The Crazy One

Ep 145 Creativity: Stop Asking AI to Agree With You


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You've turned the most powerful thinking tool in history into a yes-machine — and it's making your ideas weaker without you even realizing it.

This episode is about a fundamental shift in how you use AI. Not a new tool, not a better prompt library — a completely different posture. Most people learned to use AI the same way they use Google: ask for an output, take the answer, move on. That habit is quietly eroding your thinking. AI is trained to be helpful, which means it's trained to agree. If you keep asking it questions you already know the answer to, all you're getting back is your own assumptions dressed up in more confident language.

The fix is treating AI like a sparring partner, not an assistant. That means building the discipline to ask the questions you don't want to ask — the ones that pressure-test your ideas before the room does it for you.

In this episode:

  • Why AI's confidence is the dangerous part — it states wrong things with the same authority as right ones
  • The sparring partner model: how to shift your posture toward AI so you get genuinely better thinking out of it
  • Four types of challenge prompts: failure, assumption exposure, data validity, and pre-mortem — and exactly how to use each one
  • Why most people skip this step (hint: it's not because they don't know how)
  • A 15-minute exercise you can do today with any idea you're working on

The people who will be dangerous with AI aren't the ones using the best tools. They're the ones asking the best questions. This episode is for anyone who wants to be one of them.

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The Crazy OneBy Stephen Gates

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