I didn’t set out to lead a company. In fact, nothing could have been further from my plan. I was a struggling artist with a BFA in painting, living and working in Cleveland, Ohio, in the mid-90s. Then I heard about these magical things called personal computers, and software, and scanners, and the internet. My world changed forever the moment I purchased my first Mac.
Creating a company, growing that company, and helping it turn into a great company — that has to be a deliberate process at some point. This “thing” you are building entails much more than profits, foosball tables and fun happy hours.
The people are what make the company. You are not building a “company” you are building people, just as you continue to build yourself. When you realize this, it completely changes how you think about your role as a leader.
Here are 13 things I’ve learned over the course of leading my company, and I hope you find them helpful.
1. Expect the stress and messy people stuff.
We are essentially a bunch of people working for other people Our clients are people working for other people, too. People are sensitive, chaotic, ever-changing, and complex. Working together is a recipe for loads of drama.
People are messy. People make things dramatic.
There will never NOT be stress and drama in a world with people, so you better get good at people stuff. Successfully dealing with your people is the most important thing you can do as a leader.
2. Hire people you like.
This one is easy. We spend more waking time with our coworkers than we do with our families, our friends, or our local bartender. We spend a lot of god-damned time with each other, and if we don't like each other it’s just torture.
Don’t try to talk yourself into liking someone.
If you interview someone and they seem like an asshole, they’re an asshole. If a cover letter reeks of ego, they’re an egomaniac. If they are weird when they come in to meet the team, they’re weird.
You will invite cancer into your company if you invite in people you don’t like, or that your team doesn’t like. Friendship and trust take time, but, it is just not possible to make an unlikeable person likable.
Never underestimate the importance of emotional health and well-being to a company’s success, and ensuring you let the right ones in.
3. Be kind and expect others to be kind.
Kindness seems to be a forgotten asset in business. Being kind to others is important. Being mean or cruel does nothing to build a team. Kindness lets someone know they can trust you, and that it’s ok for them to not be perfect all the time. (This is good because nobody’s perfect all the time.)
So be kind, please. Life is short and will provide its own built in forms of cruelty and sadness, so there’s no need for anyone to add extra cruelty into the world.
Kindness lets others know they can be honest with you and with each other.
Kindness lets others know they can disagree with you without getting their head bitten off, kindness invites input, and if you want to grow, you need the input of your team.
4. Learn what you don’t like.
Face it, you’re going to have bad days. Shitty things will happen, you will curse and you will cry and you will swear you are going to have a heart attack. But it’s ok to fail. In fact, sometimes it’s the best thing you can do.
You will likely take those lessons with you for years. I worked at a company for six months before I started Fastspot, and it was the most horrible experience of my life. I learned more from that period of my life than any MBA could have taught me.
I’ve learned what I hated, what felt like total shit, what was not tolerable. I learned what ugly and horrid managers looked like. I learned what cheating and manipulation was all about. I learned about what didn’t feel “human” about business, and that set the foundation for my future.
Sometimes knowing what you don't like is more helpful than knowing what you do like.
5. Don't go insane.
For real. Don’t go crazy. That won’t do anyone any good. It’s just web work. It’s just a site, or a deliverable, or whatever. I mean if you’re an actual brain surgeon or some other kind of person whose hands may cause death with an ill-timed tremble, I’m sorry. That’s stressful stuff.
Generally, what we are all doing at work — it’s not life or death for the most part. So save the going crazy behavior for when life really delivers a gut punch, it’ll happen, and you can unleash the insanity or the sadness or the freak-out at that point.
At work, especially if you're in a leadership position, keep your shit together. If you don't, you'll definitely lose a ton of credibility.
People are looking to you for how to behave, so don't end up with a whole company of people who thinks it’s ok to go bat-shit crazy every time things get a little bit stressful.
6. Keep it in perspective.
Remember, when real-life awful shit does happen, be sensitive to those going through it. We have an unspoken rule at work that when someone experiences something really hard (the serious illness of a child, the death of a loved one, a personal illness or problem) — everything gets pulled off their plate, and the team picks up the slack so they can deal with whatever is happening.
In our contracts we refer to it as “Force Majeure” and it’s in there for a very important reason. Work can wait, life will not.
7. Say “Thank You.”
Say it all the time. Don't expect others to say it to you. It’s your job to think about it for your team, and to show them that saying it to each other is critical.
Celebrate “thank yous.” Build “thank yous” into your culture. Give a Friday shout out to someone at your company every week, or let the team all vote on why someone should get the shout out.
Give praise, often, and whenever it’s deserved. Say thank you to people who do the hard thing, or the unglamorous thing, or the selfless thing. Say thank you to the person at the bottom of the ladder, who gets the least attention.
