The new chief operating officer had been at the company for nineteen years. He knew which regional director would call him at home on a Sunday, which of the plant managers padded their numbers by a week, and the exact reason the ERP migration had stalled back in 2019. In the room where they announced him, three separate people used the word earned. What nobody said out loud, and what he told me a month later in a conversation with nothing cheerful in it, was that he had never been a chief operating officer, had never watched anyone do it up close, and could not tell whether the nineteen years were an asset or a very expensive habit.

He is the ordinary case rather than the strange one. When Spencer Stuart mapped the nine most common functional roles across S&P 500 C-suites, using a snapshot of who occupied those seats as of the middle of 2025, 59 percent of them had been promoted from inside their own company.1 Among chief operating officers the figure reaches 80 percent, and among chief executives, 76.1 The firm reads this as proof that internal pipelines are working, which is a comfortable reading for a business that sells executive search and succession advice. Set the framing aside and look one column over in the same table. Twelve percent of sitting COOs had ever held the role before. Sixteen percent of CEOs.1

Two facts that only mean something together

Neither number is troubling on its own. Companies ought to promote from within, and a first-time COO is no scandal, because somebody has to do the job a first time. What makes the pair worth staring at is that they describe one person. The organization chose my nineteen-year man because it had nineteen years of evidence, every bit of it about a job that is not this one. Each promotion along the way confirmed something true and steadily narrower, which is that he was excellent at operations inside this particular building, with these particular people, under assumptions nobody had questioned since before the migration stalled. Real knowledge, all of it. It is also the reason the company cannot see what it is missing, since the evidence it trusts most is evidence about the wrong role.

A long internal record tells you what someone has been rewarded for. It tells you almost nothing about how they will do the first time nobody in the building has done the job either.

Settling into the leaders you already have

The churn above him has cooled without going quiet. Challenger, Gray & Christmas counted 521 announced CEO exits in the first quarter of 2026, down 19 percent from the same quarter a year earlier and still the third-highest first quarter in the twenty-four years the outplacement firm has tracked the number.2 Andy Challenger summed it up by saying companies are settling into the leaders they have.2 Follow that sentence to its end and notice who those leaders are. Three times out of four, the person the board is settling into is someone the company already had, now doing a job they have never done, and the settling is happening in an era when the average COO gets 3.3 years to prove the bet, the shortest run of any seat at the table.1

What the reps actually are

I keep returning to a stretch of work from years ago where nobody's background matched the assignment. Five civilian contractors dropped into a combat zone, handed a problem running above eight hundred hostile incidents a month. None of us had done that job. There was no version of it to have done. Twelve months later the number sat under fifty, and prior experience had nothing to do with it, since none of us had any to draw on. What moved it was pushing accountability out to the people closest to the information, and the fact that nobody in that arrangement had a function to protect.

That is the part an internal record cannot measure. A nineteen-year climb rewards the defense of a function, again and again, because defending a function is precisely what a good functional leader does. Then the job changes and the same person is asked to carry the whole enterprise, which means giving away the exact thing every prior promotion was granted for. The reps that matter were never reps at being a COO. They are reps at being wrong in front of people who report to you, at handing a decision to someone who knows more than you do about it, at watching a number you used to own get worse for a quarter because you stopped protecting your old team's share of it. Hardly anyone accumulates those on the way up. Hardly anyone gets asked about them on the way in.

So the conversation worth having with him was never about whether he was ready, which is unanswerable and a little cruel besides. It was narrower than that. What did the climb teach you to defend, and are you willing to find out what happens when you stop? He had the answer faster than I expected, the way most of them do. The harder question sits above him, with the people who made the appointment and never asked, because the promotion was allowed to stand in for the asking. What did your own rise train you to protect?