The Best Leadership Newsletter Ever

The Best Leadership Newsletter Ever

🤖 AI Prompts

The AI prompt that predicts how you’ll fail

You've sabotaged good ideas before. This prompt tells you how you're about to do it again.

Sep 08, 2026
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I have completely sabotaged some really good ideas throughout my career.

Ideas I was truly excited about.
Ideas I was absolutely convinced were going to work.
In retrospect, they were ideas that probably would have been a huge success if somebody else had been in charge of them.

Unfortunately, I was.

Because when it comes to your next big goal or project, there are a thousand things that can screw it up. Bad timing. Bad assumptions. Other people. The economy. Money. Your horoscope on the day of the big meeting.

It could be anything.

But there’s one potential problem that you probably aren’t spending nearly enough time thinking about.

You.

You bring the same person, the same thinking and the same identity to every new project.

Your need for control. The way you get bored halfway through. Or how you expand one simple concept down so many different roads you’re not sure how to even get started.

Whatever your thing is, it comes with you. Always.
It’s like those leech-like sucker fish that attach to sharks. Wherever you swim, the sucker is still with you.

This is why I love the idea of a pre-mortem.

A post-mortem happens after something dies. You look back at the body and try to figure out what killed it.

A pre-mortem is much more helpful for people like you and me.

The basic idea is that you assume the thing you’re about to do has already failed. An embarrassingly spectacular failure.

Then you work backward and figure out what is going to kill it while you still have time to avoid the problem.

That’s what this week’s AI prompt does.

But wait… there’s more. Because isn’t there always?

The prompt doesn’t just ask AI to figure out what could kill your project. It asks AI to figure out how YOU are probably going to kill it.

And then it will tell you what to do before you even get the chance to screw up yet another great idea.

So don’t take one more step towards your project or goal, run this prompt first. Before you start. Otherwise, you’re just going to regret it and come back to me to tell me how you should’ve listened.

Don’t say I didn’t warn you.👇🏽

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