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GetDoolen Substack · Aug 21, 2026

Be the leader who is still thinking.

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Jon Doolen · GetDoolen Substack

The most dangerous leader in the room may be the one who always needs to have the answer.

Leadership isn’t about proving how smart you are.

It’s about remaining curious long enough to understand what is actually happening.

We live in a world that rewards quick answers.

Read the headline.

Watch the clip.

Form an opinion.

Pick a side.

Leadership demands something better.

Great leaders are willing to say:

“I don’t know yet.”

“Tell me more.”

“What am I missing?”

“Could both of these things be true?”

Those aren’t signs of weakness.

They’re signs of intellectual maturity.

As leaders grow, they begin to recognize that most problems involving people, organizations, customers and performance aren’t nearly as simple as we would like them to be.

Sometimes the employee who appears disengaged is overwhelmed.

Sometimes the person challenging your idea isn’t being difficult.

They see something you don’t.

Sometimes the process everyone wants to blame isn’t actually the problem.

And sometimes the leader needs to change their mind.

That’s where leadership gets interesting.

Your job isn’t to surround yourself with people who agree with you.

Your job is to create an environment where people are comfortable thinking with you.

Invite the disagreement.

Ask the second question.

Listen to the explanation you weren’t expecting.

Give people permission to challenge an assumption without challenging the relationship.

Most importantly, resist the temptation to immediately prove that you’re right.

Because leadership isn’t a contest to see who can reach an answer first.

It’s the responsibility to help people reach a better answer together.

Keep learning.

Keep questioning.

Keep listening.

Keep changing your mind when better information deserves it.

You don’t need to be the smartest person in every room.

Be the leader who is still thinking.

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