Ask the Machine to Disagree With You

Here’s a habit that’s saved me from more bad calls than anything else I do with AI.

Before a decision I care about, I don’t ask AI to help me make my case. I ask it to tear my case apart. “Here’s what I’m planning and why. Argue the other side. Find the holes.”

It’s ruthless in a way people in the room won’t be — nobody’s worried about my feelings or their standing. The weak spot in my logic shows up in seconds, while I still have time to fix it instead of getting caught on it live.

Then I walk in already knowing my plan’s worst objection, and usually I’ve got an answer ready for it.

AI didn’t make me more confident. It made me harder to surprise.

Try it before your next big meeting. Ask the machine to disagree with you.