It doesn’t take long.

Sooner or later, someone leans across the table and asks, “So what do you think I should do?”

For a second, I know. Or at least I think I do.

I’ve sat in that chair. I’ve carried the pressure. I’ve survived the politics. I’ve made enough mistakes to have an opinion about almost everything.

A rising executive at a national telecommunications company came to me after taking on a bigger role. His relationship with his new manager was unraveling. Every conversation felt heavier than the last. He wanted to know what I would do.

I almost told him. It would’ve been easy. Useful, even.

Then I caught myself.

Easy has never been the point.

Instead, I asked him what he was assuming. He answered. I asked what he might be missing. He answered again. Then I asked one more question.

“What are you pretending not to know?”

Silence.

The room stayed quiet longer than either of us expected.

When he finally spoke, it wasn’t to answer my question. It was to answer his own.

He had stopped seeing his manager as a person and had started seeing her as an obstacle to overcome.

That changed everything.

Not because his manager changed.

Because he did.

Pressure gets loud.

Politics get loud.

Fear gets loud.

Other people’s expectations get loud.

By contrast, judgment is quiet.

If you don’t learn to hear it, you’ll spend your career mistaking volume for wisdom.

The senior executives I work with rarely need my judgment as much as they think they do.

They need to trust their own when pressure is loud.

Every leader eventually walks into a room alone. There is no coach beside them. No mentor. No consultant. No trusted friend. There is only the decision.

In that moment, my judgment won’t matter.

Only theirs will.

That’s why, when someone asks me what I think they should do, I usually answer with a question.

Three questions:

  • Whose voice has become louder than your own?

  • Where has pressure become so loud that you can no longer hear your own judgment?

  • What might you be pretending not to know?

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