go kayaking, then come back refreshed and ready to rock. Even if I was working under a tight deadline, as long as I met the deadline, how I got there was up to me.

I could decide what kind of projects I wanted to take. I had a rule about working with assholes. I could fire a client or sometimes if the deadline or budget expectations of a project were totally unrealistic, I would just say no. I was never able to do that when I worked for someone else.

Don’t get the idea I was turning down work like some sort of entitled prima donna. But there was a reason I worked for myself and personal happiness was a major part of it. It provided huge peace of mind to know that if I wanted to, if something or someone was really causing me that much stress, I had the power to say no.

Going back to work full time has changed that. Although Proposify is pretty flexible, I don’t have quite the same freedom with my time and I have a more structured work day. But I’ve actually liked that change for the most part.

Working for yourself, you can end up working all the time. There’s always something to do plus when you’re not sure when or if the next job is going to come along, you feel like you have to say yes to every project.

You end up not taking the breaks you need or creating work/life boundaries that are essential to your mental health and personal relationships.

While I often do work-related reading or work on my blog posts in the evenings because it’s quiet, I now am able to keep most of my work happening during the day. I didn’t realize it was that big a deal until my boyfriend mentioned it recently - that it’s been nice that I’m not working all the time.

Move Carefully, Choose Carefully

Overall, while my transition from freelance to full time has been an adjustment, it’s been a positive change for me.

Part of the reason is that I was open to the change, and I was fortunate that an opportunity like Proposify was my re-entry point to the full time world. I chose it deliberately for very specific reasons:  

I’ve known Kevin and Kyle for many years. I know that we share similar values when it comes to work/life balance, to respecting people, to valuing good work and a good laugh at the same time. And they know me  - my experience, how I can contribute to the company, and they trust that I’m going to do my best.

You should keep these things in mind when choosing any job but especially when you’re going from working for yourself to working for someone else.

While there will always be challenges to any change, being on the same page will increase the chances of a successful full time teleportation.

Conclusion

I’m not suggesting that full time is better than freelance or vice versa. They both have their pros and cons depending on your work style, your tolerance for risk, self-discipline, and social skills. It also depends on timing and opportunity.

But having punched from both corners of the ring, my advice is to be open to the idea of change — either jumping into freelance or returning to full time — and recognize that change brings growth.

For me, that change led me to Proposify.

In the past, I usually hired friends I had already worked with many times before, or I bought a single job ad on Career Beacon. Hiring was messy, but I got the job done.

It generally involved me sifting through 100 emails, putting them in a folder in Mac Mail and flagging the appropriate candidate. There was no process when it came to recruiting, interviewing or onboarding, I just went with the flow.

This time was different. We needed to hire for five new roles and I wanted to streamline the process so that it was more collaborative, organized, and reduced any duplication of effort.

Writing the job ads

Writing a job ad is pretty much the same as writing any other kind of ad — you’re trying to attract your target audience and get them to take action.

As obvious as that sounds, I often see other company’s job postings that read like they were written by robots, for robots.

We wanted our job postings to be a reflection of our company’s brand. We are people with personality, and we want that to come across in everything we do.
So Jen and I wrote a standard intro for each job posting that outlined why a talented employee should even want to work at our company.

Then, after outlining the job requirements, we listed the benefits at the end of the post.

Adding “a good laugh”, “Friday happy hour” and “a good joke” in the job posting has helped us find people who also appreciate fun, which is an important factor in a team. We want people laughing every day. Fun makes it easier to get out of bed every morning and come to an office.

Finally, at the end of the requirements listing, we wrote the following: “Please forward your resume along with a thoughtful cover letter.”

This was done specifically to filter out candidates who shotgun blast their resume to every job posting they could find. The people who didn’t write a cover letter, or their cover letter was generic (“Dear sir or madam”) were instantly rejected.

We want thoughtful people who care about the details, and so this is a good way to know right away who isn’t that.

By the way, we wrote job postings for a designer, full stack developer, salesperson, customer support person, growth marketer and QA analyst. 

Click here to see all the postings. Feel free to copy the text to use in your next job posting.

Managing the process through Qimple

I used to use my email program to organize job applicants. Then I heard about another eastern Canadian startup called Qimple, which was a game changer. Qimple made our whole hiring process much more streamlined.

Here’s how:

First, it guides you through the creation of your job posting, outlining the different fields, categories, responsibilities, and skills/qualifications you want to include:

Once you publish your job posting, Qimple creates a branded page you can share with your social networks and that applicants can apply through.

When someone clicks the “Apply Now” button it walks the applicant through the process and lets them import their LinkedIn profile, upload their resume, or create their own Qimple account.

Promoting your job posting

Qimple makes it easy to promote your job through virtually every job board, including Workopolis, Indeed, Career Beacon, Monster, and Stack Overflow plus they offer you discounted postings!

Once you add a particular job board to your cart and check out, Qimple automatically posts the job ad to the third party website without you needing to do anything.

I loved the fact that I could choose on a per job basis which job board I wanted to advertise through. For example, promoting just the developer job through Stack Overflow, or just the design job through Dribble.

Reviewing applicants

Qimple also makes reviewing applicants more organized.

You can click on a job to see all the applicants for that position, filter/search them, and thumbs-down the ones you know you won’t contact, or thumbs-up the ones you think stand out.

When you click on an applicant you can see their experience, cover letter, and resume at a glance.

You can contact the applicant through Qimple and they offer pre-written email templates for things like setting up interviews and rejections.

And instead of getting emailed every time there’s a new applicant, I chose daily notifications so every day I got a summary of who applied and for which position.

Finally, I invited my team into Qimple so that when I spotted a promising applicant I could simply Slack the appropriate person a link instead of forwarding emails.

In case this hasn’t been clear, I’d highly recommend starting a trial with Qimple for your next job posting!

Qualification questions

So we’ve got a steady stream of applicants flowing into Qimple, and a process for vetting and reviewing them. Now what?

Here’s what I looked for in each candidate:

• A strong cover letter that made it clear the person researched our company and understands who we are.
• The skills we’re looking for.
• A decent amount of relevant experience depending on the position.
• Personality.

Once someone made the short list, our next step was to qualify them with a set of email questions and whether or not they got a call from us depended on how they answered.

The questions varied a bit depending on the position, so I’ll outline what we did with each specific job:

Customer Support

When hiring a customer support agent, you need to know how they communicate and solve problems.

Here are the questions we sent to candidates:

1. Imagine a potential customer emails you with the following question: “I’m considering a switch to Proposify, but I was wondering if your software lets me add forms to proposals?” Proposify doesn’t offer this feature yet, but their current proposal app does. How would you respond?

2. Imagine that you’re just starting your workday, and you login to our help desk to see 30+ emails from distraught customers who can’t access their accounts. Clearly, something big (e.g., a server outage) is happening. What steps do you take?

3. We’d like to get an idea of how you can clearly explain concepts and processes to customers. Tell us step-by-step about something that you shop for online, and how you go about searching, choosing, and purchasing it.

BTW, I stole these questions almost verbatim from the Groove blog. Thanks, guys.

Developer

When a good developer candidate pops up, I usually take the following steps:

I call them on the phone first. I do this because often developer’s cover letters/resumes are fairly dry, so I want to get a sense of their personality right away.

How do they react when I call them up?

Are they friendly, courteous, and able to adapt to the conversation without any preparation?

There’s no point hiring a developer with great coding skills who can’t communicate or hold a conversation.

I ask them what they’re currently working on, how they feel about it, and about any particular technology they’re working with. I let them know about our stack and ask them if they have experience with it. Overall I’m trying to get a sense for how they talk about work and technology.

Finally, I ask them why they applied to our company. I want to know if they actually are interested in what we’re doing or if they’re just looking for any job that pays.

After the phone call I follow up with an email to ask for code samples. Jonathan, our CTO, wants to see something they wrote. Many developers have side projects and host their code on Github. Jonathan wants to check out their style of coding and any interesting things they’ve built.

Designer

The nice thing about design is that the proof is mostly right there on the page. A designer’s portfolio shows exactly what their output looks like. Of course, it’s also important for the applicant to describe the process behind their work and how they arrived at a solution. So in this case, no pre-qualification questions are needed before inviting them to an interview.

Quality Assurance

With a QA tester, we want to know their process for testing, identifying, and communicating errors, so we ask them:

1. Imagine a support rep shows you an email from a customer that says “Help! Your product is full of bugs. I can’t get bullets to flow onto a new page and when I try to change the formatting nothing works.” Describe in detail the steps you would take to find and trap the bug, and how you would communicate it to the development team and customer support rep.

2. Sign up for a free trial of Proposify and find at least one bug, then describe how you found it, what you expected would happen, what happened instead, how to reproduce it and any additional detail that may help the development team fix it (i.e.: browser, console errors, broken markup, traceroutes, etc.)

Growth Marketer

When hiring a growth marketer, who you want to be 100% dedicated to driving growth for you or your clients, they need to be analytical and take a scientific approach to running growth tests.

When hiring for this position, we knew we didn’t want an inbound/content marketer, and we definitely didn’t want a communications or PR style of marketer.

So we asked these questions:

Talk about a growth experiment you applied in the past (successful or otherwise).

• What was your hypothesis?
• What process/system did you use to prioritize running this test?
• How did you measure the impact of the test?
• What convinced you that the test yielded enough statistical significance to end the test?

Managing the interview

If the candidate passes their qualification email, we have them in for an interview. I’ll generally invite a manager or team member from that department in on the interview. They’re going to be working with the new hire, so they need to feel as comfortable as I do.

I believe that interviews should be informal and conversational with no need for check lists or predefined questions.

We already know their skills based on their resume, samples, and/or interview answers. At this point, we’re looking for fit, and I can’t get an accurate feel for that if I’m lobbing goofy, pre-canned questions at the person while they nervously try to say the right thing.

I’ve conducted interviews before where we walked down to the food court to grab a coffee. I’ve gone out for a smoke with a candidate (I know, I know; smoking is bad and I will quit). Anything that puts them at ease and makes them feel like we’re just two people talking.

There are no standard questions I ask. I don’t ask them what their weakness is, or anything like that.

I ask about their current job, where they’re from, what they’re interested in, what they’re passionate about, how they got to where they are, or to talk about something they’re proud of that they did in the past.

I let them know how our company came about, my background, and give an overview of the team structure. I need to feel like they’re intrigued by what we’re doing and that they want to work for a startup.

There’s one thing we add when it comes to interviewing developers. We actually make applicants take a test when they arrive on the interview.

That may fly in the face of everything I just said, but the reason we do it is because we’re often looking for developers who write pure, object-oriented Javascript, and some developers only know basic JQuery.

We ask them to take a 15-question, written test to prove that they know the language on a low-level. We don’t sit in front of them while they do it, and we give them as much time as they need. Also, we don’t require a 100% passing grade.

By the end of the interview, we should know whether or not we want to hire the person. If we do, I’ll ask about salary expectations, start date, and tell them we’ll call their references.

References

I’ve made hiring mistakes in the past where I got so excited about the candidate that I hired them on the interview without checking references. Not surprisingly, I got burned.

I always call at least one reference before making a decision, with preference given to past employers rather than past workmates.

Like the interview, I am informal when it comes to calling references.

In a conversational way, I want to find out:

• When they worked with the candidate
• What the candidates strengths are
• If there were any problems in the past I should know about

Yes, I’ve actually had a reference tell me, “Bob is a great developer, but it’s hard to get him to focus on a task and he often goes off and builds something awesome, but not what you need.”

That right there was the end of the road for that applicant.

Calling references may seem old-school and unnecessary, but it’s an important final step.

Making the offer

I have a simple job offer Google Docs template that I customize for each new hire.

Click here to view the template

I import the document into DocuSign and send it off to the candidate for sign-off.

After the candidate signs the offer, I send out a standardized email with the following information:

• Welcome to the team
• Confirm where to be on the start date and what time
• Introduce them to Kevin, my co-founder, as the point of contact for payroll, benefits and stock options-related questions
• Introduce them to their manager or the person in their department they’ll be working directly with. (This person was already involved in hiring them)
• Offer to answer any other questions they have (like dress-code, which some people still hilariously ask about)

First day onboarding

You may have found the perfect person but your work isn’t done yet! To complete the hiring process you want to make sure your new employee is properly onboarded. The last thing you want is to seem disorganized and leave them twiddling their thumbs on their first day.

Preparation

A week before the start date, make sure you have their laptop and any other equipment ready to go, and have a list of all the apps they need installed.

Kevin follows up on the information needed to get them on the payroll and benefits plan.

I create a temporary password for all their accounts (mail, Mac account, Slack, Trello, or whatever SaaS tools you use) and leave it on a sticky note so they can easily log into everything.

First day agenda

We began a tradition where new employees sit privately one-on-one with the co-founders (Kevin and me) when they first arrive.

I found it helpful to put together a slide presentation to review who we are, our history, our target personas, the key benefits of our product, and our processes.

After this initial meeting, we’ll go over the product in more detail, run through the various apps and tools we use, and then introduce them to the person in their department who will be their go-to for questions.

Later that day or in the first week, Kevin and I also try to make time to take the new person out for lunch and get to know them on a more personal basis, their interests and hobbies.

Conclusion

This process has greatly simplified hiring new employees, saving time, getting appropriate input from team members, and finding (and hopefully retaining) the best talent.

I found with this round of hiring that the process was a lot more seamless, but I still feel 100% confident about every new person on our team.

What’s been your experience hiring? And good tips or nightmare stories to share?

I’ve written before about how growing up I never really imagined I’d end up working in business. But with a 15+ year career in marketing/communications which includes owning a small side hustle for the past five years, running a freelance practice for six years, and now working here at Proposify, it’s a good thing I didn’t have my heart set on a career in fortune telling.

Even though I was thinking about being a writer, teacher, journalist, or spy, it turns out that I was learning a lot of lessons about work and entrepreneurship from my parents that have benefitted and shaped my career.

For most of my life up until I graduated from university, my mother was single and working. She was a secretary from the mid-70’s to the early 90’s for law firms, an eye doctor, and a university. (And I use the term “secretary” on purpose because that’s what it was called then.)

My mum worked hard, was smart and capable, got paid crappy, and had to deal with the kind of sexism that may seem like a cliché to us now but was common during that time toward a young, single, divorced woman in an office.

My father was a tireless, serial entrepreneur. In fact at 71, he’s still working it as VP of sales for an educational software company. While he started his career in social work, he decided early on he wanted a change, to work for himself.

So in the mid-70’s he moved to a rural area renowned for its terrible economy and started the very first recycling operation in the region. Over the the next 30+ years came other businesses and ideas for new ventures.

In the early 80’s he started selling Texas Instruments personal computers at a time when NO ONE had a computer in their homes. Then a few years later he became the first Apple dealer in his region, and this was way before Apple was the cool kid on the block it is today.

He also developed software to help doctors manage their billings and created a history program for elementary schools.

My parents have very different personalities, careers, and lifestyles and naturally I learned a great deal from them about life, as children do. But I’ve also learned some very specific things from both their career experiences in terms of how I approach work, business, and entrepreneurship.

My brother and me going off to work at our first jobs at my dad’s recycling company.

Iron Your Hoodie

This may sound like a silly business lesson but both my parents always look good. Not glamorous, not flashy, not expensive but they always looked pulled together and appropriate.

My mother said that there were tricks to make you stand out (or blend in, as the case may be) even if maybe you didn’t have the same money or background as the next person. Looking clean, polished, and professional was one of those ways. Good manners is one of the others.

I’d see her going out the door in the mornings - hair and makeup done, a smart, professional dress (bought on sale, of course), hose, and stilettos (oh, the 70’s). The way Mum dressed she likely looked ‘above’ her position but it gave her the confidence to command respect and professionalism at her job.

Even when my dad’s in his home office and likely isn’t going to see a client, he always puts on a nice sweater/shirt combination.

As a result, I’ve learned how to use my clothes to help set a tone for meetings and my own attitude. Depending on the client, on the situation, on the relationship I want to establish, I dress for that part. Job interviews, new clients, new co-workers, new partners, the bank.

I know office life is much more casual now, especially in the startup world, and I’m not suggesting I wear a suit every day but I am conscious of how what I wear and how I wear it can both affect how I feel about myself and how others see me.

In a business situation, those are important things to manage.

Give Them More Than They Asked For

Both my parents are really big on exceeding people’s expectations. In school Mum used to tell me, “If the teacher asks you to write 500 words, give them 750. If you’re told to show up at 8, show up at 7:45.”

Sometimes I would argue back that there was a reason a teacher would ask for only 500 words and you would get penalized for going over but I got Mum’s point.

