The Experience of Being a CEO
What startup CEOs told me about the role
CEOs are a particular kind of leader. While running businesses are a team effort, in my experience, the CEO takes on the most responsibility. Through my work as a leadership consultant I’ve been lucky to spend time with many CEOs. I’ve interviewed five CEOs for the leader conversation series:
Beth Smith: Being Open and Vulnerable as a CEO
David Jarvis: Being a First Time CEO at a Startup in a Highly Regulated Industry
Lilly Chen: Being an Accidental Startup CEO
Zac Smith: Leading a Company Through Acquisition (joint interview with Zac’s twin brother Jacob, a co-founder of Packet)
Henrik Mattson: Being a Startup CEO as a Non-Founder
Since these conversations are mixed in with other content, I thought it might be nice to pull some themes into one edition. Click to read the full interview of each.
Being CEO wasn’t a goal
“If someone had told me I'd be COO of a thriving business, a number of years ago, I'd have been like, "Really what?" And if they'd said, "You'll be CEO," I would have been even more sort of like, puppy, dog head turned sideways, like, "Really?" I think it's about following breadcrumbs and paths that are laid out.”
“Taking both those roles were pretty big risks - around the not knowing. Truth is, I didn't really have the traditional qualifications on paper, what might look like all the talent needed, but certainly it all worked out.”
For Lilly Chen, a former monk, the role came accidentally after she and her friends built a product out of boredom.
“I have more industry experience because I'm older and I kind of jumped right in...they kind of just decided they were like, it makes the most sense for you to be the CEO.”
“I have actually tried to give it up (being CEO) in the past. There was one time when I said like, "UN-ironically, would any of you be interested in a little swippy swap? You know like that show Wife Swap, a job swap. Would any of you be interested? I really miss coding.” They were like, "Ooh, we don't want none of that."
Henrik Mattson, CEO of Lookback who started his career with a Ph.D. in economic geography didn’t expect to be CEO. When the startup he worked for started to run out of money he met with the founders to discuss what to do.
"During those meetings, I had some very strong opinions, I guess, about what would work, and more importantly, what wouldn't work. It was very clear to me that what we had been doing, wasn't working. I was like, "Look, this is serious. If we get this one wrong now, we're going to run out of cash in three months, and then it's over." At one point, my predecessor (the CEO at the time) said, "Oh, perhaps Henrik should be CEO," and then one of the other co-founders said, "Yeah, perhaps he should," and they kicked me out of the room to talk.
I went for a walk. One hour later, they called me back in and gave me the mandate, so that was a bit of a shock.”
(at a previous job) “The CTO was like, "Well, what do you want to do? Where do you want this to go?" I was like, "I think I want what Matt has." He was like, "I don't think so." He's like, "I think you're a CEO. I think that's what you're going to be." And I was like, "Okay. Vote of confidence, I guess." (chuckles) But I think that was the first person who really felt that that was the place where I was going to end up.”
“If I was looking to hire my replacement and someone showed up with my other leadership roles, as the only things on their CV, I would be like, "This is a joke, right?” These are sandbox leadership roles, but that doesn't mean that there weren't really valuable lessons in them. In some ways, sandbox leadership is a good and safer way of letting someone grow than putting them straight in the fire.”
What’s hardest about the role
“(Hiring) is really challenging, especially if you are a first-time founder. Even if you’re not a first-time founder, if you're doing anything in an area that you're somewhat new to, you have to hire people in a discipline that you yourself are incompetent in, probably, right? And you have to do that like 10 times as the company grows.”
“Realizing that I didn't know very much about myself. I thought I did. You always want to think that, right? You always want to think that I know who I am. I know what I want in life. But no, I think early on, I was solving immediate problems…I always try to solve other people's problems, but what am I looking for? Realizing what my motivations are, what gives me energy?”
Zac Smith on leading the company while going through an acquisition:
“This is the interesting part about being in the middle of a potential M&A process. You do all the work before anything is finalized. Anything can go wrong at the end and just fall apart. There’s a lot of negotiation that happens at the 11th hour. You're highly invested. You've spent a ton of time, a ton of money, right, to go through some sort of potential M&A. But when you're working with a public company, in particular, you can't share this information with your team.
So you're working internally, maybe CEO, CFO, a few key people who are all moonlighting this work. And at the same time, you're often at a very important phase of your business. So you're growing. You're doing all this kind of stuff. So you're playing already burning the candle at two ends as a startup founder, but now you're doing another job called engaging an entire M&A process.”
“When you become CEO you can't optimize for things like your career. You have to take risks knowing that if you mess up, you'll be fired. That's the job.”
Advice to their pre-CEO self
“I think you have to have a lot of good business acumen to be in a role like COO or CEO. But I almost feel like, with every passing day, you have to understand the human condition too. Because it's the compliment of how you're using business acumen and tried and true business philosophies and frameworks to help a company move forward. But it's the people that are doing all that. So having leadership and mindful awareness skillsets, I think, it's more critical now than ever. And it has a lot to do with empathy too. And being able to be compassionate and empathetic, all while at the same time holding people accountable to a role that they've accepted and that we need them to do really well in to help the company continue to thrive. So there's this balancing act.”
“Think about what kind of person you want to be. In a worst-case situation, if everything goes to crap, what do you want to get out of this? What kind of person do you want to be at the end of this? There are many, many ways to lead a team, to lead a company, but think a lot about who you are and what you want to get out of it.”
One of the things that we both prioritize (of his co-founder and twin brother) that is so important to our business, which was around the culture. Yet, we had no senior leadership who represented that. If I would go back in time, back in 2014 or 2015, I would've hired a people leader from the beginning instead of in 2019, which is when we finally got somebody to actually take that as their stewardship.
So for me, it would've been about that because I could see how we would've been applying our values more purposely. How we would've handled performance management. How we would've helped have the right people together in teams that would've meaningfully changed our trajectory and outcomes.
“Be kind. This is hard. Be kind to yourself, and be kind to others.”
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