Mission: Impossible

Here's a pattern I've seen play out at multiple companies, and lived through twice myself: A startup hires a senior product leader. Six to twelve months later, that person is gone. The internal narrative is some version of "it didn't work out". Maybe they weren’t experienced enough, maybe they weren't a culture fit, maybe they just couldn't hack it at this stage. The company goes back to market, finds someone new, and the cycle repeats. Everyone treats each failure as an isolated hiring mistake rather than a symptom of something structural. And the new hire, flattered to be chosen, never thinks to ask why the last person failed, or whether they're walking into the same impossible situation.

I want to talk about what's actually happening here, because I don't think most companies are honest with themselves about it. The problem usually isn't the person. The problem is that the company has created conditions where no one could succeed, and then blames the individual when they don't.

The Setup

At one startup, I was the PM leader brought in after my predecessor was let go. The CTO I reported to was openly dismissive of the previous person: described him as arrogant, said he hadn't delivered anything in his six to nine months there. I'd actually been up for the same job when they hired him, someone with ten to fifteen more years of experience and a much fancier resume than mine. So there was a part of me that felt vindicated hearing he hadn't worked out. Maybe I should have gotten the job the first time around. Maybe they'd finally realized they needed someone like me.

That feeling, being chosen after someone else failed, is seductive. It makes you feel special. It also made me incurious about what actually happened. I didn't push hard on why my predecessor had struggled. I didn't try to talk to him, even though the thought occurred to me. I'd drunk the Kool-Aid that he was a jerk who couldn't deliver, and I was eager to prove I was different.

What I discovered over the following months was a different picture entirely. I inherited a team of PMs who were extremely junior relative to their Senior titles, none of whom had any real role clarity or sense of ownership. The company's processes and documentation were chaos. And from a technical perspective, the CTO prided himself on having built something so complex that, in his words, "no one person can explain all of it to you." So all that "unproductive" time my predecessor had spent? In retrospect, it was probably the foundational alignment, documentation, and training work that would have been necessary to build anything on top of a shaky platform. He was probably doing the job. It just wasn't visible or valued.

The Accountability Shell Game

Here's the thing that took me too long to understand: when my boss acknowledged that the previous hire hadn't worked out, it didn’t mean anything would be different for me. "I made a bad hire. I shouldn't have brought that person in. I'll do better next time." On the surface, this sounds like accountability. But listen to what's actually being said. The accountability is for the selection, not for the environment, the support, or the setup. "I hired wrong" requires no change to how the company operates. It just means being more careful next time about who you pick. "I failed to support this person" or "I created conditions where they couldn't succeed" would require actually changing something.

This is the shell game that lets the cycle repeat. The company never has to examine whether it built an impossible job. It just has to find someone new to fill it. And because each new hire arrives feeling chosen, feeling like they will be the one to succeed where others failed, they often don't ask the hard questions. They don't talk to their predecessor. They don't probe on what will be different this time. They take the job, inherit the same broken situation, and eighteen months later they're the one being described as "not a fit."

The Asymmetry Nobody Talks About

There's another dynamic underneath this that I've seen repeatedly but rarely heard anyone name. When a founder or CEO hires a “technical” role, for example a CTO, they understand they're bringing in expertise they don't have. They can't write code. They don't know how to architect systems. They recognize that engineering requires specialized knowledge, and they defer to it accordingly. But when they hire a senior product leader, something different happens. Many founders don't believe product leadership requires specialized skills they lack. After all, they've been "doing product" since day one. They have opinions about what to build. They understand the customer. They have conviction. So what exactly is this product person going to do that they couldn't do themselves?

This asymmetry creates an impossible dynamic. The product hire is expected to add value, but there's no acknowledged domain where the founder will defer to their judgment. If the product leader reaches different conclusions than the founder, it's not read as "they have a different valid perspective based on their expertise." It's read as "they don't understand what we're doing here" or "they're not bought in."

What Actually Happened to Your Last Product Hire

If you're a founder or CEO who's been through one or more failed senior product hires, I'd invite you to consider an alternative explanation to "we hired wrong." Consider that you may have built a job that nobody could succeed in. Not because the job is inherently impossible, but because the conditions for success were never adequately created. The tell is in how you talk about what happened. If your explanation focuses entirely on the individual — their attitude, their approach, their gaps — you haven't examined your own contribution. If you "took accountability" by saying you'd hire better next time, but changed nothing about how you support, empower, or set up product leaders to succeed, you've just reloaded the trap for the next person.

Here are some questions worth sitting with: When your last product hire asked for resources, support, or organizational changes, how did you respond? Did you help remove obstacles, or did you tell them to make it work with what they had? Did you actually let them make decisions, or did you require everything to route through you? When they reached conclusions that differed from yours, did you engage with their reasoning, or did you override them? Did you give them a team that could execute, or did they inherit a mess and get blamed when they couldn't deliver miracles? Did you ensure they had access to the context and documentation needed to get up to speed, or did they spend their first six months just trying to understand what was going on? And finally, did you ever ask your previous product hire what actually happened? Or did you take their departure as confirmation that they weren't right for the role, and move on without looking back?

Call Your Predecessor

If you're a product leader considering a role at a company that's been through one or more failed hires at your level, I want to offer a piece of advice I wish I'd followed myself: talk to your predecessor. Not a casual "I should probably do this" thought that you never follow up on. Actually do it. The company has a story about why that person didn't work out, and it's almost certainly a story that flatters the company. Your predecessor has a different story. You need to hear it. Yes, they might be bitter. Yes, they might have their own blind spots. But they also have information you can't get anywhere else, about the real dynamics, the real obstacles, the gap between what leadership says and what leadership does. If you take the job without hearing their perspective, you're making a bet based on incomplete information, and the missing information is exactly the stuff that might tell you to walk away.

And if you're talking to your future boss and they disparage your predecessor, that’s a giant red flag. Probe on it. Ask what the company learned. Ask what they're doing differently this time. Ask what support and resources you'll have that your predecessor didn't. If the answer is "we just need the right person," that's not an answer, even if you think you’re that person. That's the sound of a company that hasn't examined its own role in the failure and is hoping a new hire will magically produce different results from the same broken setup. The job might be real. Or it might be an impossible situation dressed up as an opportunity, waiting for its next occupant.

Breaking the Cycle

If you're a founder or CEO who's read this far and recognized something uncomfortable, the good news is that the cycle can be broken. But it requires a different kind of accountability than "I'll hire better." It requires looking honestly at whether you've built an organization where a senior product leader can actually succeed, not in theory, but in practice. That means asking whether you've given them real authority to make decisions, or just the appearance of it. Whether you've resourced the product function appropriately, or expected them to do more with less while engineering gets what it needs. Whether you're genuinely open to product perspectives that differ from your own, or whether you're just looking for somebody to execute your vision because your plate is now too full. Whether you've created clarity about what success looks like and how it will be measured, or whether you've left it vague enough that failure can always be attributed to the individual.

Most importantly, it means examining the story you tell about your previous product hires. If every one of them "didn't work out" for reasons specific to them, the common denominator isn't them. It's the role. It's the company. It's you. The hardest part of breaking this cycle isn't finding the right person. It's taking accountability for helping them be the right person.