The same with my dad. Just the other day we were talking about how he likes to get back to his clients before he said he would and provide them with a little bit more information or a little something extra than what they were expecting.

I remember when he sold personal computers in the 80’s there were lots of times he would drive over to a customer’s house in the evening to provide support (IMAGINE!).

It’s part of the reason why through all his businesses he’s had really great relationships with his customers and partners. They always appreciated the extra, it made customers feel looked after, and special. That Dad was taking care of business, their business.

This “extra” approach wasn’t lost on me. I’ve tried to apply it through my whole career - being extra prepared for meetings, doing background research, providing more detail in emails or briefings than was asked for, being flexible with clients.

I know that in business you sometimes have to monetize the extra or you can end up in costly situations like the dreaded scope creep but there are still ways to add extra value that doesn’t involve a lot of money.

Shockingly, sometimes just doing what you say you were going to do is perceived as extra by clients.

Don’t Take Shit

As I mentioned earlier, my mother worked as a secretary at a time when there was no such thing as a sexual harassment policy and there was little awareness if any about the inappropriateness of sexist comments and behaviour.

But being a young, divorced woman in a support role for professional men, she, like many of her co-workers, regularly experienced in real life the kind of fictionalized situations we watched on Mad Men. Sometimes subtle, often blatant, but it was there.

My mother has a strong personality and a good sense of herself so sometimes she was able to push back but because of the times, because she needed the job, there were other situations when she just had to let it roll.

This had a profound effect on me growing up and when I started working I vowed that I would speak up and speak out, whether I experienced sexism or rudeness or general disrespect happening to me, or to someone else.

Sometimes there’s been a situation that doesn’t really bother me but then I think about it happening to someone else who might not feel they have the power to speak up if the same thing happened to them. So I feel compelled to speak up on their invisible behalf.

Knowing I have the power to push back has given me confidence in business situations when someone has tried to make me feel small, to minimize my contribution, or to exert control over a situation they have no business controlling.

It has made me almost fearless. Not just in terms of fighting jerks in the workplace, but about almost everything. And feeling fearless is a really valuable and empowering trait when it comes to being an entrepreneur, owning your own business, or just trying to get move your career forward.

Be Nice

I know there’s this whole negative thing about nice, especially when it comes to business and I just don’t get it.

People have mixed up being nice for letting people walk all over you. They’re not the same thing at all.

My dad is one of the nicest people you’ll ever meet. He’s charming and funny and personable and polite and, well, nice. He treats everyone he meets with respect and he errs on the side of “we’re going to be friends” as opposed to viewing people as adversaries right off the bat.

His niceness set him apart in business. It’s what his customers remember about him. It’s why they continued to do business with him over the years. It’s how he’s built great relationships with industry colleagues and business partners.

At the same time, my dad’s no push over. He is sincerely a nice person but he has a line, that line may be farther away than most people’s, but he has it. And he won’t let you cross it, he won’t let people take advantage of him, he won’t let them be rude, he won’t let them be disrespectful.

If he thinks you’re not on the right track or you’ve done something wrong, he’ll tell you. But he’s no ‘tough son of bitch’ that many people think is the persona you have to adopt to be successful in business.

I’ve always admired this about him and I’ve watched how it has worked to his benefit in both his personal and professional life.

I seriously believe in the wise words of Mary Poppins when she said, “A spoonful of sugar helps the medicine go down” and I would put it on my “Top 10 Quotes That Have Inspired Me in Business”, if I were to ever write such a thing.

I don’t buy the business bully attitude of the Shark Tank’s Kevin O’Leary or the idea of being a “boss bitch”.

I believe you can be successful in business, be fearless in your attitude, get shit done, and still be a nice person.

Nobody Owes You Anything

Both my parents worked incredibly hard under difficult conditions to thrive, to provide for their family, and to achieve their own personal goals.

But I never, ever heard them blame someone else about the situation they were in. Or complain that they deserved better or that they were owed the same success that someone else had achieved.

Growing up with a single mum, I learned there’s no one else. You gotta do it yourself. You need to make your own money, know how to manage it, make the decisions, and deal with the consequences.

My mother was constantly striving to develop her career, to lift herself up. With two kids in high school, working full time, and looking after her own ailing mother, Mum decided to go back to university to finish her degree after a 20 year hiatus. She studied at night, on the weekends, in the summer, and she did it while somehow juggling everything else.

As a small business owner and entrepreneur in a deeply economically depressed area, my father faced constant challenges. I watched him pivot to survive long before pivoting became Fast Company’s word of the week.

He reinvented his businesses, he developed new services, he came up with new ventures, he’d call up strangers to talk potential partnerships. Some things failed, some things succeeded but I never heard him talk about his destiny as if it wasn’t under his own control.

Watching my parents work hard and be self-sufficient helped me manage my expectations when I started my own business, and in how I live my life in general.

I get that I am captain of my own ship. I am not Rapunzel waiting for my financial partner, or the government, or the collapse of the competition to rescue me from my tower of business challenges.

It’s up to me. And with that knowledge comes a freedom, even if sometimes it’s scary. Because when you blame other people for your problems, it gives them control over your life.

And ain’t nobody got time for that.

Don’t Settle for the Status Quo

If either of my parents had settled for their lot in life, things would be very different. First of all, we’d all be miserable because they would have stayed together in a marriage that wasn’t working.

And while there was a lot of pain and challenge for everyone associated with their divorce, I believe it set us all on a track to pursuing lives that make us happy. If there’s one thing I learned from their marriage and subsequent divorce, it’s that I refuse to accept unhappiness as my status quo.

As my parents rebuilt their lives separately, I watched them try new things: new businesses, new jobs, new partners, new hobbies, new attitudes. Not everything always worked out but they never stopped trying, reaching, and believing there could be more.

My father was always an early adopter of technology and he really connected with Apple’s philosophy of “Think Different”. He’s never been afraid to try something new, like quitting a steady government job to start a new business in a totally different town.

Or calling up a big corporation to pitch an idea for a new venture. Or developing software even though he had no previous experience.

And while financial security is understandably important to my mother, she’s always been proud of the ways my brother and I have explored life and taken risks, risks she wasn’t necessarily able to take when she was our age.

Learning there is life beyond the status quo gave me the guts to quit my well-paying, steady, but stressful agency job to go freelance. It gave me the confidence to buy my own small business.

It allowed me to encourage my boyfriend to quit his unhappy job to pursue being an artist. And it helped me be open to the opportunity of returning to work full time here at Proposify.

Not accepting the status quo is critical to the entrepreneurial spirit, and it’s also the key to a happier life.

Have a Sense of Humour

Last week I spent 7 hours at the hospital with my father while he had a procedure related to a very serious medical condition. I think people in the waiting area thought we were deranged because we laughed and cracked jokes to each other both before and after his operation.

You know what my dad said to me the following morning?

“Boy, that was a fun day yesterday!”

Our ability to laugh and make fun of a situation transformed what could have been a very stressful, worrying time into a day I will fondly remember. That’s not to say I wasn’t concerned, but having a sense of humour about it made it manageable and less unpleasant.

There are times when owning a business, or being an entrepreneur, can be extremely stressful. Sometimes it’s just not fun, it’s dark, it’s scary, and it sucks.

But finding the opportunity to laugh when you can and to lighten the mood isn’t going to make things worse. It might just give you a well deserved break so you can reset and get back to killin’ it.

PS My Parents Aren’t Perfect

Don’t get the idea that my childhood was the perfect business incubator. There are mistakes my parents made (so I did the opposite!) but I’m not going to talk about them here because I want to stay in the will.

But overall, I am really grateful for the inadvertent lessons learned from both my mother and father that have contributed to my topsy-turvy and incredibly rewarding career in business.

A friend of mine started building his marketing practice with just himself and an intern a year ago, and now it’s a full-blown agency with a growing team.

We were chatting recently over a dark and stormy or two when I asked him about how he’s measuring profitability.

‘Um, I don’t really know, we’re sort of tracking time, sometimes....’

The truth is he didn’t really know his gross margins or utilization rate, so growing profitably long term will be difficult (but hopefully not after he reads this post).

He’s not alone. I struggled with this same problem when Kevin and I had our agency and since then I’ve learned from my mistakes. 

I’ve also talked to hundreds of agency owners about how they run their businesses. A common theme I’ve noticed from the most successful is to measure your key performance indicators (KPI) and use them to make better decisions.

I know metrics and math probably aren’t why you got into entrepreneurship, so leave the payables and receivables to your bookkeeper, and your taxes to your CPA. 

But as an entrepreneur or business owner, knowing your key metrics will allow you to spend more time enjoying your life and less time worrying about having enough cash to make payroll.

The following metrics fall under what I’d call acquisition, retention and profitability, or ARP if you want a goofy acronym (I know I do).

Acquisition

Number of pre-qualified leads

Hopefully you already have a system for bringing in new leads and converting them into clients.

In a given time period, let’s say, a month, how many new qualified leads are in your pipeline? Just knowing that number gives you a starting point for predicting where your sales will be in the next quarter.

The key here is to focus on qualified leads, not every tire kicker who comes looking to price shop.

How do your salespeople qualify leads? Four things:

• The lead has a problem your agency is an expert in solving.
• They have a budget.
• They have a date they want to start (like, NOW).
• There’s a fit, in terms of personality, culture, or business philosophy.

If they meet those four levels of criteria, which a 15 minute phone call should be able to determine, they are now qualified and marked as a deal or opportunity in your CRM.

As you track new leads coming in the door, make note of where the best ones are coming from. Are they referrals? Personal contacts? Subscribers of your content? Google searches?

Once you find where your best leads are coming from you can double down on what’s working.

And as you monitor the number of leads coming in each month, you can better predict your revenue. Knowing that information helps you decide whether you need to hire new employees soon, stay the course with your existing team, or lay people off (which hopefully you don’t have to do).

Number of sent proposals

It should come as no surprise to hear me say that for most businesses, great proposals are a critical part of closing deals.

Effective proposals include a strong executive summary, properly estimated scope of services, and impressive case studies.

While you shouldn’t send a proposal to every Tom, Dick, or Harriet who comes knocking, all of your qualified leads should get to the proposal stage as quickly as possible.

A common issue many companies face is that the proposals they send out sit in their pipeline for 30, 60, 90 days (or even longer!) without closing.

I’ve outlined some strategies to improve your close rate, but the bottom line is if you have tons of leads coming in but you aren’t sending proposals, something is wrong. 

Either the leads are weak and not making it through the qualification process, or your sales team is sitting on the leads too long and you run of the risk of the leads going cold.

Value of pipeline + close rate

Your pipeline consists of draft and sent proposals. In other words, proposals you’re working on, or proposals you’re awaiting a decision on.

Much like the number of leads, or number of proposals, the pipeline value helps you anticipate the coming months, for better or worse.

However, it doesn’t matter how massive your pipeline is if deals aren’t closing. That’s where your close rate comes into play.

Your close rate is simply the percentage of proposals that close. Ideally you want a big pipeline and a high close rate, but it’s better to have a high close rate.

Example: Let’s say your pipeline contains 10 deals for roughly $100,000 each. Your pipeline is $1,000,000 and your close rate is 40%. You can reasonably predict that you’ll close $400K within the next 30-60 days.

On the other hand, you might have a smaller pipeline of 10 deals for $50,000 each. You have half the pipeline size ($500K) but at an 80% close rate you’ll close the exact same in revenue ($400K) but with less effort.

While this may be simplified, the lesson is: be judicious about which leads are proposal-worthy so you spend less time writing proposals and pitching to close work, which brings us to...

Client acquisition cost (CAC)

Every business, no matter the model needs to consider their CAC.

Basic economics would tell you not to spend more money to acquire a customer than you make off them over the course of their lifetime as a customer.

While flying your team across the country to pitch a new client in person may virtually guarantee the deal, if the value of the deal isn’t many times higher than the cost, you’re going to lose money.

You calculate your CAC by totalling up all your sales and marketing costs in a given time period and dividing it by the amount of new customers you closed during that same period.

Let’s say you have 5 sales people who each make $5,000/month + 10% commission. You also spend $10,000/month on marketing, like PPC, marketing automation, and webinars, for example.

Base sales and marketing costs are $35,000. You also closed $400K in business, so the commission is another $40,000.

Your awesome sales team’s 80% close rate netted you 8 new clients, each deal being $50,000.

Your sales and marketing costs were $75,000 for the 8 clients, so your cost to acquire each of those clients was $9,375.

A CAC of ⅕ the value of the deal may seem pretty good, but if you’re in a service based industry you’re still going to have to perform the work involved in the project, or work off the retainer, to fulfill the contract — so you’re not quite in the black yet, which is why you need to focus on profit (I cover that later in this article).

Looking at your acquisition metrics helps you predict what your sales will be in a given month or quarter, you’ll know which salespeople to promote or fire, and which marketing channels to spend more money on.

Retention

Lifetime value (LTV)

A customer’s lifetime value is not the initial sale - it’s the total revenue you’ll receive from them averaged across all your clients for as long as they are clients, which could be years.

So even though the initial value of a contract might have been $50,000, you could end up making 10x that over the course of the client’s lifetime. LTV can be tricky to calculate accurately, and you need a significant amount of historical data to do it accurately.

By keeping an eye on your LTV, you can determine how much to spend on acquisition costs and  whether you are retaining customers over the long term.

To maximize LTV, you need to emphasize, encourage, and train your account managers to upsell and cross sell clients so you can extract as much revenue as possible while providing value. It’s much easier and cheaper to sell to an existing client than a new one.

And of course, I can’t overstate how important it is to keep good clients happy. It increases their lifetime value and means you don’t need to overextend your sales team to constantly bring in new clients to replace the existing ones you lost.

Profitability

Billable people utilization rate

In every agency it’s essential to track your employees’ time.

Your people are your assets, and their time is your currency. At the end of the day, you’re trading hours for dollars. This is true even if you charge fixed cost or employ value-based billing (such as the percentage of sales you generate for clients).

While it’s usual for employees to hate tracking their time, there are great tools out there like Timecamp, Tick, or Harvest that make it easier and a little less painful. They’ll probably still hate tracking time, but that’s OK, it’s how you pay the bills, and them.

Each of your billable employees (not including sales, controllers, or admin staff) has a utilization rate, which is the percentage of their time that is billable.

The best way to calculate the utilization rate is to take their billable hours — in-scope hours you can attribute to a client — and divide them by 40 hours in a workweek.

So if 35 hours in an employee’s recorded time sheet are billable, 35 / 40 gives them a 90% utilization rate.

Calculating it that way means if they are working more than 40 hours/week of in-scope work, not overages, it is possible for them to have a 100%+ utilization rate.

Give those people treats and presents to thank them, but be really careful they don’t burn out.

Next, average out the utilization rate across the whole company. You’re going to use the overall utilization rate to determine billing targets.

While you should never expect the utilization rate to be close to 100%, you do need to keep a reasonably tight grip on the metrics and push your low performers to up their game, perhaps providing a reward to people with the highest number each month.

Profit margins

This is what it’s all been leading up to. At the end of each month, quarter, year, do you take in more money than you spend?

Mad Men may have taught the world that being an agency owner is about checkered suits, office flings, and straight whiskey (not necessarily in that order), but the truth is, running a profitable agency is damn tough.

Due to the nature of the business, agencies run on notoriously razor thin profit margins, so if no one is keeping their eye closely on the numbers, the whole thing falls apart. 

You should be making at least 10-20% in profit margins at the end of the year outside of your salary, otherwise it’s hardly worth the stress and risk of running a business.

So that being said, here’s how to calculate your margins:

Sit down with your accountant and take all your monthly expenses - salaries, contractors, rent, supplies, software, food, travel, etc, - and total it up. Let’s say it’s $100,000/mo or $1.2M/year.

Your minimum goal is to invoice $120,000/mo or $1.44M/year. That leaves you with $240K in profit at the end of the year.

That’s not terrible, and it would make for a more than decent bonus, but it won’t make you rich, which is why most agency owners aim to scale their agency while keeping a healthy margin. Once you’re at $10M in revenue, 20% margins means you’re running a lucrative business with $2M in profit each year.

That aside, in this example we are looking at $120K as our target for the month.

Look at all your billable staff’s hours and utilization rate.

Let’s say you have eight billable employees. A 40-hour work week x 4 weeks per month x 8 employees = 1,280 hours. Your average utilization rate is 75%, which gives you 960 of billable hours each month.

$120,000 / 960 hours = $125 is what you need to bill per hour to be profitable. $104/hour is break even, and any less you’re losing money. If you can get away with billing $200/hour, all the power to you.

