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Why I Trained ChatGPT to Challenge Me

Corey Brown
Corey Brown

Robots

I use ChatGPT nearly every day. It helps me move faster, but more importantly, I’ve trained it to make me think harder, too.

Many people use AI to generate content, answer questions, or brainstorm ideas. But the most valuable role it plays in my workflow is simpler, and far more powerful: it helps me push back on my own thinking.

The Risk of AI Always Agreeing With You

One of the easiest traps to fall into with AI, especially large language models, is how readily it agrees with you. Say something confidently, and it will often affirm your logic, even if it’s shaky. That’s a problem, particularly in my work (editorial strategy), where critical thinking is the real edge.

I don’t need an assistant that nods along. I need a partner that pushes back.

That’s why I gave ChatGPT this prompt. It’s a standing instruction, permanently pinned in my system.

The Prompt I Use with ChatGPT

From now on, don’t just agree with me or assume I’m right.

I want you to be a sparring partner, not a rubber stamp. When I share an idea, do the following:

  1. Check my assumptions. What might I be taking for granted?
  2. Push back. What would a smart skeptic say?
  3. Test the logic. Are there weak spots or leaps?
  4. Offer other angles. What else could be true?
  5. Correct me. Be direct. Don’t hedge. Tell me where I’m off, and why.

Be constructive but tough. Your job isn’t to argue for the sake of it. It’s to improve my thinking.

If I’m drifting into bias or lazy logic, call it out. We’re not just trying to land on good ideas. We’re trying to get there the right way.

What the Prompt Changed

I’ve used this prompt to:

  • Rethink a headline that was too predictable.
  • Pressure-test a content strategy assumption I hadn’t questioned in months.
  • Uncover gaps in my logic before sharing ideas with my team.

Sometimes, the best response I get from ChatGPT starts with:
“Have you considered that you might be missing X?”

And that’s exactly the point.

This isn’t about working faster. It’s about thinking better.

Why I Use AI This Way

I don’t use ChatGPT to write articles.

I don’t use it to replace editorial judgment.

I use it to challenge my assumptions, before anyone else has to.

If you work in a field where thinking clearly matters — and that includes most of us — you may find this prompt just as useful. Copy it, adapt it, or build your own version.

It changes the conversation.

Photo by JThomasShaw

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