Give that praise publicly if possible. Being thanked in front of everyone feels really good.
8. Vacation and “Time Off” are your best allies.
Learn how to turn work off. This doesn't mean stop loving it, just get a break from it.
Leaving your normal routine (home, office, etc.) makes it much harder to let the routine govern you, and opens your mind up to creative thinking — which you’ll always need more time for.
So work those breaks in, develop patterns and habits that give you the breaks, and truly check out. For some it is exercise, meditation, medication (kidding), travel, time with family, reading, gardening, painting, biking, and the list goes on.
You’ll come up with better solutions and be more available for your team if you give yourself necessary breaks and reprieves. There’s even some science around the concept of travel equating to more creativity. And don’t worry, you won’t forget about all the shit that was driving you crazy at the office. It will be there waiting for you Monday morning, or when you get back from your vacation.
9. Celebrate every victory, learn from every defeat.
After a time, the big waves feel more like small swells. The dark corners are a bit more illuminated. The OMG things aren’t OMG any more, they’re just the things you have to deal with as part doing your job. That doesn’t mean they are less huge or important or impactful in how they will shape your future.
The victories and defeats still have good lessons to yield, and while they may feel more familiar to you, there’s probably someone sitting near by who’s never experienced that feeling of success (or failure) before. Let those around you know it matters.
Don't let victories ever feel expected. And don’t think failures have nothing to do with you or your team.
If you ignore them, you're likely doomed (or blessed) to repeat them. But you'll never be able to learn from them if you don't study them.
10. Be a good listener and keep your BS detector on high.
Sometimes the best thing is to be a good listener.
We recently did a “Peaks and Valleys” exercise at our retreat and it was amazing. We went around the circle and everyone shared a high point and a low point in their lives — it could be personal, work related, deep or just something recent. The point was to share with each other, and get to know something we didn’t know about each other.
Sharing a low and high point in your life with people you don’t know that well can be scary, and it requires everyone to be vulnerable. Bullshit (sarcasm, passive aggressiveness, backstabbing, eye rolling, undermining actions) is toxic to a team, and should never be allowed to exist. If someone is bullshitting the team, it’s your job to call them out, or create an environment where your team can call them out.
Creating safe spaces and time for this to happen is critical to a team of people becoming successful.
Remember that it’s your job to keep things real. Keep the conversation honest, open, kind, and generous.
11. Ask for help when you need help.
A wise friend once told me, “There are probably a lot of people out there who would be willing to help you if you needed it, but they will never know if you don’t ask for it.”
There will be times when you need help.
Sometimes you’ll also need help from your team. Let them help you. Be specific about what you need and how they can help you, and then allow them to.
Sometimes you’ll need the help of outside counsel, perspective from someone who can see things more clearly, or has different experiences to pull from. This may be a trusted friend, a counselor, a coach or a fellow business leader.
Ask as soon as you think you feel the need for some help, and don’t foolishly think you have to do everything by yourself.
We’ve been very fortunate to work with Jen Dary from Be Plucky. Jen offers me great advice and a thoughtful ear when I need it, and she also listens to our team and keeps her finger on their pulse as we plow ahead. I kind of consider her our company therapist, and I highly recommend you have one of your own to provide that kind of help on a regular basis.
12. Find the soul of your company.
It sounds cheesy, corny, hokey — and it kind of feels that way — but if you can think about your company as an entity, a being that has hopes and dreams and values and emotions, you will allow your company to thrive.
You owe it to yourself, your colleagues, your employees, your clients, and your company — to have a heart to heart. It might happen during the first week of starting your company, it might take 12 years.
This “heart-to-heart” involves you asking yourself what your deepest, most aspirational goals are for your company. If your company could achieve anything, satisfy any longing, perform any miracle — what might that be? Dig deep, and don’t be afraid to dream big. Dreams aren’t necessarily about achieving “the dream.” They are about having something always slightly out of reach. This will keep you getting up in the morning, and going to work.
I’ve realized my dreams for my company have mostly to do with what we can achieve as humans working together as a team.
13. Let Go
Letting go of your hold on the company and the need for “you” to be the key ingredient will make room for something new.
Your company, at some point, needs to live and breath on its own. It can’t do that if it’s always tied intrinsically to you, the creator. Just like a parent, you need give it the life and strength it needs, and then let it grow up.
The creation that happens in the place you made room for, it will be amazing. So give it space, breathe some life into it, and let it live.
If you enjoyed this post, I’d be super happy if you’d recommend or share it. I also welcome comments and thoughts.Thank you for reading it!
Most of the lovely photos in this post were shot by the very talented Yianni Mathioudakis.