The Best Leadership Newsletter Ever

The Best Leadership Newsletter Ever

đŸ€– AI Prompts

The 7 Prompts That Replace a $300/Hour Therapist

These 7 AI prompts uncover the fears, lies, and patterns shaping your behavior without you even realizing it.

Jun 02, 2026
∙ Paid

Therapy is expensive.
I’ve sunk a lot into it over the decades.

But great therapy actually changes things (which is why I’m flattered whenever my executive coaching clients call me their leadership therapist.)

I’m not here to tell you to fire your therapist. However, there’s something you need to know if you don’t know already.

When you ask AI the right questions in the right way, you’ll be able to see into your blind spot infinitely more clearer and faster than any therapist can ever provide.

The catch? Most people don’t know how to ask the right questions.

Well, my friend, that’s why we’re here together. I gotchoo.

Here are 7 of the most important prompts to help you understand your behavior better than a weekly $300 therapy session will ever provide.


1. The Other Perspectives

You’re in a situation that’s stressing you out - but you can only see it one way. Your way. That’s not a thinking problem, that’s a perspective problem. This prompt gives you three other ways to look at your specific situation - then it points to the one you’re resisting the hardest. Turns out, that’s usually the one that will allow you to exhale.

Here’s a situation that’s been stressing me out: [describe it in a few sentences]. Before you respond, ask me two questions to understand it better. Then show me three other ways to interpret what’s happening that I probably can’t see right now — and tell me which one I’m most resistant to, and why that might be the important one.


2. The Energy Audit

Your tired. You’re drained. You think it’s the workload or your commute or lack of sleep. It’s probably something else.

This prompt goes through your week and finds what’s really draining you. It’s almost never what you think.

I want to understand what’s actually draining me. Ask me to walk you through my last week — work, people, habits, all of it. Ask follow-up questions where something stands out. Then tell me what’s really depleting me, and what I’ve been blaming instead of the real cause.


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3. The Stuck Point

There’s that something you’ve been “thinking about” for weeks. Maybe months. But you’re not actually thinking — you’re circling. Something specific is holding you back, and you probably can’t name it. This prompt names it for you
 and tells you if your waiting is worth it.

I’ve been stuck on something: [describe the decision or situation]. Don’t give me advice yet. Ask me a few questions about what’s actually keeping me in place. Then tell me what I’m really waiting for — and whether it’s ever actually going to arrive.

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