In more than thirteen years of sitting in rooms with CEOs, I've never met one who didn't, somewhere underneath, quietly wonder whether they were actually good enough for the job.
Not one. The most successful person at the table, the one with the growth chart everyone else envies, carries it too. They've just gotten better at hiding it.
The doubt doesn't go away with revenue. It doesn't go away with a bigger title or a clean exit. It goes quiet, it goes underground, and most leaders spend an enormous amount of energy making sure no one ever sees it.
That energy is the waste. Not the doubt, the hiding.
Tim Ferriss, the writer and investor, has said imposter syndrome is one of his superpowers. Sit with that, because it sounds backwards. How is a feeling of inadequacy an advantage?
Here's how. When you quietly accept that you might not have all the answers, you give yourself permission to ask the question you were afraid would expose you. The basic one. The "explain that to me again" one. The one half the room is also wondering about but is too worried about their own standing to ask.
The leader who needs to be the smartest person in the room asks the fewest questions. The leader who has made peace with not knowing asks the most. The questions are where the learning is.
This matters more than it used to. The pace of change (AI most obviously, but not only AI) means the half-life of what you know is shorter than it's ever been. The expertise that got you here is depreciating faster than it used to. In that environment, "I don't understand this yet, walk me through it" isn't a weakness to manage. It's a competitive advantage.
Andy Grove titled his book Only the Paranoid Survive. He didn't mean fear. He meant the discipline of never assuming you've got it figured out. Imposter syndrome, pointed in the right direction, is the same instinct. It just feels worse from the inside.
There's a quieter benefit, too. When a CEO asks the honest question (i.e., when the team sees the leader doesn't know everything), it gives everyone else permission to do the same. It tells the room that not knowing is allowed here. That's the soil real debate and real learning grow in. A leader who hides every doubt teaches the whole organization to hide.
So the goal was never to get rid of the feeling. You won't, and the attempt is exhausting. The goal is to change your relationship to it. The doubt is going to be there. You can spend your energy concealing it or you can let it keep you curious, humble, and asking. One of those costs you. The other compounds.
So: what would you ask — of your team, your peers, your advisors — if not knowing cost you nothing?
Published in the CEO Corner column, May 2026.
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