On Failure and Leadership

I have a failure story I still think about (and sometimes, honestly, still cringe over...), years later, and it's not the one people expect. It's not a product that flopped or a funding round that fell through (though, truth be told, I have plenty of those failures). This failure is about a hiring mistake.

At Reaction Commerce, in the early days, I hired a Chief Operating Officer. On paper it made sense. The board was asking about our sales motion. Growth needed a name and a face and a plan, and I was a first-time CEO who wanted to look like I had this handled. So I went and found a great one. Genuinely great. Someone with a real track record, someone who could walk into a boardroom and speak fluent enterprise sales.

The problem wasn't the person. The problem was the timing, and underneath the timing, the problem was me.

We weren't ready for a COO. We didn't have a playbook yet. We didn't know, in our bones, why customers said yes or why they said no, what objections actually killed a deal versus which ones were just noise. That knowledge doesn't live in a deck or a CRM. It lives in the founder, earned conversation by conversation, until you can feel the shape of it. I hadn't done that work yet. Our product wasn't ready. I had skipped the part where I was supposed to be in every sales call, taking the losses personally, building the muscle myself before I handed it to someone else.

Instead I hired someone to do the thing I hadn't yet learned to do.

It didn't work. It couldn't have worked, not because they weren't capable, but because there was no playbook to hand to them. Eventually we had to let them go. It was hard on them and it was hard on me, and I remember sitting with the fact that I had seen it coming, some quiet version of me had known it was too early, and I overrode that instinct anyway because the board wanted a story about scale and I wanted to give them one.

That's the part I keep coming back to. Not the mistake itself. The moment right before it, when I knew and talked myself out of knowing.

Sitting with a founder in the same spot

I was recently coaching an early-stage founder who came from a big corporate background before starting their own thing. We ended up talking about failure and leadership, in the way these conversations tend to sneak up on you, starting as a question about a hiring decision, or a contract decision, and ending up somewhere much more personal.

What struck me was how much of their relationship to failure had been formed somewhere else, at some other company, earlier in their life, under some other set of incentives, long before they ever founded anything. They'd learned to manage the appearance of failure. Get ahead of it, control the story, keep it from touching them directly, because in a big company your career can survive almost anything if you handle the narrative well enough. That instinct served them for fifteen years. Now it was working against them, because a startup doesn't have room for a founder who's managing perception instead of sitting in the actual problem. There's also a delicate balance of sharing with your team and oversharing with your team, while navigating the ups and downs of a situation.

I recognized the pattern immediately, because it was mine too, just wearing a different costume. Theirs was corporate polish and potentially oversharing. Mine was a board that wanted proof I could scale. Different pressure, same result: overriding what I actually knew to be true in favor of what looked responsible.

We talked through a distinction I go back to often, from Amy Edmondson's research on failure. She separates failures into three kinds. Basic failures, which are the plain mistakes, the ones you could have avoided with more care or more process, nothing complicated about them. Complex failures, where a handful of things go wrong at once and no single cause explains it. And intelligent failures, which are the ones that happen when you make a real, thoughtful attempt at something genuinely uncertain, and it doesn't work out anyway.

My COO hire doesn't fit neatly into any one box, and that's probably the point. Some of it was a basic failure. I ignored a signal I already had. But some of it was an intelligent failure too. I was making a real bet, informed by real information, in territory that was genuinely new to me. I'd never scaled a sales org before. I didn't know yet what I didn't know. The distinction matters because I spent a long time treating the whole thing as pure basic failure, pure carelessness, when really some of it was the honest cost of doing something for the first time.

That's usually where the shame lives, in the blur between the two. You did something careless and you did something brave, and instead of separating them out, you let the careless part color the whole story so you can't see the brave part at all.

What actually changes things

Ed Catmull wrote something in Creativity, Inc. that I think about constantly, which is that failure isn't some unfortunate cost of doing original work, it's a direct consequence of it. If you're not failing, you're probably not doing anything new. I like that framing because it removes the moral weight from failure and puts it back where it belongs, on the size of the swing, not the size of the person swinging.

And there's a story I love about Sara Blakely, founder of Spanx, whose father used to ask her and her brother at dinner what they'd failed at that week, and he'd celebrate the answer, not tolerate it, celebrate it. I think about how different my relationship to that COO decision might have been if I'd had a version of that question running in the back of my mind at the time. Not "how do I avoid ever having to explain this to the board," but "what did I actually learn by trying."

The thing I told the founder I was coaching, and the thing I still have to tell myself, is that how you fail in front of your team becomes the template for how they fail in front of you. If I white knuckle it, if I get defensive or quietly ashamed, that's the permission structure I'm handing everyone under me. If I can talk about the COO hire the way I'm talking about it here, plainly, without pretending it was either nothing or everything, that's a different kind of permission.

I don't think I fully believed that yet when it happened. I believe it now, mostly because I've had the years since to look at it without flinching. The letting go of our COO and the letting go of my own need to look like I had it handled from day one, those happened together, and I'm not sure I could have done one without the other.