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Lessons Learned

How I Knew It Was Time To Fire Myself As My Startup's CEO

CEOs are expected to recognize when somebody is no longer the right fit for a job. But what if it's you?

How I Knew It Was Time To Fire Myself As My Startup's CEO

[Photo: timscottrom/iStock]

By now, I’ve learned to start my firing conversations the same way every time: "There’s no easy way to say this, so let’s just get at it. At this stage in the company’s growth, you’re not the right person for the job you’re in."

And then, bang—they’re gone. Not because I’m a heartless jackass, though. For me, it’s usually because I’ve spent six months to a year wrestling with the sick, sinking feeling that the colleague in question really isn’t the right person for the job they’re in, and it’s holding the company back.

But it was a different sort of wrestling match when the "colleague" in question was me. I stepped down as CEO of my startup just last week, but I'd been having that conversation with myself for a long while before then, and it wasn't much easier in my head than it was sitting across from one of my employees.

Chief Executive Underachiever

After a year spent bootstrapping my company, then three years of chiseling away at a giant-but-ill-defined Mount Rushmore of market need, we were succeeding. We'd discovered the clear outlines of a monumental opportunity and our elegant solution to it. We had also reached honest-to-goodness profitability. After all the skepticism, all the stress, all the struggle, the company just needed to execute, execute, execute.

But as operational year No. 4 wore on, that familiar "this isn’t the right person" dread began to creep back in. It started as the barest whiff of risk aversion. A nagging sense that things were going well but falling materially short of what felt possible. A slight sensation of helplessness when it came to solving stubborn, recurring problems. Gut-level founder stress.

I always say I’m really good at connecting dots. When I connected these, the picture that emerged looked an awful lot like underachievement. And I was the chief executive underachiever.

That thought entered my brain and amplified as the months went by. But what to do? Did my senior team recognize it, too? If they didn’t but I did, and I fessed up to it, wouldn’t that shatter their confidence in the flightworthiness of the structure we'd built together? And even if they believed enough in what we were doing to keep the faith, how in the world was I going to find a replacement—especially when I wasn’t sure I knew exactly what a replacement should look like?

I spent a solid six months wrangling that sick, sinking feeling. "Not the right person for the job they’re in": My own words, running on a hissing tape loop in my brain.

I finally reached the conclusion that the company I had worked so hard and so long to build—now better positioned to succeed than I could've imagined at the outset—was in danger of missing its window. Not because anyone had caught us or rivaled us, but because I didn’t have the skill set for that "execute, execute, execute" thing. Not at scale. Not in an orderly, systematic way.

I’d love to tell you I knew exactly what to do next. We weren’t cash-flush enough to undergo a big-time search, and I didn’t want to raise capital on the false pretense that I was the leader to march us down the road we were building. I felt like Batman in the old TV series, stuck and calmly sinking in quicksand.

What You Learn When You Fire Yourself

But as the saying goes, "Cometh the hour, cometh the man." With the humility that set in after the anxious suspicion that I wasn’t the person the company needed now came an unexpected watchfulness: Suddenly, and almost involuntarily, my eyes and brain began to look around for what (and who) the company would need without me helming it.

So when I heard that a noted tech CEO friend of mine was looking for his next mountain to climb, I sent him a text (on October 18, 2016, to be exact) and boldly asked him if he’d consider talking to me about taking over my company as CEO. Before he could even respond, I sent him two more:

I’m incredibly proud of what we’ve created & genuinely believe our company can change (our industry). But I’ve concluded that’s a whole lot more likely with a real CEO driving it.

Worth a coffee?

He did his homework on us, and we did a heroic amount of work together to make sure of the fit going forward. Just shy of four months later, he officially came aboard, and I disembarked.

Well, not entirely. I’m still here, after all. Realizing that I wasn't the CEO my startup needs most right now helped me reassess my own strengths. And the process of stepping aside and hiring my replacement taught me something valuable about what I know I can do well: I’m a pretty capable salesman, strategist, and evangelist, and I'm going to keep focusing on those strengths. Plus, I’m still the company’s biggest shareholder.

Sometimes you need to fire yourself from a project that you can tell will succeed better without you in order to know what you're really cut out for. Right now, I feel engaged and energized, and incredibly relieved.

They say when you reach the conclusion that a team member’s got to go, you’re rarely wrong, and you’re doing both the company and the individual a favor by taking the action.

Even when it’s you.


Dave Maney is the founder and chairman of Deke Digital, LLC and two companies before. He is a father of six and a frequent commentator on the information-flooded economic revolution we're all living through.

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