Knowing this information is crucial to running a successful agency.

When you can look at it all on a spreadsheet and know which client projects/retainers are profitable then you know which clients to phase out, and which ones to double down on.  And make sure to avoid doing things that kill your agency’s profit margins (read: working for free).

Conclusion

Of course, there may be other metrics you should be tracking and looking at on your balance sheet and P&L each month, but without being exhaustive, this hopefully gives you a starting point to using data to guide your decisions as an owner of a successful, profitable agency.

What other KPIs do you use to optimize your business?

Insightly

Our integration with Insightly will make the CRM and project management side of the sales process even easier. To connect your integration, click on Account Settings and select Insightly.

To connect the integration, you'll need your API key from your Insightly account, which can be found in your user settings near the bottom.

Once you've entered your API key, connected to Insightly, and have a pipeline, you can select the stages you want the proposal to move to as the sale progresses through the Proposify pipeline.

From here you can also import all your Insightly contact by clicking Import Contacts

You can search and choose individual contacts you want to import, or you can select them all to import to Proposify.

Now that you've set up Insightly and imported the contacts, save your settings and get winning!

When you create a proposal, a deal is automatically created in Insightly. If you don't want a deal entered, you can select that option as well. If you already have deals in Inslightly, you can link the proposal to one of those, too.

As the sale progresses you can track it in Insightly through to the finish line, access the proposal in Proposify with just one click, and download the winning proposal's PDF right from Insightly.

Zoho Integration

Integrating your Proposify account with Zoho will give you access to its plethora of business tools, namely the CRM. 

Getting started is much like the Insightly integration, you connect to Zoho by entering the API key.

Once connected, you can set up the proposal journey as it moves through the sales process. Zoho comes with preset stages, making it quick to set up.

With your stages setup complete, you can import your contacts, save your settings, and get Proposifying!

When you create proposals, you can decide whether or not you want to track in Zoho. It defaults to add them, so you don't miss out. If you have existing deals, you can link the proposal to them as well.

Now that the proposal is created you can follow the progress right in Zoho. You can access the proposal in Proposify with just one click. You can also see the proposal value and even download the PDF right from Zoho once the proposal is won.

Enhancements to Xero, Harvest, Freshbooks, and Quickbooks.

You can now add due dates and notes to invoices when created through Proposify.

Xero now let's you add a due date. 

Freshbooks, Quickbooks, and Harvest now accept due dates and notes for invoices.

Editor refinements

Over the last four weeks we have continued to refine lists, copy and pasting, and formatting. But our bug fixing never rests so stay tuned for more improvements!

Live long and Proposify,
Ricky
Proposify Product Manager

From the time I started at Proposify in July 2015 until just a couple of weeks ago, I was the only person dedicated to marketing.

Before I came on board, our co-founder Kyle handled marketing along with the one million other details involved with a start up, and then he and I worked together on some projects.

We outsourced to a local freelance designer and digital agency when we needed a little extra help, both of whom were great. But none of it was the same as having an in-house team.

I wanted my peeps. A squad. The crew.

Proposify had an amazing and busy 2015 so recently we hired five new people to help us manage and turbo-kick our growth. I was super excited that two of these new positions were a designer and a growth marketer.

My peeps! A squad! The crew!

People to strategize, brainstorm, and share ideas with on a daily basis. Sure, fist bumps some days and head butts the others, but still moving forward together with a common mission.

I’ve always enjoyed collaborating with a smart team, it was one of the things I worried about missing when I was freelancing and that I looked forward to when I came to work full time here at Proposify.

So I’m really happy that Steve Huntington came on as our new designer, and Patrick Edmonds as growth marketer.

In advance of these guys joining Proposify, I was thinking about the projects we’re going to be working on and the goals we want to achieve. I hoped that we were going to gel as a team and that we’d have a productive, effective, and fun time working together.

Which naturally led to me think about the part I had to play in this relationship, and what I could do to be a better collaborator. Because the success of this team, and how we benefit Proposify, is really going to come down to how well we collaborate.

Collaboration isn’t the same as teamwork.

It can be easy to think that teamwork and collaboration are the same thing but while they’re related, there are some differences.

Teamwork usually involves a leader who sets out an agenda and parameters. People have their distinct jobs to do within the team to contribute to an end result, kind of like parts of a well-oiled machine.

For example, here at Proposify it’s the teamwork that that we do every day that helps us achieve our mission of creating great proposal software. Each department is a team: development is coding, QA is testing, customer support is supporting, marketing is marketing, and individually within those teams everyone has their tasks and responsibilities that contribute to the team output.

But collaboration is generally less hierarchical, less structured, and more flexible. Beyond people working together, they need to think together. They feed off each other’s expertise and creativity, building on ideas to solve a problem, to create something new, or to improve on the status quo.

So for Steve, Patrick, and I, we need to figure out ways we can weave design, data, and content together to bring more growth to Proposify, improve our customer experience, and differentiate ourselves from the competition.

Be open

This sounds like a no-brainer but it’s something I think a lot of us pay lip service to. We think we’re open...as long as other people’s ideas are in line with ours or there’s not going to be much change.

I may have done things a certain way for the past year, or even my entire career, but if I’m not open to the suggestions and ideas of Steve or Patrick, it’s a waste of the expertise we hired them for. And I’ll miss out on the opportunity to learn something new.

Nothing will change, that’s for sure. Even though change can be awkward, scary, even threatening, if you want to succeed in life, you gotta “change or die.”

So we all need to be open to each other’s perspective, the way we do things, and be willing to consider a different approach.

Nothing will label you as old, behind the times, or difficult to work with faster than being that person who shuts down new ideas.

Listen

Here’s another example of something you probably think you’re already good at: listening. And maybe you are, but even when people are listening most of them aren’t really hearing what the other person is saying.

When collaborating with other people, communication is critical. A project, and even the relationship between team members, will collapse without transparent, balanced, respectful communication. And that happens by listening.

Since collaboration is about building, if you don’t listen or understand what the other person is saying, your ideas won’t have their own foundation from which to grow or be supported. You can disagree, but objections require active listening.

Find the same page and get on it

There are a million cliché analogies that can be applied to this. Everyone needs to understand what direction we’re rowing the boat, who’s driving the car, and which targets we’re gunning for. There’s likely a horse being led to water somewhere in there, too.

Nothing beneficial or productive is going to happen if people are unclear on the goals, expectations, or the final destination. And it certainly won’t be efficient.

Collaboration depends on the fact that everyone is working toward the same result and understands who’s going to do what, and when, to get there.

Do what you say you’re going to do

Ball droppers are the mortal enemies of collaboration. Not only do they threaten the project’s goals, they jeopardize relationships between team members.

While participation is key to collaboration, make sure if you say you’re going to be responsible for a task, you deliver it. And do it on time. If there’s a reason you can’t fulfill your part, bring it up with your team well in advance of the deadline so an alternate plan can be put in place before it’s too late.

No one likes to be micromanaged so if your word can be trusted and you can be counted on, you’ll be left alone to do your work, your way.

Pick your battles

No where does it say that collaboration means you have to agree 100% of the time. In fact, what’s the point of collaborating if everyone thinks exactly the same way? You’re going to disagree with someone else’s idea eventually, and you’re going to think they’re wrong. Sometimes they’re going to think you’re wrong, too.

This is probably one of the most challenging things I’ve found about collaboration. Knowing when I should really stand my ground to either push my idea forward because I think it’s the right one — or strongly oppose someone else’s position, as the case may be — and when I should just let it go.

I try hard to keep my ego out of the equation (which isn’t always easy for anyone). I never want people to think that I’m defending my idea simply because it’s my idea.

I want my idea to move forward because it’s the right solution. And sometimes I’ll say, “Maybe my idea isn’t the right one, but I don’t believe this other solution is the answer either and here’s why.”

Unless I feel deep down that this is the biggest mistake known to humans, I often let other people have their way. I may argue it, discuss it, but in the end I’ll acquiesce.

I do that to demonstrate my openness to other people’s ideas but also so that hopefully on that day when I express my strong feelings for or against something, they’ll know I’m serious. Good collaborators know that compromise is part of the process and it often leads to better results.

Don’t be an asshole

This is up there with the categories of “Be Open” and “Listen” in terms of no-brainers when it comes to collaboration (and life in general), but I am often surprised how disrespectful or negative people can be toward each other’s ideas.

If team members are afraid to speak up out of fear of being ridiculed for their ideas, you may miss out on the cure for cancer.

Again, it doesn’t mean that everyone’s ideas are good or right but discussing and analysing them is part of the process of collaboration.

If you don’t like someone’s idea, explain the strategic reasons why you think it won’t work, not just that it’s dumb. Or make a suggestion of how you can improve on the seed of that idea to get it moving in the right direction.

People don’t realize how strongly their subtle dismissals can be felt by others. This can be toxic to effective collaboration. There needs to be a feeling of a safe zone to explore ideas. Some ideas may end up on the floor and others may rise to the top but you’ll never know if they stay bottled up inside someone’s mind.

And I don’t buy into the claim that people need to have thicker skins. You’re the one with the problem if you can’t communicate without being mean.

In short: be a human, have fun, let your freak flag fly

When I was freelancing, I used to collaborate frequently with a particular design agency who was always involved in really interesting projects. Even if the projects didn’t seem interesting at the outset, they figured out a way to make them that way.

These were some of the most effective and enjoyable collaborations for a variety of reasons. To start, we were very personal with each other. By getting to know each other beyond the facade of just work automatons, there was more trust in sharing ideas, and more understanding of where those ideas came from.

We also usually started meetings by talking about something that had nothing to do with the project on the table. Maybe someone would tell a funny story about themselves, or we’d watch some ridiculous cat video, or there would be a joke. It was kind of like flushing the norm out of our brains and setting the stage to let anything happen.

There were no limitations on inspiration. A song, a documentary, another language, a book, a cartoon, a video, a news story, an animal. As long as you could connect the dots to the strategy, the idea would be considered.

Sometimes the ideas were completely out there and we all knew it, whether it was because of execution or budget or just that the client would slam the door in our face.

But sometimes after we stopped laughing, and after a sober second thought, we could see the seed of an idea in the outlandishness. We may have to round out the corners, pull it back a bit, or wrap it in a different bow, but it could work.

This is often how we ended up with THE IDEA, the solution. But this idea only happened because it was allowed to happen. People felt safe, respected, supported, and that they had something of value to contribute.

The result was a lot of happy clients, great work, and inspired team members who were hungry for the next challenge.

In my previous business, a web design agency, we always had at least one government contract on the go. Everything from universities, tourism and economic development agencies, social awareness groups, and a wide range of other public-sector clients based here in Canada.

Some projects were meaningful, rewarding, and profitable, and the clients were a pleasure to work with. Others were miserable and made us lose money.

A couple of months ago, a commenter on this post named Tricia asked:

“...lately some large public sector organizations have approached me.

I have concerns that could affect pricing in working with these different organizations. For example, the expectations around number of meetings, and dealing with different types of bureaucracy that isn't seen as frequently in small business. There are also policies and procedures that have to be understood and followed in a more structured environment.

Those are some things I can guess will influence pricing but to what extent I'm not sure. Then there will be other unforeseen issues that will come up that might compromise a project, or derail it. I'm trying to brainstorm and learn from others to help avoid problems.

Do you have any comments about these concerns since you have worked with public sector organizations?”

The simple answer to Tricia’s question is: Yes. You should definitely charge a public sector organization more money to account for the additional layers of bureaucracy.

To be more specific, here are four main ways to make sure that seemingly lucrative government project doesn’t turn into a cash bleeder.

Also check out this episode of our podcast where Kevin and I discuss this very topic.

Be selective with RFPs

This could be a whole topic unto itself, in fact, we’ve written about it before. We’ve even debated it on our podcast, discussing the pros and cons of responding to RFPs (request for proposals).

I won’t get exhaustive here but the bottom line is, are you sure this is a client you even want?

The RFP process can be a very rigid and uncompromising one in which everybody loses — the “winner”, the client, and especially all the other companies that sunk time into responding but came up empty handed.

Here are a few important questions to ask yourself before responding to a government RFP:

Will they let you call or meet before responding and/or present in person?

Sometimes in the interest of “fairness”, a public sector client won’t allow bidding companies to talk to the key stakeholders and ask questions before submitting a proposal. They’ll only accept questions by email and then send answers to all the bidders at once.

This may seem impartial, but it’s a terrible way to kick off a new relationship with a client. Hiring a service agency is different than purchasing chairs or pylons. How can the client know you’re the right company for them if they can’t have a conversation first?

Alternatively, the client should allow companies that have been shortlisted to present their proposal in-person or via web conference so questions can be answered right then and there, and both parties can get a feel for each other before signing on the dotted line.

Does the RFP prescribe solutions or require spec work?

A good RFP should outline the main objective of the project, and the key business problems they need to solve.

A bad RFP (and there are many of them) will either prescribe their own specific solutions (‘make the button red’), ask bidders to submit speculative work (like designs and wireframes), or waste time making bidders jump through unnecessary hoops (resumes of all staff, financial reports).

If a bad RFP comes across your desk, politely decline it and take all that valuable time you would have spent on the proposal to instead, oh, I don’t know, build up your lead gen system.

Sell an upfront discovery project

In this article on quoting app builds, I laid out a strategy for selling an upfront project before committing to a fixed scope project.

The same strategy can apply when you’re selling to government. Government clients want all the answers up front, so instead of putting your business at risk by overcommitting when there are too many unknowns, sell them on the idea of a smaller discovery project (small enough that it doesn’t need to go to tender) where you’ll create an in-depth scope document that lays out everything you’ll do and how much it will cost.

Then the client can shop it around or put it in an RFP. And you’re more likely to get the work if you’ve helped them get to this point.

Invest in a tight contract that specifies everything

If there’s one thing to take away from this post it’s this: don’t expect government employees to think like entrepreneurs.

If you’re working with a small business owner on a project, they’ll likely understand the concept of time = money, or that if you want more you have to pay more.

Many government employees (bless their regulatory souls) often think more in terms of black and white, on or off.

For instance, I once worked with a head professor of psychology & neuroscience at a university on a big, complicated project. She was obviously a brilliant academic, but she didn’t understand the concept of how scope change affects budget.

What seems obvious for a business person is not always obvious to someone who has regularly collected a pay cheque all their life and not had to consider where that money comes from or how it is generated.

That said, be sure to outline everything included in the contract:

• How many meetings/calls are allowable in the scope of work?
• Who pays for travel time to and from the client’s office?
• How many rounds of revisions are included per phase?

You may include this already in your contracts, but if you don’t, now is the time to start, regardless of the type of client you’re engaging with. Government clients often expect that if something isn’t directly stated then it’s included by default (weird, I know).

Hire a lawyer

Hiring a good lawyer is going to save you more money than he/she costs.

It’s especially a good time to bring in a lawyer when you’re closing a large government contract. You’ll need them to vet your contract and make sure you’re protected should the proverbial shit hit the fan.

Watch the hilarious and crusty Mike Monteiro and his lawyer talk about the importance of lawyers and contracts.

Kill fee/delay fee

You’ve probably experienced this before, when somewhere in the middle or near the end of a project, the client suddenly goes quiet.

You email, call, and leave voicemails — nothing. There’s no response and you can’t move the project forward without speaking to the client.  

One year later the client emails you: “Hey, sorry for the delay. We finally have content finalized (or whatever was holding back the project). When can we launch?”

This can happen with any client, but it can especially happen with government clients. I’ve seen it, I’ve lived it.

Make sure your contract includes what happens if the client delays the project, and how much they’ll need to pay to resurrect it if it goes dormant past 30, 60, or 90 days.

A client can’t get you to commit your resources to a project, abandon it halfway through, and then show up months or years later expecting you to drop what you’re doing and carry on as if nothing’s changed. This needs to be clearly spelled out from the beginning.

Specify when invoices are to be paid

Whatever you do, don’t say you’ll invoice the final amount when a project is “complete” or “done”.

“Done” is extremely subjective. Does “done” mean the client is fully, 100% happy with the project, it has fulfilled all their wildest fantasies, and their mom has had a chance to review it and supply feedback?

I once had a client try and hold back the final payment because social media buttons weren’t in the footer of his new website. The catch? He didn’t have any social media accounts set up, so we couldn’t add the buttons.

Instead, state in your contract that you’ll send the final invoice after a certain event happens that you can directly control, like when you make the final presentation to the client. That way even if there are changes afterwards, or if the client straight up decides to delay launching it for whatever reason, it’s clear you get paid.

Find an internal ambassador

My final suggestion is to find someone who can be your champion.

Most of the time these are internal or external consultants whose job is to help government departments find and hire the best contractors.

