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June 2026

The question under the question

Almost nobody books a first session about the thing we end up working on. That is not a criticism. It is just how it goes.

Someone comes to talk about a promotion and we spend the hour on what they think being senior will finally prove. Someone comes about a business plan and we end up on why they cannot ask anyone for help. The first question is real. It is also the door.

Why the first question is usually the safe one

We tend to lead with the version of a problem we already know how to talk about. It has a shape, it has a vocabulary, it makes us sound reasonable. The other question, the one that actually keeps you awake, has none of that yet.

Part of what a coach does is notice when the conversation has more energy somewhere else, and then ask about that instead.

Try this before your first session

Write down the thing you would book a session about. Then write down what you would say if you knew nobody would judge the answer. Bring both. We will start wherever you want, but it helps to know the second one exists.

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