The Best Leadership Newsletter Ever

The Best Leadership Newsletter Ever

🤖 AI Prompts

Have the conversation before you have the conversation

The AI prompt that lets you find out what you're going to screw up before you actually screw it up. It’s time to have the conversation before you have the conversation.

Oct 20, 2026
∙ Paid

You can’t practice for a tug-of-war without somebody on the other side pulling back.

But that’s exactly how most of us prepare for difficult conversations.
We rehearse what we’re going to say.
We work through our arguments.
We imagine all the brilliant responses we’re going to give when the other person pushes back.

And, of course, we always win.
Because we’re playing both sides.

We think we’re preparing for a conversation. We’re actually preparing to deliver a speech.

And there’s a big difference between the two.

But I figured out a solution.
I figured out how to have the entire conversation before actually having the conversation.

And it’s already saved me from making a fool of myself.
Here’s what happened.

I’ve got a meeting this week with a publisher about my upcoming book.

I’ve been thinking about this conversation for weeks. I know what I want. I know why it makes sense. I’ve got my arguments all worked out in my head.

So I built an AI prompt to play the publisher.
And I had the conversation three days before the actual conversation.

It sucked.
She asked questions I hadn’t thought about at all.
She challenged my assumptions that I fully believed were reasonable.

I even gave a long monologue that had sounded brilliant in my head, and like complete buffoonery when it came out of my mouth.

Which is exactly what I needed.

Because now I can change what I plan to say.
And I can try it again.
And again.

And here’s my favorite part.

Whenever the conversation starts going sideways, I just type three words:

I LOVE PIZZA.

AI immediately drops the character and tells me what I did well, what I screwed up, and what I should do differently.

Then I can jump right back into the conversation.
Or start over.
Or make the person even more difficult to talk to.

I dare you to try doing that with your boss.

So what’s your next big conversation?

Maybe you’re asking your boss for a raise.
Maybe you’re confronting an employee who’s not performing.
Maybe you’re pitching an idea to someone who has already told you no.

You can keep rehearsing both sides of the conversation in your head.
Or you can finally find out what happens when someone pushes back.

Here’s the prompt. 👇🏽

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