I’ve had a number of these relationships over the years, and these people made our agency hundreds of thousands of dollars without ever needing to pay us a dime out of their own pocket.

They gave me the inside scoop into what projects were coming down the pipe, what the budget was, and what we needed to do to win the work. Sometimes they just directly handed us projects that didn’t need to go to tender.

To find these people, it’s important to get out there and network yourself.

If you happen to meet one of these rare gems, it’s important to nurture the relationship (dinner and drinks never hurt), and there needs to be substance behind it. They have to legitimately like your company and honestly believe you can deliver the best results when they recommend you to someone else.

Conclusion

RFPs and public sector clients get a bad rap that’s often well-deserved, but there can be diamonds in the rough. Some government clients have awesome projects with generous budgets, and their internal people “get it”. But you should still take the steps outlined above to protect your business — and your sanity.

What has your experience been like dealing with public sector/government?

If I hear the word “Millennial” one more time, I’m going to lose my Gen X mind.

Don’t get me wrong, I have nothing against Millennials as people. It’s the marketing and media industries’ obsession with them that I find annoying.

If you’re consuming business or marketing news, you can’t escape reading or hearing the word ‘Millennial’ multiple times a day. It might lead you to think they’re the only demographic with a dollar to spend, a job to find, or a life worth living.

You might also think they’re lazy, entitled, and lack loyalty to their employers.

They’re either out to destroy your business by being a terrible employee, or they’re going to make you super rich if only you could unlock 'The Secret to Marketing to Millennials’.

I’m here to remind you that Millennials are simply humans like the rest of us. And your business will be much better off if you stop both fearing, or revering them.

A cohort is not a monolith

As a marketer, I understand the value of psychographics and cohorts to better understand customers and inform business strategy. Because you’re dealing with large numbers of people, often generations, you have to generalize values, needs, wants, objections, and challenges to bring them into focus.

And while I agree there are experiences and attitudes shared by particular generations within particular cultures, sometimes generalizations can make us forget that these are individual people, and we end up viewing groups like they are an immovable monolith, singular in formation and purpose.

This kind of vast stereotyping strips away the unique human characteristics of people and makes it easier for others to disregard, condescend, and discriminate. Without putting too fine a point on it, this is how prejudice works.

And if you blindly blame everything on one large, generalized group, saying things like, “I can’t keep good employees because Millennials are job hoppers”, you might be missing out on learning something valuable about yourself.

Like perhaps there are ways you could be a better, more engaged employer, or that maybe they weren’t a good fit for your company to start with, or remembering what you were like trying to establish your own career in an economy where the single lifelong job is all but extinct.

Oh, and by the way, that’s a total myth about Millennials being job hoppers.

So be careful you don’t end up using broad generalizations as a crutch to keep from improving how you do business.

You were once a Millennial, too

I’m guessing that most people reading this article are either Millennials themselves, or you’re from Generation X, like me. There may even be a few Baby Boomers out there.

While there are indeed differences in the ways each generation grew up and the context of the world as we came of age, there are actually a lot of similarities. And those similarities lie in the way that some older people traditionally describe younger people.

Like how it’s said that Millennials can’t handle authority and don’t like to be told what to do.

Isn’t that what older people always say about younger people who don’t do what they want them to?

Who likes to be told what to do? Especially when we were younger, but I also don’t know a lot of Boomers out there who like taking orders, either (shout out to my mom and dad).

Baby Boomers were famous for their disregard of authority with the protests of the 60’s and the counterculture movement. Baby Boomers were all about breaking the rules.

And apparently all of us Gen Xers are highly cynical, have a disdain for authority, and hate being micromanaged. Plus we smell like teen spirit.

I’m sure I don’t have to remind you of even one example of the hundreds of outstanding entrepreneurs, artists, and scientists over the years who thumbed their noses at convention to blaze a new trail in their field. Everyone’s favourite startup buzzword, ‘disruption’ is all about turning your back on the status quo, on the authority.

So before you let your attitude toward people be shaped by negative stereotypes, maybe look in the mirror. And look again to see how the reverse image might actually be something positive.

One more thing: Millennials are actually more willing to defer to their superiors in the workplace than Baby Boomers or Gen Xers.

Millennials make me feel like a Gen X slacker

I never really identified with the slacker title associated with Generation X, but I understood why it might seem like that’s who some of us were.

When a lot of us were coming of age in the 80’s and 90’s we didn’t know quite what we were going to do with our lives given the global economic, political, and environmental situation at that time.

My boyfriend (and fellow Gen Xer) was so affected as a kid by all the talk of the cold war and threat of nuclear annihilation, he was convinced he would never live to be 30. From that kind of perspective, you can see how life choices and attitudes might differ from other generations.

I never really knew exactly what I wanted to do as a career. I majored in Spanish in university (and that was after playing around in English and Sociology), had vague ideas about teaching, or journalism, or social work, but I was never very focused on any particular path.

I was 30 before I discovered marketing and communications and how my skills and love of writing could be used toward a career with a real paycheque. I finally found my fit.

Fifteen years later, with the exception of one Baby Boomer, I work with all Millennials. My co-workers range in age from mid 20’s to mid 30’s and they impress me everyday.

Mainly I am amazed they knew early on what they wanted to do and went after it. They are professionally skilled designers, developers, marketers, and support specialists who all have good jobs in their chosen fields.

What was I doing when I was 26?

Flailing about, whining that I didn’t know what to do with my life, working as a receptionist for a bunch of companies I didn’t respect, and writing bad poetry. (Note: no slams to amazing receptionists everywhere but I knew that wasn’t my personal destiny.)

I certainly did not have a going-somewhere job like my Proposify co-workers do, nor did I have any clue how to get there. More impressively, this isn’t even their first career job. They all came to Proposify with previous experience and industry knowledge.

Most startup founders I know are Millennials, Proposify’s co-founder, Kyle, included. Turns out Millennials are creating businesses at twice the rate compared to Baby Boomers and Gen Xers.

And I have a lot of Millennial friends who are kicking ass and taking names by doing new, determined things with their lives and contributing to their communities at the same age that I was when I taped a huge banner on the wall over my bed that said, “Life is an illusion”, as a way to escape the heartache and pressures of being a grownup.

So those “lazy” Millennials? I admire their drive, I enjoy learning from them, and I’m excited to know I’ll be able to say “I knew them when...”

Meanwhile, I’ll just be over here working on my career time machine and listening to Beck.

Don’t be an old geezer

The fastest way to identify yourself as an out of touch, behind-the-times dinosaur is to diss the up and coming generation.

Their music, their language, what’s important to them, their technology. If you automatically revert to a “kids these days” attitude when faced with something new or different from your own experiences, you’ll miss out on an opportunity to grow, and you will be officially labeled a curmudgeonly square.

That doesn’t mean you have to like everything new that comes up, but you can’t categorically dismiss it all. Generations need to collaborate  - experience and knowledge meets fresh ideas and an appetite for risk.

I’m surprised when I hear Gen Xers and Baby Boomers, especially entrepreneurs, complain about their perceived notions of Millennials, as if they were a bothersome band of misfits that can never be tamed.

I’m surprised because I think every generation’s purpose is to rebel a bit against the previous generation, and to go boldly forward. I think this because I’ve experienced it myself. Like every generation before.

If the people writing off Millennials with a huff got down off their proverbial high horses (who made YOU the standard setter?) and remembered how they felt just a few short years ago when they were trying to carve their own new path in life, they might just finally unlock “The Secret to Marketing to/Working with/Hiring/Keeping/Understanding Millennials’.

The real fountain of youth? Don’t alienate yourself from new generations or accept stereotypes that create an us vs. them situation.

Stay open to new ideas, new perspectives, and to the possibility that maybe it’s you who needs to change, not them.

Life beyond the Millennial

I know that Millennials are the generation that is currently coming of age, populating the workforce, and shaping much of consumer behaviour. There are also A LOT of them, roughly 87 million in the US alone, which can justify some of the attention being paid to them.

But they aren’t the only people with that dollar to spend, job to find, or life worth living.

It’s important to your business to diversify your understanding of human beings, not accept generalizations at face value, and to develop understanding, acceptance, and respect for people, regardless of when they were born.

Don’t get caught up in the hype of one demographic. Don’t dismiss the diversity within that demographic.

Instead of focusing on the things that separate you from other humans, search for the places you connect.

That’s where success lies.

When you’re a brand new business just starting out, perhaps with only a co-founder and an employee or two, things can be pretty easy. People iron out ideas and processes organically.

But start adding some heads to your company and you’ll find things can get more complicated and redundant, with different employees asking the same questions, and sometimes getting a different answer each time.

“What’s our refund policy?”

“What are the steps we go through when onboarding a new client?”

“Do we offer discounts? Would we add a credit or a coupon?”

“What happens if a user reports a bug?”

“What are our login credentials for testing out the Hubspot integration?”

“Who is responsible for updating the knowledge base when we release a new feature?”

“Where should I store my design files, in Trello, Dropbox or Slack?”

The redundancy of answering the same questions every week compounds for every new employee who joins your team.

This is where a team playbook (or guidebook or handbook, whatever you want to call it) comes in very handy to help streamline your business.

I recently wrote one for Proposify, and while it’s a work in progress, I thought I’d share some of what’s in it to inspire you to get a bit more rigorous with your business processes.

But first, there are some things you shouldn’t bother including.

What your playbook shouldn’t include

I didn’t want our playbook to read like the text in an insurance booklet or car ownership manual.

This is not meant to be a rule book. There’s nothing in here about HR issues, such as vacation time, or flex hours. It doesn’t contain anything about stock options or health benefits or dress codes.

The playbook is meant to be a resource for running the business. If all the founders and managers fly south to drink mojitos in a tiki bar for two weeks (Hmmmm, this gives me an idea...), the playbook can be referenced by the rest of the employees to help them operate the business in our stead.

What your playbook should include

Mission & culture

Your mission is the most important thing to internalize yourself, and communicate to your team.

In his Ted Talk, How great leaders inspire action, leadership expert Simon Sinek repeated the phrase “People don’t care what you do, they care why you do it.”

A revenue goal is a milestone, not a mission. If you say your mission is to do $10M, then what happens after you reach that goal? How do you inspire people to keep working at your company?

"A revenue goal is a milestone, not a mission."

Big, lofty, non-financial goals, on the other hand, keep people inspired even if your company is growing and making lots of money.

It’s why Facebook holds to their mission of “making the world more connected”, or why Uber wants to “make transportation as accessible as running water.” (Here are more mission statements for inspiration)

Think about why do you do what you do, what you want to ultimately achieve, and write it down.

Our playbook contains a few paragraphs about our mission and a slide deck with our brand strategy.

Customer personas

Knowing who we do it for is as important as knowing why we do it.

Understanding what commonalities exist among the majority of our customers helps us stay laser focused as we develop product features and craft marketing campaigns.

We bake customer development into our process every day, and have personas that define who our customers are. Refining these personas is an ongoing process, and we make sure everyone on the team has access to them.

Core benefits and features

As we just went over, outlining the “why” and “who” is super important, but naturally the “what” comes next. What value do we offer our customers?

We don’t include an exhaustive list of every feature we offer, but rather the core benefits of using our product, and what basic features create those benefits. Every new feature you design into the product should fall over one of these core benefits (like, save time, close more deals, streamline your process).

What if you’re a service company, like an inbound agency? Then replace “features” with “services”, but still keep them anchored under core benefits.

Pricing and billing policies

Pricing can change in any business so keeping the current pricing updated in your playbook is a good practice.

In our playbook, we include FAQs related to billing, such as how to respond to customers who want discounts and refunds, and different situations that may call for it.

Here are a handful of the common scenarios in this section:

• When a user wants their trial extended
• When they ask about how we compare to competitor X
• How to communicate pricing changes
• When they ask for their account to be cancelled
• When to fire a customer
• How to apply coupons and credits in our billing software

Customer service standards

Regardless of what type of business you run, customer service should be one of the main pillars your business is built on.

What are your standards for how your employees treat customers?

In our case, we focus our service standards around four core qualities: Empathy, speed, friendliness, and clarity. Then we outline what we measure to gauge how we’re doing, for example, average customer ratings, average handle time, or amount of replies per ticket.

We monitor the support queue on a regular basis, so if a customer has waited longer than a few hours for a response to their email marked “urgent” and no one has helped them yet, we'd push the support team to not let that slip through the cracks. The fact that our standards are documented make it easy to know what is and isn’t expected so everyone is on the same page.

We also require every employee, regardless of role or department, to do one support day each month, where they do nothing other than respond to tickets and live chats. When everybody on the team does support, everybody understands the customer, and the product, more deeply.

Emergency protocol

Do your people know what to do when shit hits the fan?

In a SaaS business the proverbial shit hitting the fan might be if you wake up to 50 emails from customers saying your site is down.

If you’re a service business, it might be if a client calls you saying their website went down right before a big event, or a marketing campaign you executed is getting major backlash on Twitter.

Whatever the case, there should be clear steps on what to do to resolve the situation. Our playbook includes these emergency steps in the event our product goes down:

1. Notify the team (guidebook lists personal email and cell number of all team members)
2. Convene on Slack #general channel
3. Respond to every customer who brought up the issue
4. Post status to Twitter - includes example tweets
5. Update status page
6. Email all customers if the issue affects more than 10% - includes example emails
7. Post-issue communication - how to handle post-mortem communication once the issue is solved

No one wants to think about bad things happening, but being prepared is a better strategy than burying your head in the sand and hoping it will never happen.

How feedback is collected and used

Especially if you’re a SaaS business, collecting and reviewing customer feedback is basically your R&D. It’s how you learn what value your product provides, and where your best customers feel it should improve.

We receive customer feedback every day from a variety of sources. People might post to Twitter, email support, leave a review on another website, write a blog post, fill out a survey… the list goes on.

@proposify Just have to love these guys. Nick told me the exact place to fix the content library issue I had. Took about 30 seconds, 🍻🍻🍻🍻🍻
— Jesse Beaty (@jessefbeaty) May 26, 2016

@proposify Can’t sign a proposal I’ve just sent out… What is this madness? “An error occurred accepting the proposal”
— Matt Davies (@matticism) May 11, 2016

Your software has made my life easy. It's almost as if you designed it for me. Just landed a project after easily building using @proposify.
— Dave Shrein (@daveshrein) May 13, 2016

We outline how feedback should be collected, organized, and managed.

We also include links to Trello where our support people can add cards for common customer suggestions.

We have a Slack channel dedicated to customer development, where we post things people say, positive or negative, that can help us learn more about our customers, their needs, and what they value most.

We use Typeform for surveying customers and Intercom to promote the surveys within our app.

It’s the job of both the founder and product manager to regularly review customer feedback and act on it.

If it’s a feature or improvement we plan on making, it gets moved to our roadmap Trello board, and once it’s ready to be built by a developer it becomes an issue in Github.

Our playbook also outlines how support agents differentiate between features, bugs, and usability issues, and how they should deal with each situation.

Development process

At Proposify we use a very loose agile methodology which consists of two week sprints. We outline our bi-weekly process in our roadmap so everyone on the team knows how the development team works.

Jonathan, our CTO, decided that due to the length required, our playbook was not the place to put in-depth documentation only our developers would be interested in, so instead he made use of Github’s wiki feature.

Here he’s outlined processes for writing and structuring code, the release process and schedule, API credentials for the various third party products we integrate with, database structure, and more.

Our playbook does reference the wiki and links to it, so those with access have a short-cut to reading those articles.

Sales process

Recently, we launched an “enterprise” plan, called Trenta which offers unlimited proposals, phone support, and a feature called “Teams”.

At the same time we launched two add-on services, one is a 60 minute training session for you and your team, and the other is where we take your existing proposal template (InDesign, Gdocs, or Word) and recreate it in Proposify so you don’t have to (both of these are included in Trenta plans).

It’s early to tell, but so far the new plan and services are working out well, but they do require more high-touch sales. An enterprise lead buys software differently from how a freelancer buys it, and requires a bit more handholding upfront, but enterprise ultimately brings more revenue and a higher lifetime value with them.

Our playbook outlines the how to sell each service when a lead comes in the door, including:

• How to validate a lead
• What information to include in Hubspot CRM
• At what point to schedule a demo and when to follow up
• Upsell/cross sell opportunities
• What the commissions are and how to track them

What’s next

We make sure the team has access to the playbook online, so it's easier to keep up-to-date than a printed document.

I’d like to make some improvements to the playbook so it evolves over time.

We should design it so it matches our new/refined brand (which hasn’t been revealed yet), and outlines some processes for the marketing department around analytics, branding guidelines, and a styleguide for blog articles — we may have more contributing writers in time.

