The Cost of Cool

Five years ago Kevin Hart was on Joe Rogan. They talked about Kevin’s audiobook, The Decision, and what motivated him to write it.

His thesis: your life is the sum of your decisions. If you want a different future, you have to train your mind with the same discipline and intensity you train your body.

During the conversation, Kevin told a story about being in the same room as Jeff Bezos, someone he’d never met. His friend immediately told him to…

Play it cool.

Of course, he did not.

In this clip, Kevin walks right over to Jeff and says:

“Hey Jeff. I’m Kevin Hart. How are you doing, man? … I admire you. I don’t know anything about your world in depth, but I admire you.”

That’s it. No posturing. No calculation. Just curiosity and respect.

Most people would have waited for the right moment (if they got one). Kevin made one.

The higher you go, the easier it is to mistake composure for confidence and start guarding your image instead of showing your interest. But Kevin didn’t need to act any other way other than how he genuinely felt.

That’s the distinction that makes his reaction important. He’s not a rookie trying to prove himself; he’s a seasoned pro showing that real confidence doesn’t need armor.

Seniority doesn’t require self-protection. In fact, it needs the opposite.

When you’re secure enough to stay curious, ask the question, show enthusiasm, or admit you don’t know… you unlock something most people lose with time: deeper, more meaningful relationships.

It’s the same for Chiefs of Staff.

The job isn’t to know everything. It’s to find out everything. To stay curious when others have stopped asking.

When you’re genuinely interested, people can tell. It changes how they show up around you. The Head of Comms drops by with a quick context check before the CEO’s next meeting. The HR director forwards a note you didn’t know you needed. The CFO flags a subtle change in tone from your principal before it ever becomes a problem.

None of that happens because you asked for it. It happens because people trust your curiosity.

They know you’re not collecting information, you’re connecting dots. You’re trying to understand how the business moves so you can help it move better.

Information lives in people and people only share with those who care.

But curiosity doesn’t keep itself alive. It fades quietly until you realize you’re finding out things later than you used to…

Ann Hiatt once told a story from her early days working for Marissa Mayer.

Marissa had been double-booked. Ann had scheduled her for one meeting, not realizing another important one with Eric Schmidt was already set. By the time she found out, it was too late for Marissa to attend. Marissa was furious. Not because of the conflict itself, but because Ann should have known.

It took Ann a while to understand what she meant. She hadn’t missed the meeting because she wasn’t paying attention. She’d missed it because she didn’t yet have the relationships that would have kept her in the loop.

She hadn’t spent enough time getting to know the other assistants, coordinators, and chiefs who traded information informally. The people who would’ve said, “Hey, heads up. Eric and a few others are meeting for dinner.”

That’s what happens when curiosity goes quiet. You stop investing in the human network underneath the org chart. You start assuming formal systems will catch what relationships used to.

And the longer you’ve been in the room, the easier it is to forget that awareness doesn’t live in meetings, emails or seniority. It lives in people and conversations between.

When curiosity dies, so does proximity. And proximity is power.

Curiosity is a discipline.

It looks like sending the extra follow-up when everyone else moves on. It sounds like asking a question you could probably Google. It’s walking down the hall instead of writing an email or Teams (Slack) message.

It’s the small, unglamorous stuff that no one sees that keeps you connected.

The best Chiefs I know are quietly relentless about this. They listen for the gaps as well as the headlines. They check in even when there’s no agenda. They build relationships that aren’t transactional, because they understand that awareness doesn’t scale through systems. It travels through trust.

And they do this naturally. They’re naturally interested in people and genuinely find ways to connect without an agenda.

You can’t automate that. You can’t delegate it. You have to be it to earn it. Even when you’re busy. Even when you think you already know.

Kevin Hart didn’t need anything from Jeff Bezos. But he knew what an opportunity to connect looked like.

Because when you stop needing to look like you know, you actually start learning again. You hear things you wouldn’t have. You connect in ways you didn’t expect.

That’s your edge.

Curiosity keeps you close to the truth. Relationships, not access, are what keep you informed, and an asset.

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