Chief Introvert Officer
Starting and growing a company as an introvert
Much has been written about introverts and extroverts: the “Type A vs Type B” trope, most of it clickbait at best and pseudoscience at worst. How can our entire species be lumped into one of two groups, with no room for outliers or hybrids? Personally, sometimes I feel like the life of the party, while other times I’d rather be poked with hot needles than talk to other people.
I’m still speculative, but the process of starting a company, leading a team, and raising money does have a polarizing effect.
Starting Growbot, a bot for praise @ work, has taught me a lot about my own introverted tendencies. I’ve also learned that entrepreneurs who don’t thrive from social interaction will a) not do their job or b) quickly run out of steam. The trick (I’m learning) is figuring out when to use your introverted super powers and when to ignore them for the betterment of the company.
Talk the talk
Most of your time is spent talking. Talking with customers. Talking with co-founders. Talking with job candidates. Talking with investors. If you’re like me, just reading those words makes you want to curl up into a ball under your desk to recharge. I’m here to tell you that’s OK. While you can’t actually crawl under your desk every time you have to talk to somebody, it’s ok to have those feelings. In fact, you can even embrace them (at times). Guess what? You can have success* as an introverted CEO, small business owner, manager, etc.
*Success is super relative. I have no exits to my name, but I do have a product that people love and a team I’m proud of.
There were several early-stage hurdles particularly challenging for me. Trust me, I’m not saying these are easy for extroverts, either; plenty of my more social peers also struggle with these. But I made them harder on myself by not recognizing how my predisposition for social avoidance was holding me back.
Defining and communicating a vision
I’ve been working on Growbot for two years. In the early days I subscribed to “fake it ’til you make it.” Be the loud founder with an abiding fire for the problem I was solving and what I was building. Always selling. Always recruiting. Always pitching. Always ON|OFF. Guess what? I could only fake that energy for so long. My company and product evolved. After 6 months, doubt and exhaustion set in, and I started to feel like I was slinging a vision I didn’t fully understand. The emperor had no clothes. The imposter was exposed.
Your vision (and how well you communicate it) is the foundation of the startup house you’re building. It’s what will convince potential co-founders, investors, employees, and customers to make the irrational decision of joining you. With a product that’s not quite right in a market that is still being defined, it’s easy to get beat down or talked out of a vision by speaking with the wrong customers (late adopters) or VCs (follow-on investors), resulting in a vision that doesn’t resonate or is delivered with no panache. I’d leave most meetings with recurring thoughts of “he just didn’t get it” or “I can’t help that she doesn’t see this trend,” blaming others for their oversight or incompetence instead of my inability to communicate in a compelling way.
In the early days, a vision is not something you define once and then shout the loudest. A vision cannot be crafted in a vacuum. A vision is a mix of where you see the world in 2/5/10 years, how that connects with your product today, workshopping how the vision is communicated, and finding the right people to share that vision with. This process requires a lot of social interaction, but it’s worth it. Not only will your vision be 10x stronger, you’ll feel great about it. You are no longer an imposter. The energy required to excite other people will naturally flow through you, and as your company grows, your vision will grow more steadfast.
And what’s a low risk way to field test your vision…?
Interacting with customers
Product development is critical for startups. That’s obvious. But what drives that development? Intuition? Internal brainstorms? Ouija boards? Talking to customers is the best thing for any early stage startup. Learning what customers want or need (if you haven’t launched), what they like or don’t like (if they are using your product), or what they will pay for (disregard if you are Snapchat) is only possible if you seek it out.
[Introverted self] — “But I’m making the product better?! I don’t have time for customers.”
[Future self] — “You are an idiot. Pick up the phone.”
One thing most introverts are good at is listening. One of my skills is getting to the core of what people are saying and asking thoughtful questions to uncover new ideas, pains, features, etc. For that to happen a conversation has to actually take place. It’s far too easy for an introvert to put off customer calls and peck at the computer for 12 hours.