I also want to form a better process around knowledge base articles and videos, who’s responsible for keeping them up-to-date, and when new content should be added.

But that’s the point, the playbook should be a living document that grows with your company, not a stone tablet that stagnates. 

How about you, do you have a company playbook? If not, has this article motivated you to create one? Leave a comment below.

Here at Proposify, we spend a lot of time trying to understand why our customers do the things they do, why they make certain decisions, what motivates them. But the answers aren’t always straightforward, predictable, or even rational. At least from our perspective.

We’re often surprised by the choices our customers make when purchasing certain subscription plans, how they interact with the software, why they decide to choose us over the competition, and why they sometimes decide to leave us for the competition.

We learn from testing, measuring, and experience but we still sometimes make assumptions, assumptions we think are based on rational thought, but those assumptions end up being way off.

Because as it turns out, humans can be pretty irrational.

Even you. Most definitely me.

Recently I watched an interesting documentary on Netflix called (Dis)Honesty: The Truth About Lies, based on the research of Dan Ariely, a professor of psychology and behavioural economics at Duke University.

The film explores why people lie, how they justify it, how common lying is (even among ‘good’ people), and the social and economic impacts of lying. During the film Ariely talks about the irrationality of human behaviour, which is what usually leads people to lie, and do a lot of other things.

Ariely first became interested in the idea of irrational behaviour after being badly burned in an explosion and had to spend a very long and painful time in hospital recovering. While in the hospital he witnessed and experienced a lot of irrational decision making when it came to the treatment of his injuries. Once he recovered, he was inspired to conduct research into how and why we repeatedly and predictably make bad decisions.

It got me thinking about how irrationality might also affect marketing and consumer behaviour.

I didn’t have to dig very far to discover that Ariely has spent a great deal of time thinking about, and researching, the very same thing. In fact, he published his findings in a New York Times bestselling book called, Predictably Irrational: The Hidden Forces That Shape Our Decisions.

Ariely’s premise goes against traditional theories that humans behave in fundamentally rational ways. That when we make a decision, we do it based on reason, analysis, and intellect.

Nope.

But just because we may behave irrationally doesn’t mean our behaviour is random. Irrationality is quite predictable so learning the how and the why can be extremely beneficial to business owners, marketers, entrepreneurs, retailers, and anyone who wants to understand and impact consumer behaviour.

What’s the definition of ‘irrational’?

I think a lot of times when we hear the term ‘irrational behaviour’, we imagine someone being out of control, agitated, and, well, dumb.

But Dan Ariely has a different definition and it changes the word from being subjective and judgemental to one based on relativity:

“Being irrational are the cases where we think we will behave in one way but we actually don’t. And those are the cases when people are likely to make decisions.”

I have a friend I thought of in relation to this definition. He’s super frugal, budgets his money, and I admire his financial discipline. But then I found out that in his efforts to get the best deal, he’ll drive his car to a grocery store that is at least 20 minutes away when there are lots of comparable options closer to home.

Whatever money he may save on groceries, he ends up spending on gas. By Ariely’s definition, this is totally irrational to me. It’s the opposite of how I thought my friend would behave.

You can watch Ariely explain his definition here:

So what can we learn about marketing from Ariely’s theory of irrational behaviour?

We are all under the influence

If you can convince someone to behave in a particular way, even just one time, you’ll be influencing them far in the future based on their experience, good or bad. That’s why it’s critical for marketers and advertisers to influence the first decisions consumers make about something.

We learned this lesson at Proposify. Last year we introduced a freemium plan - it had reduced features compared to the premium paid plans but it offered the very basics for creating a proposal. We assumed that this would attract people to sign-up and try Proposify and then once they discovered how awesome it is, they’d upgrade to a paid plan.

But that’s not what happened.

While lots of people did discover how awesome Proposify is by signing up for a free plan, most of them never upgraded to a paid plan. Once they had exposure to the benefits of free, once their experience with Proposify was based on free, that was their expectation. That they could get Proposify for free.

Meanwhile, lots of new customers were signing up directly for our premium paid plans, no questions asked.

You can guess what happened next. So long, freemium.

Everything is relative

Most people don’t know the value of something so they try to figure it out by comparing it to something similar, or comparing themselves to others.

That why some companies place their products or services next to similar products that are more, or less, expensive.

The value-seekers will often choose the lower priced product based on their perception of getting a deal, while the premium shopper will choose the more expensive version because they associate high price with luxury or quality.

Retail stores like Winners and Marshalls are brilliant at this. All their tags show two prices: one is the Winners or Marshalls price, and other price says “Compare at”. The Winners and Marshalls price is ALWAYS lower than the “Compare at” price, of course.

So it makes you — OK, ME — feel like I’m getting a deal with every single thing I buy. And it feels amazing.

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The fact is, I have no idea where that “compare at” price is coming from or if it’s even accurate. But they’ve planted the idea of value and comparison in my mind and I’ve fallen for it. Judging by the number of Winners and Marshalls stores across North America, I’m not the only one.

Your takeaway? Make it easy for your customers to compare value so you can influence their perception of the value your product or service.

We don’t like making decisions

According to Ariely, when it comes to making decisions, most people take the path of least resistance, even when it’s not the better choice. It’s almost like we’re making the decision to not make a decision.

By understanding your customer, you can design certain experiences to make it easier for them to decide to do what you want them to do (like sign-up for a trial or buy your product), and more difficult to do what you don’t want them to do (like cancel their account, or return the item).

This doesn’t have to be as sinister as it might sound.

For example, we try to make it super easy for new customers to discover Proposify. We offer a free 30-day full feature trial that you don’t need a credit card to sign up for so there’s no risk or obligation.

We make the process simple and quick - you can have an account in minutes. Then we provide a kick-start guide to creating your first proposal.

Obviously the thing we don’t want our customers to do is to cancel their account, to go to a competitor’s product. So we try to make it difficult to leave by ensuring they have an incredible experience with Proposify.

We focus on designing our product and our support service to fit our customers’ needs so perfectly that their lives and businesses would be negatively impacted without our tool.

We try to make it difficult to leave by becoming an essential part of their business.

Money isn’t everything, but we love free.

Often times we are motivated more by the offer of a thing itself than the money it would take to buy it.

I experienced this firsthand really early in my career when I was involved with event management and marketing.

I was an organizer for a very large charity sporting event that had a beer sponsor. In addition to cash sponsorship, the brewery donated flats of beer that we could give away to the participating teams as incentives for hitting certain fundraising milestones or other activities. Awesome, right?

There were 24 beer on each flat and at the time it would have cost about $35 to buy, which worked out to roughly $1.45 a beer.

Whenever I told the teams (each made up of 12 people) there was a flat of free beer up for grabs for any team who completed a particular task or raised a certain amount of money, there were no questions asked. They jumped to it. They took the idea of free beer VERY seriously.

I got them to wear ridiculous costumes, to register by a certain deadline, to run an all-night marathon. Anything for a flat of free beer.

But imagine the response if I had gone to each person on that team and offered them the monetary equivalent of their share of the flat, their two beers? Do you think I could have convinced anyone to do anything for $3?

So sometimes the perceived value of a thing is more valuable than the monetary value. Think about how this kind of incentive could work with your customers, like getting them to participate in a beta test, or upgrade to a more premium service.

Expectations are everything

Setting expectations can have a profound effect on how your customer perceives an experience, whether it’s a service, product, or an event.

I have another beer story to illustrate this point. (It’s noon somewhere, right?)

I don’t like ‘hoppy’ beer. A few years ago I attended an event at a local Halifax micro-brewery. I was familiar with a number of their brews but found them too hoppy for my delicate palate. I didn’t like the taste.

So when I went to the bar and they had several choices on tap, I told the bartender I didn’t really like hoppy beer and asked for a recommendation.

He poured me a sample and said, “You’ll find this beer really tastes like grapefruit, it’s quite fresh and tart.”

I love grapefruit. I sipped the beer. It did taste like grapefruit! The beer was yummy for the rest of the evening.

But when I tried the beer again on another occasion I realized that hoppy actually tasted like grapefruit.

It was the very same beer that I had previously found ‘hoppy’ but by changing my perception of the taste, and he wasn’t lying, the bartender changed my perception of the beer.

I still don’t drink that beer regularly but when I do, I always think ‘grapefruit’ before I take a frosty, thirst quenching sip.

Establishing and communicating expectations, both positive and negative, helps you manage the consumer experience.

Make it easy for your customers to find positive reviews of your product or service while they’re in the decision-making process.

Offer a glimpse of how bad things could be without your product or service.

This is where good branding can do a lot of heavy lifting and why it’s critical to craft clear, compelling messaging.

Your brand creates the expectation, it communicates a beneficial promise to your customers. It prepares them for the experience of interacting with you and your company.

Focus groups aren’t that great

I’ve lost track of who’s winning the ping pong battle over the value of focus groups, but Dan Ariely is definitely lobbing one over the net with his research.

As a result of his work in human behaviour, Ariely has little confidence that people are able to understand their own decisions. Which is why he doesn’t put a lot of stock in the results of focus groups.

“One of the things that I think companies do to a large degree that makes very little sense, is the use of focus groups.

So think about what a strange idea is that we take 10 people who know basically nothing about your project and you put them in the room and you let them talk for a while and then you take the, whatever they came up with, as a consequence of these two hours of random thinking and you base your strategy on it, to a large degree.

And I don’t want to say that focus groups are always useless and also uninformative, but I think that taking this data and then relying on it as extensively as companies do, I think it’s crazy in many ways.”
–Dan Ariely

Instead of asking people for their opinions, run experiments and observe real-time, real-life behaviour, not subjective reflection.

I’m OK, You’re OK

But we’re all irrational. The key is to accept that irrationality influences how your customers make decisions about your business, how they interact with your brand, how they talk about you on social media, and how they decide to stay or go.

Your challenge is to learn how to predict irrational consumer behaviour so you can harness it into an opportunity.

The Rational Choice is Dan Ariely

I highly recommend checking out Dan Ariely and his research. This post just scratches the surface of his fascinating exploration of human behaviour and there’s so much more to learn. I got lost down a lot of interesting wormholes while working on this.

He’s a really engaging speaker, you can check him out on any of his six Ted Talks and he is a clear and compelling author of four books.

Let’s wind the clocks back to 2007.

I had a young family, including a newborn son, and was working full time as a designer at an agency. I was sick of the 9-5 and wanted to be my own boss, so I started taking steps to build my client base and go freelance.

It involved a lot of late nights grinding out on freelance work until 3 a.m., then waking up to start my salaried job for 9 a.m.

After I finally quit my job to start freelancing full time, I expected I’d be working fewer hours and making more money. While the latter was true, the former certainly was not — I was making more money but I was working long hours from around 9 a.m. until sometimes 2 or 3 a.m., with breaks in between for food, meetings, or family time.

The more I worked, the better I got at my craft, the happier clients were with my work, and the more money I earned. I got a bit obsessed.

Less than a year later I got tired of being a lone wolf, so Kevin and I teamed up to form Headspace, a web design agency. I was really excited to have a partner and begin hiring employees. Now finally there would be no need for me to work as long or as hard.

But I still did the late nights, working 'til 3 or 4 a.m. to get a project done, a proposal written, or a content piece to promote our agency. I’d sleep until mid-morning and then start work which just meant I had to work even later to get everything done.

After years of hustling, I finally burned out.

Despite all that grind, we were still constantly wrestling with cash flow from poorly scoped and managed projects and late paying clients. Combined with personal trauma and the lackluster performance of our business, I was practically running on empty and had no energy left to move ahead.

Fast forward to today

We sold the agency in 2014 and raised a small seed round of investment to focus on Proposify.

Within four months we had hit product/market fit and could begin scaling our efforts. About a year and a half later we reached $100,000 MRR and are profitable.

So what happened? Was it the result of hustling for long hours, days, evenings, and weekends?

Funnily enough, it was the opposite.

For the past couple of years I have generally worked about 8 hours (give or take) a day during the week.

My evenings are either spent with my two sons when I have them, or out spending time with friends. If I’m home I watch Netflix after 9 p.m. Sometimes I read articles or just waste time on social media. I may answer some work emails or a couple of support tickets.

Then I wake up at 8 a.m. and start my day, usually heading into the office around 10 a.m. and leaving around 5:30 p.m.

I don’t usually work weekends, although Sunday evenings I do like to prepare my schedule for the week.

And yet despite my very typical, maybe even relaxed routine, I am further along as an entrepreneur than ever before, and our business has been growing consistently for the last year and a half.

Why?

“Lazy” Leadership

I recently read this post by Andrew Wilkinson, the founder of MetaLab, a very well-regarded design agency in Vancouver.

Titled Lazy Leadership, his post echoes my thoughts exactly when it comes to leading a company.

Like me, Andrew doesn’t work overly long hours. In fact, he doesn’t even start working until noon and he rarely goes into his office.

And yet, across his companies he employs over 200 people and has invested in 30+ companies. MetaLab also designed a little app you might have heard of called “Slack”.

Clearly, his style of leadership works.

As entrepreneurs we want to build great companies without sacrificing our health, family, friends, or happiness to do so. And that’s entirely possible, as long as you focus on the right things.

If you run an agency it’s worth checking out Andrew’s post on Medium, but here are my recommendations for lazy (read: smart) leadership when building a product/SaaS company:

Focus every day

I sometimes wonder when people say they work 12-15 hour days how much of that time was spent doing important work and how much time was spent mindlessly switching between tasks and Facebook.

When I know I only have a set amount of hours to work, something wonderful happens: I waste less time. I’m not going to say I don’t waste any time during the day, but I focus more when I know that work ends at a certain time.

Here are my tips to be more focused and productive:

• Have a short list of important tasks or outcomes you want to accomplish and check them off as you complete them.
• Do one task at a time, focusing on the hard stuff first when you have the most energy.
• Close down all distractions, like email, Slack, and social media until you get it done. Don’t answer people’s texts unless it’s an emergency.
• Keep meetings short and productive.
• Don’t drive to work if you can help it. I walk and take the ferry most days and use that time to read, think, and reflect so I can double down once I get into the office.

Make good use of technology

Technology goes a long way in freeing you up to get more done in less time. Here are my favourite apps and I how use them:

Evernote

I use Evernote for weekly task lists, but I also use it for nearly everything else: budgets, feature ideas, customer calls, blog or podcast notes, you name it. My entire life goes into Evernote.

Pocket + Buffer

Throughout the day I come across articles that I want to read, but don’t necessarily have the time at that moment. Instead of keeping tabs open I use the free Pocket app and its associated Chrome extension to save it to Pocket and read it while I commute to work, or just before bed.

If the content is worth sharing, Pocket lets you add it to Buffer to distribute throughout the week. This way I am not using work time to read and share content.

Fancy Hands

I absolutely hate calling around to make appointments or to get quotes from suppliers. It’s time consuming and distracts from important work.

I just started using Fancy Hands and have to say I love having a “personal assistant” who can do all the annoying chores that I hate, and how it frees up my day to focus on important tasks.

Google Calendar + Calendly

I recently moved from iCal to Google Calendar, and after figuring out the quirks, my calendar is a lot more organized and streamlined. Kevin and I each have two Google accounts, one for work and one for personal use. Kevin and I share our calendars with each other, so we can see who is busy when.

Then we use Calendly when people want a phone call or when scheduling podcast interviews. It shows the person our availability and then once the meeting is booked it goes right into the shared Google Calendar.

This saves so much back-and-forth time with people trying to nail down times.

Mac Mail Rules

Email is a necessary evil, and far too much time is spent reading, organizing, and responding to emails. I hate having an out-of-control inbox, so I use rules in Mac Mail to organize my inbox for me.

Notifications from various tools our team uses (Groove, Trello, Slack) are set to automatically go into their own folder. Newsletters I subscribe to, social media notifications, and invoices/receipts each have their own folder and accompanying rule.

This makes it so the only emails that go directly to my inbox are emails I need to read and reply to. I keep all those messages in my inbox, and unless they are time sensitive, I only take an hour about once or twice per week to reply to all of them at once instead of breaking my day up being distracted by every incoming email.

That means most people don’t get fast responses when they email me, and maybe that’s ok.

All of these tools and systems help me focus each day on important work so I don’t have to spend hours on repetitive tasks that force me to work extraordinarily long hours.

Build a machine

In the aforementioned post by Andrew Wilkinson, he talks about how he thinks of building a company like building a machine, something that functions and produces results without much manual labour.

