You're not interviewing the company. You're interviewing the CEO who can burn your reputation down.

Every HR leader I know does the same thing when they're looking at a new role.

They study the scope. They research the company. They check the funding, the growth stage, the Glassdoor reviews.

And they treat the CEO as a footnote. A nice conversation at the end of the process. A vibe check. Most often, the CPO tells me they had a "great dinner" and he was really nice. Great.

That's the mistake.

I once took a role where the scope was exactly what I wanted. The company looked right on paper. And I left, because the CEO was the entire problem and no job description was ever going to save me from that.

Here's what HR leaders forget. We don't get to do our jobs at arm's length from the person at the top. Chief People Officers are the closest function to the CEO's worst instincts. We execute the layoffs they decide on. We deliver the PIPs they want. We manage the exits they order. We're the ones in the room when they make the call, and we're the ones whose name is on it when it goes badly. Ever heard of "disagree and commit?" That happens a lot as a leader, but the CPO really gets burned for it because they also represent the employees, not just the company.

Remember, CEO doesn't just set your working conditions. They spend your credibility.

Look at how this profession gets talked about. Every few months a founder or VC publishes a hot take about how HR is broken, bloated, or unnecessary. Harry Stebbings did it. Got a lot of engagement. And the irony is that half the time the thing they're blaming HR for was a CEO decision HR was told to carry out. The CEO sets the strategy, HR executes it, and when it lands badly, HR is the one left holding the reputational bill. We get blamed for the very things we didn't decide.

That's the dynamic you're walking into when you pick a CEO. When they make a call that violates everything you stand for and you're the one who has to deliver it, the market doesn't blame the CEO. It blames you. You become the HR leader who ran the brutal layoff, who tolerated the toxic founder, who looked the other way. The CEO keeps raising. You wear it.

So when you're evaluating your next role, the order is backwards. The CEO is not the last question. The CEO is the first one.

Ask yourself whether you actually respect how this person makes decisions. Whether their values survive contact with pressure. Whether they'll own the hard calls publicly or quietly let you take the hit. Whether you'd be proud to have your name attached to theirs when things get ugly, because they will get ugly.

A great scope under a CEO you don't trust is a trap.

A modest scope under a CEO whose judgment you'd stake your name on is a career.

So before you sign, ask yourself the real question. If this CEO makes the worst decision of their tenure, are you willing to have your name on it?

What's the one CEO red flag you ignored that you'd never ignore again?


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06/14/2026