Push against your instinct to build build build. Take time each week to talk to customers. Email/chat is OK. Phone is better. In person is best. One caveat: it’s possible to go overboard with customer development. Spending all your time on the phone and no time building is problematic, but most founders are far from this side of the spectrum.
Fundraising
Many great articles have been written about how to fundraise and minimize the toll of never-ending emails, pitches, and rejection. This process is especially hard for first-time founders and introverts who aren’t clamoring to rub elbows with VCs or foaming at the mouth to attend happy hours, meetups, and pitch events. Unfortunately, there’s no magical solution to fundraising for introverts. It’s a grind. It will wear you down. I had to make a conscious effort to do things I normally wouldn’t (networking events, etc). The only thing that kept me going was my co-founders, my customers, and the thought that if I fail then Growbot might die.
Team Process
As an introverted leader, it’s very tempting to assume your small team will always be in sync. Ineffective communication is at the root of most failures (96% according to Salesforce). The smaller the team, the more important it is for everyone to work towards a common goal. The only way to ensure that happens is process and communication.
“The single biggest problem in communication is the illusion that it has taken place.” — George Shaw
It’s very important to establish and stick to a process of staying in sync (this includes day-to-day and Big Picture). Find a cadence that works for you and resist the urge to move or delete meetings. It’s important for collaboration and morale to get in a room and remind everyone what you’re working on and why.
Team conflict
Hopefully you’ve assembled a team of passionate individuals willing to fight for what they believe in. This passion often leads to debates or flat-out disagreements related to product, strategy, priorities, pricing, etc. The list of potential conflicts are endless and happen at companies of all sizes. If not addressed properly, these disagreements can fester.
As an introvert, it’s very tempting to sweep these disputes under the rug. It might feel good now to ignore that cultural rash, but in 6 months that rash has spread and you’ll have to amputate the leg. Lead by example and openly address conflict or disagreement.
Suck it up
One could summarize these learnings as “suck it up you introverted nerd. Go talk to people.” While that is a (harsh) oversimplification, it’s kind of true.
Knowing this, it’s important to find a sustainable routine that allows you to recharge. These have worked wonders for me:
- Don’t stop iterating on your story until you can’t stop talking about it — It was so easy for me to talk about sports or Game of Thrones for hours. I needed to find a way to talk about my business with the same passion as my latest Netflix obsession. This can’t happen until you find the right problem to solve or the right way to talk about it.
- Start the day by creating (selfish) energy — I get my head on straight with a workout. It’s the first thing I do. The endorphins from a run or lift fuel me through a day of necessary social interaction. Find what gives you the most energy and prioritize it.
- Space out the meetings — I don’t schedule meetings until 10am, and I try to give myself at least an hour between meetings to do work or think about hard problems.
- Occasional solo lunch — It’s important to deepen relationships with co-workers, but sometimes I need to eat alone and catch up on Hacker News or a favorite podcast. Be careful not to form a habit around this, but use it when you need it.
- Get outside — I walk to and from work. For those with a less fortunate commute, find ways to get outside a few times a day. Schedule walking meetings, take a 2pm break, etc. The combination of being outside + light physical activity is a surefire energy boost.
- Delegate — As CEO, it’s very easy to adopt a “I can do it all” mentality. Not only does this give people the impression that they aren’t trusted, it fills your day with work or meetings you shouldn’t be doing. This sucks up much needed energy from other areas. Find the right people to help you and trust them to do great work.
- Turn off @ 10pm — Sleep is so important. I get at least 7 hours a night. It’s also important to have a great routine leading up to bed so I can fall asleep quickly and sleep heavily. This meant turning off the computer, TV, and phone a few hours before bed.
I’m excited to continue this journey, even if some days I just feel like building and hiding inside a fort.
It’s hard for an introvert like to me to ask, but if you liked this piece please follow & share.