If I look at Proposify under this framework, the machine has a few things it needs in order to produce a successful result:

• A steady stream of new customers who start a free trial, understand the value of using our product, and upgrade to a paid account at the end of their trial.
• Happy existing customers who stay with us, gradually pay us more money over time as they experience success using the product, and promote us to their colleagues.
• Technical infrastructure in place to keep pace with growth.

To accomplish these three things our machine is built with the following components:

• Marketing to analyze each stage of the marketing funnel, drive qualified traffic into it, and convert leads into customers.
• Customer success to help people understand the product, and deliver happiness to them by listening to and solving their problems.
• Product team to understand what the market needs and execute the vision to help grow the business.
• Engineering to improve the quality, speed, stability and security of the product and infrastructure.

When I had my agency, I worked long hours doing things I could delegate to employees, like performing billable client services, managing projects, and writing proposals. Instead of working on building a machine, I was a cog in my own machine.

Now with Proposify, I tend to work at a higher level, on the machine itself. I am still involved in a lot of the more detailed aspects of the business, like creating content, overseeing product features, and providing input, but in general, I leave the detailed work to the pros I hired and try to stay focused on activities I’m better suited to.

When someone asks me to do something for them because they’ve never done it, I sit down and show them how to do it themselves so they won’t need to ask me again. Teaching them how to fish keeps me lazy for a lifetime.

High-impact activities

Naturally it depends on what kind of business you run, but I think in general the following activities are what every business owner should be focusing their time on:

Building the team & culture

Our culture is founded on the following principles:

• Customer service is the foundation of our company, and it's the job of every team member regardless of title.
• We're building more than just software. We're helping our customers sell smarter and be more successful.
• There are no silos or egos around here. Product, marketing, and customer service all communicate and help each other to make the product better.
• We are all about mutual respect, cooperation, and a good joke.

As the CEO and co-founder, it’s my job to make sure these principles are baked into the foundation of the company, and to hire team members who fit into this culture, nurturing them to do better, and challenging them to grow.

Hiring is one of the most important tasks for a startup CEO to perform. I laid out our hiring process in a recent blog post, and the tool we used to make it more streamlined.

Naturally when you’re starting out, before reaching product-market-fit, you can’t necessarily afford to hire a lot of people so you need to wear more hats, doing product, support, marketing and whatever else is needed.

That doesn’t mean you need to kill yourself and risk burnout by hustling 14-hour days, it just means you need to focus your time on what matters now, and either outsource the rest, or leave it alone until you can tackle it. (For the record, we don’t pressure our employees to work overtime either.)

Understand customers

I spend a decent chunk of my time every week doing customer support and customer development.

I’ve ripped off this exact approach from Alex Turnbull of Groove, and it’s worked incredibly well for us. After every person signs up to a free trial of Proposify they get this email:

I read every email that gets sent my way and respond to it. Then I log it to our customer development channel in Slack so the whole team can easily read through it, search it, and leave comments.

60 days after every customer signs up to a paid plan, I send out another email:

If a customer books a call through Calendly, I have a 15 minute phone call to get their thoughts on how Proposify is working for them. Then I leave their comments in Evernote and add it to the Slack channel so it can be viewed by the rest of the team.

All this customer support and development keeps me connected to our customers and the product so that I don’t lose touch, allowing me to help the product team plan and design new features.

In addition to talking to customers I also make a point to use our product, signing up for a new account every month or two, and going through the onboarding process to see it from a new user’s perspective.

Expand your network

Without a doubt, our podcast, Agencies Drinking Beer, has been one of the most successful experiments we’ve tried, and has been a great way to connect with customers, build our personal and professional brands, and develop lasting relationships with influencers.

In addition to the podcast I sometimes appear on other people’s podcasts, blogs, webinars, and speak at events, which helps spread the word about our company and helps expand my professional network even further.

I’ve applied some of the tips on influencer outreach from Alex Turnbull at Groove.

For example, start out by offering value to an influencer. Our podcast helps because it’s easier to ask someone to be a guest on our show, which both flatters them and offers them added exposure.

Other ways might be following their blog and leaving meaningful comments, attending events they are at, or asking a mutual connection for a warm intro.

Once you have a relationship with someone who can help spread the word and have offered them something of value, then make the ask, whether that’s doing a joint webinar or guest writing for their blog.

Build processes

Processes are like recipes. If something in your business works well, then formalize it into a process and add it to your company playbook, so that all team members are on the same page and can replicate that success.

If they come up with ways to improve that recipe, listen to them, try it out, and see how it works, and if it’s successful then make it official canon.

One example is how we decide on new features (ie: product management). It’s not down to a science, but using this chart helps us decide which features will have the biggest impact on our business.

There’s more about this in a post I wrote that walks through some of our processes as we scale the company.

Track results

If you’re going to build a machine you need to make sure it’s actually performing and doing what it’s supposed to.

The best way to do that is by tracking KPIs - or key performance indicators - so you know when the machine is improving, and if not, you can try to figure out why.

Metrics agencies want to track include close rate, utilization rate, gross margins, and more.

SaaS metrics include visitor-to-trial conversion rate, conversion-to-paid, net MRR churn, lifetime value (LTV), and average revenue-per-account (ARPA).

I keep a close eye on these metrics on a regular basis, and work with our growth and product teams to brainstorm how to improve those numbers.

These are the core activities I focus on every week. Also check out 7 activities business owners should do every day. If I stay focused on the important tasks and delegate or automate as much of everything else as possible, then I don’t need to burn myself out working evenings and weekends.

Conclusion

Frankly, I’m getting tired of articles like this one that have practically become part of my daily Medium feed.

They say (or imply) that unless you hustle 12-15 hours/day, skip your favourite TV shows in favour of reading business books, and wake up at 4 a.m. to workout before starting your daily grind, you’ll never achieve financial success.

I’m not saying that I couldn’t stand to get up a little earlier, workout a little more often, and drink a little less. Those are definitely personal goals. But entrepreneurs need to stop putting so much pressure on themselves to become superhuman embodiments of self-denial.

I’ve lived the hustle, spent most of my time working, and it didn’t make my business any more successful, it just made me more unhealthy and unhappy.

For the past couple of years I have lived well, working moderately, smartly, and efficiently. I took a vacation for the first time in half a decade. I spend a lot of time with my family and friends. I’m not Bill Gates, but I’m a lot more successful, and happier, than I was before.

So take care of yourself. Live your life. Love your work, but don’t put it above family, friends, or happiness.

Now get out there and keep killing it.

Because I’ve been involved behind the scenes in so many pitches and proposals over the years, when I watch ads on TV or online, I’m usually not thinking about the product they’re selling, I’m wondering how the agency convinced the client to go with that concept.

Regardless of whether I think it’s a good ad or a bad one, I’m curious how the agency persuaded the client to choose that particular direction because selling your ideas to people is difficult. Especially if it’s something that involves taking a risk or is unusual, like the rainbow-pooping unicorn concept of the Squatty Potty video.

Like, what went on in that pitch? (I think this is a brilliant way to sell an icky subject, BTW)

We’ve probably all been in situations where a potential client chose a competitor even though we know we would have done a much better job, but somehow they were convinced that the other company was the best choice.

When it comes to proposals, it’s not always the most qualified company who wins, but the most convincing company.

Being persuasive is the key to successful sales. It’s about inspiring people to buy, to care, to spread the word.

In this post, I’ll try my own hand at persuasion by sharing a few tips on how you can write proposals that convince and convert.

Qualify Your Lead

If your potential client isn’t a good fit for your company to start with, they’re not actually serious about doing business, or they don’t have an appropriate budget, you’re not going to be able to convince them of anything, and you’ll just be wasting your time.

Validating your leads before you spend hours preparing a proposal is probably the most crucial step in sales. Figuring out if this potential client actually has potential should be your first step in the sales process, before you even type one little word of your proposal.

To help with that, here are 5 things to ask yourself when talking to a lead to see if they’re worth pursuing:

1. Is this my ideal client in terms of industry, size, or revenue?
2. Can I/my team really help them solve their problem?
3. Am I truly excited about this project?
4. Does this client have a budget I can work with?
5. Is there a personality fit? You don’t have to turn into BFFs but if there isn’t some connection, you might have problems once you start working together.

By confirming that this client is actually a good fit for your business, you’ll have a much better chance of convincing them to choose you.

Answer the question, “WHY?”

This is really is the crux of all persuasion but I’m surprised how many proposals don’t directly and clearly address it. People don’t like to be told what to do without a good explanation, so you need to guide them through that.

Every proposal should answer these ‘why?’ questions:

1. Why is the client looking for help?
2. Why should they choose your business?
3. Why shouldn’t they choose the competition?
4. Why is your solution the right one for this client?
5. Why should they trust you?
6. Why are you the expert in this situation?
7. Why should I spend this much money when it’s more than what the competition is charging?

When preparing your proposal, you need to think of every ‘why?’ that might emerge that could derail your efforts of persuasion, and be sure have a compelling answer.

Understand the client

To convince anyone of anything you first need to establish that you know something about the situation. Make sure your proposal demonstrates that you understand the client, their business, their customers, their industry, and the challenges they’re facing.

This involves listening to the client, doing research, and directing the proposal to focus on the client, not you. I don’t know how many proposals I’ve read that were just all about the agency or business - me, me, me, and more about me - with very little attention paid to the actual client and their problem.

Proving you get it, and them, establishes credibility so the client’s more likely to be open to what you have to say and more easily convinced that you know what you’re talking about.

Make Your Case, Consistently

If you want to persuade someone of something, you need to be clear about what that something is and be consistent in defending and proving that point throughout your proposal.

People are very suspicious of others who appear inconsistent in their views and opinions. Sometimes the very the act of changing your mind (justifiably or not) can be viewed negatively by others, as if you don’t have the fortitude to stick to your guns, or that you had poor decision making abilities the first time around.

Be straightforward with your position and keep proving it over and over throughout your proposal using storytelling, stats, and other proof points to drive it home.

Being consistent is also a form of repetition which is another effective persuasion technique. People need to hear something more than once to really absorb what you’re saying and adopt the same view.

This will establish trust with the client and if they trust you, they’re more likely to be convinced by what you say and that you’ll deliver on your promises.

Problem, Agitate, Solution

Also known as PAS, this is a classic copywriting formula and persuasion technique, perfect for writing a convincing proposal.

As discussed earlier, it’s important that you show the client you understand the problem or challenge they’re struggling with.

The next step is to agitate the problem, making it a little more painful, demonstrating how dangerous the risks are if the problem persists, and how crucial it is to find a solution.

This isn’t about fear mongering but again, showing that you understand the pain, you have experience with it, and you want to shelter the client from it getting much worse.

Then you swoop in with your brilliant solution that will make everything better, alleviate the pain, and save the future from certain demise.

An exaggerated and often hilarious example of this technique is regularly used in those gadget commercials on TV, like this one for Wraptastic.

Life before Wraptastic is grey, frustrating, wasteful, and time consuming. Then along comes Wraptastic and life is in full colour, everything is easy, and not only will I be able to wrap 3 hero sandwiches in 5 seconds, my hands will be safe from the shark-like aggression of the teeth on the average food wrap box.

Obviously, the way these gadget companies use PAS is waaaaaaay over the top but you can adapt this formula for your own clients and services in a way that is relatable, professional, and convincing. AND TRUTHFUL.

Provide Social Proof

We are social creatures who want to fit in, be accepted, and be associated with the same characteristics as the peer group we admire.

You see this with the rise of influencer marketing. That person I think is smart and successful said this product or service changed their life, saved their business, made them better looking. So because this ‘expert’ said it was awesome and I have the same problem, I’m going to try this product, too.

Integrate case studies (I prefer the term “success stories’, more persuasive language), testimonials, reviews, and referrals in your proposal to help build your case that your solution is the right one.

And don’t worry, you don’t necessarily have to have Gary Vaynerchuk or LeBron James pimping your services, you just need other people and businesses your clients can relate to who talk about how you solved their problem.

Tone of Voice

Regardless of the message you want to communicate to your potential client, they’re not going to understand or relate to it if you don’t speak their language, or if you use a tone of voice in your writing that alienates them.

While you want to establish yourself as the expert in your proposal, you don’t want to come off as condescending to your client, or imply that they are idiots for not coming to you sooner.

Avoid using jargon and other overly technical terms your client won’t understand. It doesn’t make you look smarter, it makes them feel excluded. More importantly, if they can’t understand what you’re talking about, they won’t be persuaded by what you have to say.

Establishing a relatable tone of voice in writing your proposal will help to emotionally connect with your clients, and emotionally connecting with your clients is another persuasive technique.

Is your tone professional, conversational, empathic, educational, or irreverent?

Think about your clients - who they are, what they value, how they see themselves, and how they want to see themselves in relation to your service or product. Choose a tone of voice in your writing that speaks to them, while still being on brand for your company.

Use Plain Language

Plain language writing is about just that — writing in a clear, concise manner so that readers easily and quickly understand what you’re trying to convince them of.

It’s also known as plain English in some circles but whatever you call it, it’s about removing all ambiguity, convoluted language, and jargon from any document.

Making sure your proposals are as straightforward as possible will make it easier for clients to be persuaded. They’ll understand what you’re offering, what the process will be, and what results they should expect.

Plain language makes your proposal easier to understand, easier to remember, and easier for the client to say yes.

You can read a post I wrote a few months ago that outlines the importance of plain language in sales and how to incorporate it in your proposals.

Design matters

Your products and services may be superior compared to your competition but if they don’t LOOK superior, it’s going to be hard to convince your client otherwise.

Making your proposal legible, aesthetically pleasing, and professional looking will go a long way in persuading a client that you are the best choice, regardless of the actual words you use.

Here are four basic rules to follow when designing your proposal:

• Don’t cram every page with text.
• Use whitespace and beautiful images to let the design breathe.
• Make appropriate use of color.
• Use legible and elegant typography.

If you need help, hire a professional to design your template and follow their guidelines, or start with a well-designed stock template ( may I offer a few suggestions? ) and make it your own.

Creating the win-win situation

Being persuasive comes down to gaining the trust, and respect of your potential client so that they are easily convinced by the solution you offer them.

You want to address all their concerns so they feel there little risk in their decision to choose your business, and leave them feeling confident about themselves and the future of their company.

Learning to sell and write more persuasively can be the tipping point for converting more proposals into closed deals. And more closed deals help convince more clients.

In many ways, it’s the perfect symbiotic relationship; SaaS companies need to acquire and retain a high volume of paid subscribers at a low acquisition cost.

Agencies want a consistent source of quality clients and additional revenue streams.

Enter the software/agency partnership.

What is a software/agency partnership?

Big, complex pieces of software often require a lot of handholding that they simply can’t provide to all of their customers.

If they want to acquire customers cheaply and retain them longer, they need digital agencies as partners who can do all of the sales and training for them, building in their own consulting fees on top.

The SaaS company feeds their partners leads and empowers them to focus on what they’re best at, while the agencies act as sales agents for the software company, recommending it to their clients.

Becoming an agency partner requires heavy investment to learn the intricacies of the software, going through training courses and paying fees to the software company to be formally recognized or accredited as an official partner.

While there are a lot of companies I could talk about by way of example, I’m going to focus on three distinct software companies, all of whom partner with digital agencies: Hubspot, Shopify, and Infusionsoft

Note: this post is not meant to sell you on becoming a partner of any particular software platform, or partnering with anyone at all. It is simply meant to outline the pros and cons of taking your business in this direction.

First of all, let’s review the benefits of being a partner:

The benefits of partnering with a SaaS platform

Most agency partners start out as general web design or marketing companies, and after using the software, either for a client project, or for themselves, they decide to take the plunge and completely rebrand their agency as, say, a Hubspot-Certified Partner, or Shopify Expert.

Often what drives agency owners to make this kind of drastic, expensive decision is the fact that the agency business is tough. It’s hard to sell monthly retainers, and it’s hard to specialize in a niche. Partnering with a growing SaaS company can help them take their business to the next level.

Here’s how:

Steady source of leads

Lead generation for agencies is tricky, and it’s one of the most common problems agency owners tell me about.

One of the perks of being a certified partner with a big software company is that you get listed in their marketplace or directory.

Do these partner directories actually work at driving leads to agencies?

In this video, Kurt Elster from Ethercycle says that previously when his company was a generalist, they’d be lucky to get 6-10 leads in a month.

Now as a Shopify expert, they sometimes gets 10 leads per day — more leads than they can handle — and they are not even listed as a top Shopify expert!

This is the power of specialization at work, along with being part of a big network.

