Claude’s first answer tends to be agreeable and one-sided. Make it fight itself.
The Prompt
Now argue against what you just said. What's the strongest
case for the opposite position? Where is your reasoning weakest?When to use it
- After Claude recommends a technical approach (“why might this be the wrong call?”)
- After Claude summarizes something (“what did you leave out or downplay?”)
- Before making any decision based on Claude’s advice
- When Claude agrees with you too easily (it does this a lot)
Variations
Steelman the other side:
Give me the strongest possible argument for the
approach you just recommended against.Find the holes:
Poke holes in your own answer. What assumptions
are you making? What could go wrong?Red team it:
You're now a skeptical reviewer. Attack this plan.
What are the top 3 reasons it would fail?Why you need this
Claude has a sycophancy problem. It wants to agree with you and confirm your existing beliefs. This prompt is the antidote. It forces Claude to think adversarially, which is where the real insights usually are.