How Leaders Lose Their Curiosity

At some point, most leaders stop asking questions. Not because they get lazy, not at all. Because they get certain.

Certainty feels like control. Curiosity feels like risk. And risk, in a high-stakes environment, starts to feel like weakness.

Early in my career, I asked a lot of questions. Things like “Explain to me why all of this point-of-sale material is kept in this long closet?” and “Are we only sponsoring this sports event because ownership likes the team?” and “How do you open this wine bottle for the tasting?” (To be fair, it was the wine business.) These questions, though, they were more than just a fresh-out-of-film school marketing guy showing it was his first salaried job… these questions were fuel.

I was allowed to wonder, and encouraged to ask why things worked the way they did. And for the next several stops of my career (away from wine labels and into membership renewals, into conference attendance, into… not kidding… plastics), this maintained.

And then along the way I noticed, after awhile… the loftier the title, the room stops expecting you to be curious with all the questions.

They start expecting you to have the answers. And so, as is often the inclination, leaders start giving those answers. They’re fast. They’re polished and gleaming. Sometimes, they’re even convincing.

Each time, that mid-honing leadership reflex gets stronger: sound sure, even if you’re not.

And rest in peace, curiosity. Because you died. (Talking to the curiosity.)

The irony is that certainty kills exactly what makes a leader valuable: perspective. You stop exploring, experimenting, and you get so far away from the work and those that are closest to it.

Meetings become rehearsals instead of discoveries.

You become a broadcaster, not a receiver.

Here’s what it actually looks like when curiosity leaves the building:

• You interrupt insights because they conflict with your existing mental gymnastics and pirouettes that harken to your experience.

• You read data for confirmation, not discovery.

• You stop sitting in rooms where you’re not the smartest person.

• You delegate exploration to “innovation teams” like it’s a side hobby.

Should’ve put a NSFW warning here, because this illusion of mastery? Man, it’s seductive. Efficiency is sexy, even as it robs you of oxygen.

The best leaders I’ve ever had and those I know today ask better questions the longer they truly lead. They have already learned that curiosity doesn’t threaten authority… it proves maturity. They listen longer, not because they doubt themselves, but because they know experience distorts memory.

They model the behavior that keeps their teams honest: “Teach me something I don’t know yet.”

If you want to measure your leadership health, don’t count deliverables. Count questions. The moment you stop being curious, you stop leading at all… and just settle into maintaining.