As another example, I spoke to Jim Hohl, the CEO of Visify, an Infusionsoft partner out of New York City. He said:

“We had been using Infusionsoft for some time but we wanted the official stamp of approval as a way to distinguish ourselves from the competition. We also wanted to have more of an impact on the development of the software which is so integral to our business and our clients' businesses. Being a partner gives us social proof and access to the important players at Infusionsoft, which has been the biggest benefit so far. Together with them, we have set up a series of events co-hosted with Infusionsoft and I expect a decent number of leads to come from them.”

Expand beyond the local market

In every instance where I’ve spoken to agency owners who partner with a software platform, they told me that when they were generalists they were limited by their geography, but now that they specialize they have clients all over the world.

When you’re a generalist, you’re often limited to working just with local clients, and that can make life pretty tough when you live in a small city where the client pool is equally small.

But clients who are looking for a very specific type of agency generally don't care where the agency is located, they care about the results you bring.

Guidance and mentorship

All of these software companies rely on quality agencies selling their product to their clients so they offer plenty of help and guidance to ensure the agency knows the software inside and out, and is selling it effectively.

In addition to videos and guides listed in their academy, Hubspot offers an onboarding program for agencies that includes a “channel consultant” and a “channel account manager” who assist with training, technical setup and support, and guidance on how to package and sell Hubspot to clients.

InfusionSoft offers their partners one-on-one training, forums, and even weekly and quarterly business reviews.

Shopify offers workshops, webinars, marketing materials, and private forums to help their agency experts stay on top of their platform.

A sense of community

When you’re a partner with a software platform, they have a large community of other partners all drinking the same kool-aid.

In addition to online communities, nearly every SaaS platform that relies on third-party partners to resell their software, hosts some type of conference.

Last year, my cofounder and I attended PartnerCon - Infusionsoft’s partner conference.

Hubspot and Shopify also have Inbound and Unite respectively.

While some may view other partners as competition, the consensus seems to be that agency partners view each other as colleagues, often referring clients to each other and sharing ideas and strategies.

Reduce risk and overhead

When you build your own software to sell to clients, you are solely responsible if there are bugs or downtime. Maintaining your software is a massive, ongoing cost to your agency.

The beauty of reselling proven software is that you can focus on what you’re best at, like marketing strategy, consulting, or design, and leave the heavy lifting to the software giants who have hundreds of developers, product managers, and QA testers working on it every day.

This also has a downside (see later in this article where I list the caveats).

Additional streams of revenue

In addition to getting more clients, agencies also benefit from partnerships by generating additional revenue, in many cases, passive, recurring revenue (the best kind).

If you’re a skilled designer or developer, you can build your own apps and themes  and then sell them on the Shopify and Infusionsoft marketplaces.

I interviewed Aaron Whitman from Able Sense Media a while back, whose agency is a Shopify expert. They built two apps for Shopify that extend the core functionality, and the app downloads through the marketplace generate thousands of dollars in recurring monthly income.

Another example: a couple years ago I interviewed Jeff White from Kula Partners, who had recently re-branded his agency to be inbound/Hubspot focused.

At that time, Kula wasn’t even yet a platinum certified agency partner, but even then their pivot drove their recurring revenue by 1,066% in one year (it made up 35% of their total revenue, and even more so now).

A big part of this is because Hubspot trains their agnecy partners to sell and package their offering into retainers. They know that users of their software will be retained long term if they have an agency holding them by the hand and guiding them every month, so it’s in their best interest to teach agencies how to sell retainers.

Potential drawbacks/considerations

Do you want to be tied to one solution?

Many agencies want to be “solutions-agnostic” so they are not tied to any particular piece of software, instead recommending the best solution for the client’s needs.

Becoming a certified agency partner generally means you only sell that software, and don’t recommend or implement any other competing software.

If you’re a Shopify Expert, you’re likely not going to recommend Magento or BigCommerce to clients.

The other thing to consider is that when you recommend third-party software to your clients and it doesn’t deliver results, they experience a bug, or they need a particular feature not offered, the client may hold you accountable as the company they trusted, even though you are completely powerless to fix or improve the software yourself.

Can you stand out in the marketplace?

Having a large community of other partners has its benefits, but it can also be a double-edged sword — you may be competing with those exact same agencies for the same client.

You’ll need to make sure that knowing a particular piece of software isn’t the only benefit you bring to the table.

Specializing in a vertical market can really help with this. If you are a Shopify expert who also understands the packaged goods industry in depth, no one else will be able to touch you when you pitch Kellogg’s on a new ecommerce store.

Can you invest the time and money?

This holds a lot of agencies back from taking the deep dive into partnering with a software platform — it’s very expensive!

For example, becoming an Infusionsoft partner will run you about $1,000-4,500 in upfront fees, and renewal fees in the neighborhood of $250-$3,000.

Hubspot requires many hours of training to get certified in a variety of different topics around inbound marketing. Paying your staff (and taking the time yourself) to get trained takes time, which as we all know equals money.

Jim Hohl, mentioned earlier, said about Infusionsoft, “In addition to the classroom time, the assignments were very thorough and it took time to do them right.”

Using Google as an example, I asked Andrew Breen, the CEO of PPC agency Outshine about what it’s like being a Google Partner:

“Being a Google Partner is free, but you need to meet certain criteria around training and ad spend. The training criteria is time consuming as they need to be updated yearly, there are 6 exams, and you need an 80% to pass an exam.”

Bottom line: if you’re an agency struggling to keep the lights on, you may want to wait until you’re on stable footing and have some extra cash in the bank before making such a huge commitment.

Is the company stable and future-proof?

When you brand your company around one particular software platform you better be sure that it’s an established, robust company that’s still going to be around for the next five years and doesn’t get usurped by a bigger and better technology, otherwise you’ll need to reinvest all that time and money again in learning the new industry standard.

For example, in our podcast interview with Jason Swenk, he said that over a decade ago all of his competitors were specializing in the CMS, Sitefinity. I’d be surprised if anyone reading this knows what that even is, as it’s fallen by the wayside a long time ago.

Now, if you’ve chosen the three examples I’m focusing on for this post, you shouldn’t need to worry:

• Hubspot IPO’d in 2014 and did over $180M in revenue in 2015. [Source]
• As of 2015, Shopify is a publicly traded company with revenues in excess of $200M per year. Even Amazon closed down its webstore service and recommended its merchants migrate to Shopify. [Source]
• Infusionsoft hasn’t IPO’d, but even as a privately owned company, it did $80M in revenue last year and has raised over $125M in venture capital. [Source]

However, just because a company is on top now doesn’t mean it will last forever, and that needs to be considered when choosing a platform to build your own brand around.

Conclusion

Making the choice to specialize in and partner with a software platform is a big decision to make. Hopefully this post helped lay out the pros and cons. If you run an agency and have (or haven’t) made the plunge, or are thinking about it, I’d love to hear your comments below.

When it comes to sales and marketing, I’ve spent the majority of my career on the marketing side, either working at an agency providing support to businesses, or as a freelance consultant in branding, communications, advertising, and strategy.

It was always a bit of a Debbie Downer moment when our team would present a strategy or campaign or something we thought was super smart to the client (usually the marketing team) and they would agree, “That’s super smart!”, but then later in the meeting someone would inevitably say, “But I don’t know if the sales team is going to like it.”

Or worse, the client would leave the meeting and us with the feeling we had hit the nail on the proverbial head but three days later we’d hear, “We’re having trouble convincing sales that this is the direction to go in,” or “Sales doesn’t get how this is going to help them reach their numbers.”

Occasionally someone from sales would attend a meeting where we’d be talking about a brand strategy or something else “market-y” and the body language from that person was rarely encouraging. “That’s nice, but how is it going to help me convince my customers to place larger orders?”

They were always the toughest, most skeptical nuts to crack in the room. I often felt they were missing the point, fixated on numbers, and unable to see the bigger picture.

So over the years, I started to think of sales teams as party poopers and apparently I wasn’t alone.

According to Harvard Business Review, when sales and marketing executives were asked about the terms they use to describe each other, 87% of the responses were negative. Terms that sales used to describe marketing included, “paper pushers,” “academic,” and “irrelevant.”

Marketing described sales as, “simple minded,” “cowboys,” and “incompetent.” And we might as well add “party pooper” to that list.

It was a rift I couldn’t quite wrap my head around. How could two parts of a company that were routinely mentioned in the same sentence be so at odds with each other? How could they ever agree on what the goal was and how to accomplish it?

While the legendary marketing and sales rivalry may be older than the cold call, the real shocker is that it still exists to this day, to the detriment of business growth.

Not surprisingly the relationship between sales and marketing has a huge impact on a company’s revenue. According to the Aberdeen Group, companies whose sales and marketing teams are out of sync saw a 4% decrease in annual revenue, while those companies that found a way for everyone to be friends and play nicely together, saw a 20% bump in annual revenue.

So, needless to say, learning how to work a little United Nations diplomacy between your sales and marketing teams could significantly improve ROI, sales performance, and, most importantly, growth. And maybe even world peace, at least around the office.

Why Can’t We Be Friends?

Before we get into ideas for how to strengthen the relationship between the sales and marketing teams, let’s look at why there’s a problem in the first place.

Take my cousins as an example. Because they’re twins, everyone lumped them together as if they thought and acted the same way (they’re not even identical twins). They resented the fact that people didn’t recognize them as two individual boys with their own interests, skills, and ideas about the future.

Sales and marketing teams are like fraternal twins. If management doesn’t recognize them as distinct teams with different needs, it frustrates people within those departments and ultimately doesn’t produce the desired results.

Goals

The first area of difference is goals.

Sales teams are pushed to meet monthly, quarterly, and annual revenue goals - they’re watching the numbers.

Contrast that to marketing, which traditionally hasn’t been tied to revenue performance in the same way, and people on those teams are thinking more holistically, strategically.

Expectations of Roles

Sales and marketing teams often have a different understanding of what the other should be doing, and how they should be doing it for them.

Marketing thinks that the activity they generate produces leads that the sales team can then act on and try to close. But the sales team can’t always see how those activities are responsible for quality leads or revenue so they feel like they’re alone in doing all the work.

It can also seem to the marketing team that sales ignores all the content and support materials they produce for them, but the sales team thinks they’re not getting the right support or the right materials.

Each feels the other has the easier job, is carrying less responsibility for revenue, and hasn’t got a clue what their day-to-day challenges are.

No wonder there’s a problem.

So here are five suggestions on how to better align sales and marketing and get everyone focused on lead generation and revenue growth:

1. Align the Goals to ROI

Sales’ and marketing’s goals should be the same. They should be linked to ROI, period. They may each have different ways to create that return on investment and reach that goal, but it’s the only finishing line that counts.

This has been more challenging for marketing. Marketers have often had difficulty measuring their effectiveness in contributing directly to revenue, something agencies in particular have fallen short on in terms of client expectations.

By aligning everyone’s goal to ROI and finding ways to track that, like through KPIs (key performance indicators), everyone is going to feel more evenly paced and it should do away with any resentment around feeling like one department is carrying the entire load.

2. Attend Each Other’s Meetings

This was one of the strange things I found working at agencies when we’d get push back from the sales teams. Half the time we didn’t even know, or, admittedly, consider, that we were responsible for creating programs for sales, or think about how what we were doing could be translated into sales activity.

We rarely got to speak to sales directly, and our clients rarely brought them along to meetings (again, we were usually we dealing with the client’s internal marketing department).

So anything we were finding out about sales’ needs and challenges was after the fact, like sales just not implementing our strategy.

We tried to push back on this and started to insist that someone from sales be involved in the upfront discovery session so we could find out as much as we could in the beginning what sales needed to perform and what they were hearing at a customer level.

Then we could take those findings into consideration when developing our strategy or campaign, and provide guidance on how sales could apply it to their own benefit.

Working in silos is one of the most inefficient and damaging practices of any business. You need to understand how each department works, how what they do affects the company, and how it affects what you do.

Sales and marketing need to share information, not give or take orders from each other. By communicating better, each side can gain valuable intelligence that can help them be more effective in contributing to that ROI goal.

3. Focus on Your Sales Funnel

Sales and marketing usually have different ideas of what the stages of the sales funnel are, and what activities need to be completed to move a lead to the next level.

By defining the funnel together and agreeing on what happens at each stage, everyone knows what their role is and has more confidence about the kind of leads being produced and their ability to convert them.

While every business funnel may be slightly different, here’s a general example of the process:

4. Agree on Lead Generation

If marketing’s job is to generate leads that are handed off to sales to move further down the sales funnel toward a closed deal, there better be agreement on your definition of a Marketing Qualified Lead (MQL), Sales Accepted Lead (SAL), and a Sales Qualified Lead (SQL).

What often happens is the marketing team defines the MQL, which is generally a combination of characteristics (what industry they’re in, what level of decision maker they are), and behaviour (they’ve asked for a demo, they’ve engaged with your content) that add up to someone they think could be a potential customer.

The sales team outlines both what a SAL is — a lead that sales agrees has potential and will follow up with, and a SQL — a lead the sales team feels confident is going to convert into a customer.

If you’re not both in agreement about what makes a good lead, then there’s going to be disagreements about how marketing isn’t sending the right kind of leads that sales can actually close. Meanwhile marketing will accuse sales of squandering all the leads they send them by not closing enough deals.

So by defining and agreeing on the who, the what, and the when for the perfect timing to hand off to sales, the chances of successful follow through will increase significantly.

5. Collaborate on Great Content

Content’s role is to lure in potential leads and move them further down the funnel so it can be determined whether they’re a MQL or not.

It’s marketing’s job to create the content to support sales in this quest.That could be anything from blog posts and lead magnets, to product information sheets and proposals.

However, often times marketing decides what the content will be without much consultation with sales. Then they get upset when sales doesn’t use their materials or complains they’re not being supported properly.

To create great sticky content, marketing really needs to understand the customer and what their needs are, their objections, their questions. This shouldn’t be done based on assumptions, and there’s a valuable resource at the ready: the sales team. Since salespeople are the ones on the frontline, this is information they can provide to marketing to help inform the content.

Marketing and sales must to work together to define what the content needs are in every stage of the funnel, and ensure its customer-focused. This will make the entire process more efficient and effective.

We’re all on the same side

It is critical that sales and marketing teams lay down their egos, open the doors of communication, and remember that they’re all playing for the same team: the business.

By following these steps and changing thinking from one of adversarial competition to that of mutually beneficial collaboration, they’ll find it easier to do their jobs, their success rate will increase, and the business will prosper.

I was originally going to call this post “Stop asking to pick people’s brains”, or “How to make connections online without being a douche” but was advised against it.

In any case, we’ve all been there before, either on the receiving end of a new LinkedIn request asking to book a meeting, or maybe you’ve been the one doing the asking.

Social media allows us a chance to get in front of virtually everyone on the planet, if only for a fleeting moment. While technology for communication is evolving at an exponential rate, human beings are not. People still crave authentic connections.

As any recipient of a dick pic will inquire, why do so many still lack basic etiquette when reaching out to strangers online?

Consider this scenario, you’re sitting at the pub with a few friends when a stranger walks over with his eyes fixed on you.

Your immediate croc-brain response is “What does he want?”

Maybe he wants to ask what you ordered, or to compliment you on your new shorts? (Fact: I just bought new shorts)

Instead he says: “Hey, you look like a business person. Mind if I sit down with you and your friends to show you how I can help take your business to the next level?”

Now granted, most people would never do this in a pub, but they do it online every single day and then wonder why their response rate is so low.

Here’s just a sampling of the type of messages I get on a daily basis through LinkedIn (which I’m sure you get as well):

This is the equivalent of walking up to someone in a bar to make a sales pitch. It’s rude, it’s lazy, and gets ignored 100% of the time.

Why? Because it doesn’t offer me any value.

The one essential rule to effective cold outreach is value. 

It’s a simple concept on paper, but creating real value in practice takes a lot of work.

How to offer value when cold-emailing prospects

Let me first say that I hate doing outbound, direct sales. Maybe it’s because I grew up knocking on doors. Maybe it’s because I’m a bit introverted. Whatever, I hate it.

But sometimes it needs to be done.

The steps to succeed in cold-emailing are (in this order):

• Do your homework on the person/company before sending an email
• Stand out by personalizing the message
• Make a super easy ask

Do your homework before sending an email

There’s no point wasting your time or your sales lead’s if they aren’t the right fit. Send fewer cold outreach emails but make them more targeted, and more focused on their specific pain point.

Personalize your message

People are obsessed with themselves.

Researchers from Harvard used brain scanning technology and found that when people talk about themselves it triggers the same chemical reaction they experience during sex and this motivates them to share personal information more regularly. [read more]

Use this to your advantage. Don’t talk about YOU, talk about THEM.

What have they done recently?

Have they been featured in any news articles?

