Prompting Skills playbook/Module 6 · Thinking with AI

Day 52 / 100 · Thinking with AI · Devil's advocate

Argue with me.

Ask AI to attack your idea before your customers, your board or reality does.

Steelman

The Other Side

“Make the strongest possible case against my plan.”

Not a straw man. The best argument a smart critic would make.

Pre-mortem

Imagine It Failed

“It's a year from now and this failed. Why?”

Failure stories surface risks that optimism hides.

Stakeholder hats

Who Pushes Back

“Critique this as finance, then ops, then a customer.”

Each seat sees different holes.

Find the holes before your customers do.