CEO Coaching: Curiosity vs. Certainty

As executives rack up experience, they naturally gain confidence. As they should.
The trouble starts when confidence quietly mutates into certainty.

Certain executives are often effective—and simultaneously dangerous. To themselves. To their teams. Occasionally to the business.

People who are certain don’t need more data. They don’t value dissenting voices. They will happily ignore evidence that contradicts their point of view. And here’s the kicker: with enough experience, they’re often right. Just often enough to reinforce the behavior.

But that same experience can blind them to changing circumstances, new information, and inconvenient facts. A very successful and creative CEO I know has a name for these folks: “The Flat Earth Society.”
Plenty of experience. Zero curiosity.

After working with a lot of experienced and confident CEOs—and more than a few chronically certain ones—I’ve come to believe this:

The buffer zone between confidence and certainty is curiosity.

Curious executives still make decisions. They don’t waffle or hide behind analysis paralysis. But they actively seek multiple sources of information. They invite dissent. They pressure-test their own thinking before the market does it for them.

When something feels familiar, they don’t default to “It worked before, so it must be right now.” Instead, they quickly scan new data, listen to smart people, and then decide. Same decisiveness. Better inputs.

You can spot the difference between curiosity and certainty in unexpected places.

Take a doctor’s office. Curious doctors ask better questions—and more of them. One of my favorite (now retired) physicians once said, mid-exam, “Huh. I wonder what that is?” Then he had me follow him to his office so we could look it up together. Confident. Curious. Refreshing.

You can also see it on a river (or a salt flat) with a fly rod in hand.

Certain anglers are often embarrassed. Curious ones solve the puzzle, adjust their approach, and catch more fish. Same river. Same conditions. Different mindset.

I’m a fan of process—not to create bureaucracy, but to enforce good behavior. If you feel your grip on certainty tightening, here are a few simple practices to reintroduce curiosity:

1. Surround yourself with people who think differently—and actually listen to them. Diversity of thought only works if you don’t immediately swat it away.

2. Before locking a decision, ask: “What else should we be considering?” Then wait. Silence is your friend.

3. Keep an “I Wonder” list. I’ve done this for years. When something puzzles me, it goes on the list. I use tools like ChatGPT to explore those questions when I have time. Block an hour or two a week. It’s surprisingly fun—and humbling.

4. When using AI, ask for the opposite answer. Then ask it to show you the verifiable data behind that conclusion. Treat it like a relentlessly polite contrarian.

As the saying goes, it’s what you know to be true that often gets you into trouble.

A healthy dose of curiosity is cheap insurance.