What do they seem to be struggling with?

After talking a bit about them, give a quick elevator pitch; Here’s what I do, why I do it, and how it can help.

Make a super easy ask

Don’t ask for a call right away. It’s too much of an ask if there’s no prior relationship. You can add your phone number in the email signature, but leave it up to them to ask for a call.

You want to make it ultra easy for them to complete your ask, such as “download this free guide” or “watch this 30 second video”. No pressure.

Using a tool like Yesware, Sidekick, or Proposify, you can know when someone opens your email and whether or not they click the link, then follow up from there if there’s interest.

With any luck, it will be as good or better than the best cold email I ever received.

Optional: Invite a lead to be a guest on your webinar/podcast

Kevin and I interviewed James Carbary on our podcast about this. He actually uses his podcast as a lead generation tool by reaching out to CEO’s and other high-falutin’ people he sells to.

Instead of asking them for a phone call, he invites them to be a guest on his podcast.

This does a few things:

• Provides free value - You’re helping get their message in front of your audience, which is free exposure for them.
• Strokes their ego - It’s flattering to be asked to be on someone else’s show and because it’s all about them it makes them feel valued and important.
• Builds the relationship - Through the course of planning the show, talking before and afterwards, you get to know each other a bit, so they feel a warm connection.

Then afterwards you can make your pitch. You may not close every deal, but 100% of people will allow you to pitch them.

How to offer value when approaching prospects for feedback/validation

Asking potential customers for feedback on a new idea is absolutely essential for entrepreneurs. Customer development is how businesses are built.

But how do you solicit feedback from people you don’t know?

Much like with sales, your email should address the pain you’re solving instead of focusing on you or your solution. Your attempt to solve a customer’s pain could translate into potential value for them, which may intrigue them to help you out.

Here’s a sample email I’ve put together you could use as a template for reaching out to perform customer/market research.

Ideally, it would be best to send this to your list of warm contacts first, but if you don’t have that yet it could still work as a cold email, just remember to personalize it.

“Hi [name],

I’m emailing you because I’m working on a new project, a product that’s meant to help [your industry] better [solve particular problem]

The basic problem I’m trying to solve is this:

[outline the full problem that person probably faces every day]

The idea I have aims to help you [do x, y and z to solve this problem].

It’s just an idea and a simple mockup at this point, but I want to make sure:

a) I’m solving a real problem that needs fixing

b) I’m not missing any key insight that could make the solution more valuable

Will you chat with me so that I can better understand if this is a problem for you, and how you currently solve it?

If so, please book a 15 min call at your convenience: [your link to Calendly]

I promise, I'm not selling you anything (yet!)

PS: At the end of the call I’ll show you the UI mockup for what I’m planning. It’s pretty cool :)

Notice how I’ve focused more on them and how I can help them instead of talking about my solution?

How to offer value when approaching people for advice/mentorship

What if you don’t want to sell anything — what if you just need help from someone more experienced than you? Maybe you follow a blogger you admire or some other “influencer” and want to get their advice or get in front of their audience.

The higher up the food chain you go, the more busy and thus unavailable people will be. That’s just a fact of life. It doesn’t mean Seth Godin isn’t a nice person, it just means he gets a lot of requests for help and likely has to say no most of the time in order to keep his sanity.

The quick route is to just pay for their consulting time. If you don’t have the cash to spend, or if he/she doesn’t accept consulting offers, then consider the following story:

How 2+ years of patience paid off

One of our board members is Ben Yoskovitz.

Ben’s pretty well known in the startup world, having founded and invested in multiple companies. He blogs, speaks at conferences, and is the co-author of Lean Analytics (published by O'Reilly), a book that was very helpful for me in growing Proposify.

I haven’t always known Ben.

The first time I heard of him, I was at a startup conference and Ben was giving a talk on Lean Analytics. I liked what he had to say, and learned a lot from his talk so I said hi to him afterwards to thank him and ask a few questions. I gave him a brief elevator pitch on what we did.

Ben’s a nice guy, but I could tell this was just another quick conversation of many he already had in a dimly-lit hotel lobby that day, and it probably wouldn’t stick in his memory.

In any case, after the conference I bought his book.

And read the book.

And emailed him to tell him how much I loved the book.

And I tweeted about how awesome the book was.

And then I suggested (or he suggested, I can’t remember) that I write a guest post on his site about how the book helped me. (Here’s the post in case you’re interested)

Over the course of the next two years I occasionally kept in touch with Ben, letting him know how we were doing, showing him our metrics, asking for small bits of advice here and there, and commenting on and sharing his blog posts.

At some point, we had grown quite a bit and needed a third-party board member, one who was neither an investor nor a co-founder. We wanted someone who would bring a lot of experience to the table.

So I sent Ben an email and just outright asked him if he’d like to chat about being on the board.

After a few phone calls he accepted our offer. Would that have happened if I cold emailed him, or asked him the first time we met? Probably not.

Takeaway: Nurture relationships over time, because when you do eventually need to make an ask you’ll have already laid the groundwork. Good things come to those who wait.

Bonus tip: How to earn money when people ask you for calls

Whether or not you consider them an “influencer”, every working professional is busy.

While I am flattered when people ask me for help with their business, being asked for a phone call by a stranger without being offered anything in return comes across as arrogant.

It’s not like I consider myself above anyone else or too important to talk to someone.

I’m a regular guy with a diploma in graphic design from community college. I’m divorced with two kids. The highlight of my weekend was buying discounted shorts from a Banana Republic outlet. (Yes, the same shorts that were complimented in my hypothetical story.)

But time is precious and a finite resource for anyone, and if you or I say yes to everybody who demands our time we may not have time to focus on the more important things; Our families, our friends, our business, our health, and our hobbies.

Not to mention that for some people, consulting is their actual job. You wouldn’t ask a massage therapist for “just a quick massage”, you’d book an appointment and pay for it.

I came across the article No, You Cannot Have “A Few Minutes” Of My Time recently where Hanna Brooks Olsen denounces those who ask for free advice online and how she handles it (basically by saying “Sure, I charge $150/hour”, and seeing what happens).

I think I have a better way though.

Clarity is an online marketplace for people who want business advice from experts.

When a stranger reaches out for advice I respond with:

“Hey Finnegan, thanks for reaching out. I’d be happy to chat with you to help you out, feel free to book a call here: https://clarity.fm/kyleracki”

The link goes to my Clarity profile, and Clarity makes it clear that booking a call costs money. They either book the call or they don’t.

At the end of the call, Clarity automatically charges the caller for the time, takes their cut and puts the rest in my PayPal account.

When I see that the person really does value my time, I don’t mind digging in ahead of the call to learn more about their business and try to offer them as much value in as little time as possible while we’re on the phone.

Often I’ll give them my direct contact info for future follow-up because they’ve proven they don’t just want something for nothing. They’ve put their money where their mouth is.

If you’re finding yourself getting a lot of phone call requests, give this approach a try and let me know how it works for you.

But the bottom line is, everyone’s time is worth something. Show that you respect it by offering them something of value in return. If you do, you’ll drastically improve your success rate.

Between my years in the agency world and then as a freelancer, I’ve been responsible for making sure a lot of projects stayed on the rails. Scope creep was an especially evil enemy, and the term usually evoked its own soundtrack in my head. You know that terrifying, urgent, knife-slashing violin music from Psycho?

I’m sure you’re more than familiar with the dreaded scope creep. It’s when features, or deliverables, or expectations slowly get added to a project without the budget or timeline being adjusted accordingly.

Project scope creep is like a leaky toilet. Each drop is not that big a deal on its own, but compounded over days, and weeks, and even months and you end up with, well, a shit show.

Poorly managed, scope creep can transform profitable projects into losses, damage client relationships, destroy timelines, and can be very hard on the morale and motivation of your team members.

And speaking from personal experience, dealing with scope creep after the fact is one of the biggest nightmares of managing a project. It’s like being stuck smack dab in the middle of an angry, pitchfork wielding mob.

Your job is to make the client happy, keep the project team focused, make sure the the project stays on time and on budget, and meet your own agency’s business goals. It’s an uneasy peace even the most experienced diplomat at the United Nations would find challenging to maintain.

That being said, controlling scope creep is probably the single most important responsibility of project management, whether that falls on you, or one of your team members.

So, how can you better manage scope creep and avoid the angry pitchfork mob chasing you out of town?

In short, by managing expectations, communicating clearly, and documenting everything like you were Harriet the freaking Spy.

Understand the client’s objectives

Before you start entering a single project milestone in Basecamp, you need to be very clear on what the client wants, needs, and expects to achieve out of this project.

A discovery session between the client and key members of your team is a good way to accomplish this - it’s like a fact-finding mission so you can gather all the intelligence you need about your client, their business, their challenges, and the results they’re looking for.

If you’re scoping a large project, it’s a good idea to begin by selling the client on a paid upfront discovery so you aren’t trying to define scope within a proposal when you don’t know what’s involved in the details.

This way you can take the proper time to plan any features or functionality, design interfaces, and if needed, create a rough prototype. Once everyone agrees on what you’re developing, you’ll be able to better estimate, and manage expectations.

Deeply understanding these parameters will help you develop the right deliverables for the project, the right budget, and the right timeline.

This will ensure your project scope fits the client’s expectations like a finely tailored suit. If it fits properly from the get go, they’re not going to come back a week later and ask you to hem the pants, move a button, or worse, change the fabric.

Break big projects into smaller projects

Small, bite-size chunks are safer to swallow and there’s less chance of choking.

It’s easier to define scope for small, straightforward projects but large ones can easily balloon because it’s just not possible to know what might emerge months down the road, the deeper you get into the weeds

Look at ways to break the project down into sprints, and plan and budget each of those as separate and distinct projects. Once you finish the first phase, it may inform changes or additions to the next phase and this gives you the latitude to adjust accordingly.

Involve your team in scoping out the project

Once you know what it is you’re going to do, you need to be sure you understand how it’s going to get done, and just as importantly, how long that’s going to take.

I tried to make a habit of consulting my project team members before finalizing deliverables, timeline, and budget. These are the people who are the experts in what they do and they’re the ones who are going to do the work so why wouldn’t I consult with them?

But it’s surprising how often project managers, salespeople, and other client-facing professionals make promises to clients and assumptions about projects without ever checking with the people who are actually going to execute the work.

“Oh sure, we can get that done in a week and it should only take about 25 hours,” could be the epitaph on many a project manager’s tombstone.

Through experience it does it get easier to estimate the requirements of a project but I still always wanted to double check with the designer, developer, or copywriter on my team because inevitably, the thing I thought was pretty straightforward that might take 25 hours of work, ended up having some some twist in it that required double that amount.

Or sometimes the project team had considerations or suggestions that wouldn’t have occurred to me. Things that could either complicate or simplify the project, but still things that needed to be addressed up front, not after the fact when it could be costly or messy to deal with.

Clearly define the project and responsibilities

Now that you understand what the client needs and what you’re going to deliver, you need to communicate all of that back to your client, and your team, in a way that leaves no ambiguity about what’s going to happen when, who’s responsible for doing it, how long it’s going to take, and how much it will cost.

You need to be explicit at this stage. It may seem like a pain in the butt, or that you’re being overzealous but later when you can refer back to that one point that saves your weary butt when the client complains that they expected four versions of a logo design when the budget clearly says it only includes two, you’ll be glad you were a little OCD.

And clients will appreciate this, too. If they feel they understand exactly what’s going to happen, it’s going to give them the confidence to trust your opinion, and they won’t try to micromanage you along the way.

There will be fewer annoying emails asking when something is going to be done, or angry phone calls wondering why something wasn’t done at all.

Another tip: go over all this information in person. Or at least by phone or Skype or something. Just don’t assume they read the document in detail and understand everything on their own. Go over it with them point by point so you know that they know. And they know you know they know.

Have a game plan for changes

Life is uncertain, imprecise, and fleeting. And so are clients.

Something may change once you’ve already started on the project so you need to be clear with the client what the plan of attack is for changes before anything actually happens.

Define how change requests get made, who is responsible for them, how it gets handled from a budget and timeline perspective, and what the implications are for the project overall.

Getting this all out in the open from the very beginning will help manage expectations and keep the project focused on its objectives. If a client fully understands the consequences of a change or addition on the timeline and budget, they’ll be less likely to make a cavalier request.

Get it signed

After you’ve gone over your very detailed project plan in person with your client and you’re certain they understand all the implications of how things are going to move forward, GET A SIGNATURE.

It’s standard to get a client to sign off when they accept a proposal, but it’s just as important to get their signature on the project plan. Otherwise, you are leaving yourself open to potential scope creep carnage down the road.

I admit, I wasn’t always vigilant on this. I naively assumed people were good on their word, and most of them are, but if they can find an escape route when they’re in a pinch, they’ll take it. And saying they didn’t understand something or weren’t aware of a particular condition so they can’t be held to accountable is the perfect scope creep escape route.

But if you’ve gone over the project plan with your client in person and had them sign off that they understand and agree, then you’re covered for how any changes will be handled.

Basecamp it, Baby!

I have been a Basecamp power user since 2007. When it was first introduced to me, I felt like a flock of project management angels floated down to save me from certain madness.

When I was working in an agency, Basecamp helped me manage every single aspect of a project, and allowed me to sleep at night.

Once a project plan was in place and signed off, I dumped it all into Basecamp - every task, milestone, timeline, additional resource, and then I invited everyone the project, both on the client and agency side, to participate.

This kept everything in one place - drafts, proofs, comments, sign-offs, change requests, final files - EVERYTHING.

Basecamp also helped me manage my own team, making it easier for them to know what was happening with the project and what their daily tasks and responsibilities were.

Whether you’re a Basecamp user (I swear they’re not paying me for this plug) or you prefer different project management software, the point is USE ONE.

There are lots of great tools out there to help you stay organized and communicate with your client and team. Tools like Trello, Zoho , or Podio. If there is a preventive measure against scope creep, this is one of them.

But again, even the best tool is useless if you’re not consistently using it. If anyone on my team ever sent me something about a project via email or asked me a question on chat, I would always refer them back to Basecamp. Everything, EVERYTHING, went through Basecamp.

At one agency I even had a sign on the door that said, “Basecamp it, bitches” and if someone wandered into my office asking me about a deadline for something or where a file was, I would just point at the sign.

And Basecamp, if you’re listening, I <3 you.

Watch your team

To be fair, you can’t place all the blame of scope creep on the client.

I have worked on a few projects where someone on the project team went rogue and totally overdelivered on something.

There was one art director I worked with in particular who was notorious for this. I almost had to stand over him at all times to make sure he was only doing what we were contracted to do.

He’d do things like, if a project was to redesign product packaging, he’d decide on his own that the client’s logo was ugly and then spend 20 hours designing new logos options. Without telling me.

Or, even though I had consulted with him in the proposal stage about how long a certain task would take, he’d end up spending three times as long on it, and not because of an issue that arose but just because he was enjoying what he was doing.

The thing is, if he had come to me BEFORE he went ahead and spent 20 extra hours on new logos options and explained why he felt it was necessary, I may have been able to go to the client and upsell them on a new aspect of the project.

But because it happened afterwards, there was little chance of recouping those costs, or the subsequent delay in the timeline.

We all want to deliver great service and quality to our clients but there is a fine line where over-delivery is actually costly scope creep.

Be sure your team is clocking their time in Harvest or some other time-tracking software so you can keep close watch before things things go over budget.

Stay in regular communication with your team members so you know the status of what they’re working on and how they’re doing time-wise.

Sometimes there are legitimate reasons for a project change but you want those to be opportunities for upselling, not scope creep, and the key to that is catching it BEFORE it happens.

Watch yourself

Not only do you need to keep an eye on your client and your team to prevent scope creep, you need to keep an eye on yourself.

You have to be vigilant about your own time, what you say yes or no to, whether it’s a request from the client or team, and how you enable scope creep. Remember, you’re the gatekeeper.

There are times when small, reasonable changes can be easily accommodated. Not all project change requests equal scope creep. But when requests comes in, you have to be very aware of which ones are going to have a minor impact on the budget or timeline, and which ones are going to lead to death and destruction.

And you need to be clear to the client the difference between those so you don’t create false expectations that you can accommodate changes every single time without consequence.

Acceptance is the first step

Well, in this case it’s the last, but the point is scope creep is always a threat, whether you like it or not.

There are a multitude of reasons why project change requests happen and not all of them are necessarily bad. Or they don’t have to be bad as long as you have a plan in place for dealing with them.

Planning for the threat of scope creep should be a natural part of your both your proposal and project development process. In the end, it will protect your business, the client, the project, and ultimately, your sanity.