“The higher you rise, the fewer people tell you what they actually see.”
The 2 a.m. Replay
It's late. The house is quiet. And you're replaying a conversation from earlier in the day.
Maybe it was the feedback you gave that landed badly. Maybe it was the decision you made too quickly, or the one you keep postponing. You turn it over again and again. You rehearse what you should have said. You draw conclusions, then second-guess them.
And you do all of it alone.
If that sounds familiar, you're in good company. Nearly every leader I coach has some version of this ritual. It's one of the most universal experiences in leadership, and one of the least discussed.
The Paradox of Rising
Here's the peculiar thing about leadership. The more responsibility you carry, the more solitary your thinking becomes.
Early in your career, reflection happens naturally. You debrief with peers over lunch. You ask your manager what they would do. You have colleagues at your level who are wrestling with the same problems.
Then you get promoted. And promoted again. Slowly, the circle of people you can think out loud with begins to shrink.
Here's the peculiar thing about leadership. The more responsibility you carry, the more solitary your thinking becomes.
Early in your career, reflection happens naturally. You debrief with peers over lunch. You ask your manager what they would do. You have colleagues at your level who are wrestling with the same problems.
Then you get promoted. And promoted again. Slowly, the circle of people you can think out loud with begins to shrink.
The result is a kind of quiet epistemic isolation. You still have plenty of information. What you lack is a place to examine it with someone else.
This matters more than most leaders realize. When we think alone, our blind spots stay blind. Our assumptions harden into facts. Our stories about people calcify before we've tested them. We become, without meaning to, the least objective observer of our own leadership.
What Coaches Know About This
In the coaching profession, we have a name for the antidote. It's called supervision.
The word sounds hierarchical. It isn't. Supervision is a confidential, collaborative space where a coach reflects on their own practice with a trained partner. Nobody is grading anyone. Nobody is handing out answers.
Instead, a supervisor helps you see what you're too close to notice. Why did that session leave me unsettled? What was I avoiding when I changed the subject? Whose voice was really in my head when I made that call?
In coaching supervision, we often talk about looking at a situation from several vantage points. There's what happened with the client. There's what happened inside the coach. And there's the wider system both of them live in. Most of us only ever look through one of those windows.
Now translate that to leadership. You don't need a credentialed supervisor to benefit from this discipline. What you need are its three essential ingredients:
That's it. Simple to describe. Surprisingly rare in practice.
Building Your Own Reflective Space
So how do you actually create this for yourself? Here's what I've seen work:
Choose the right person
Look outside your reporting line. A peer in another function. A former colleague who now works elsewhere. A mentor. A coach.
The credentials matter far less than two qualities. First, they should have no vested interest in what you decide. Second, they should have enough candor to challenge you. A thinking partner who only validates you is a mirror, not a window.
Protect the rhythm
Thirty minutes every few weeks beats a two-hour marathon once a year. Reflection is cumulative. Its benefits compound slowly and then all at once.
Put it on the calendar like any other commitment. Treat it as sacrosanct. The moment it becomes optional, it quietly disappears.
Bring the messy material
This is where most leaders falter. It's tempting to bring the polished version. The success story. The problem you've already solved.
Resist that impulse. Bring the meeting that felt off and you can't explain why. Bring the person you can't quite read. Bring the decision you still feel ambivalent about. That's where the learning lives.
Questions to Sit With
Before you close this tab, take a moment with these:
For your reflection
When did I last talk through a hard decision before making it?
Who in my life tells me the truth, even when it's inconvenient?
What situation am I currently carrying alone that I don't need to?
The Quiet Payoff
Something shifts when you stop thinking alone. Your decisions get cleaner. Your reactions get quieter. You begin catching your own patterns before they cost you anything.
That's metacognition in practice. Thinking about your thinking. It's one of the least glamorous leadership skills, and one of the most consequential.
You spend your days creating space for other people to grow. You deserve that same space for yourself. Not as an indulgence. As a responsibility to the people who depend on your judgment.
So here's my invitation for the rest of October. Find your person. Book thirty minutes. Bring one thing you haven't resolved.
