Bring a decision, not a request for reassurance
“Is this a good idea?” invites a vague response. Describe the decision, your options, what matters, and what you do not know. Ask the assistant to summarize your reasoning before challenging it. You should be able to correct its understanding.
Ask for a fair challenge
Request the strongest case against your preferred option, a plausible alternative, and the evidence that would change the recommendation. Do not confuse a persuasive response with independent evidence. The assistant may miss context or mirror how you framed the question.
Use a decision table
Compare the same criteria across options: user value, effort, dependencies, reversibility, and uncertainty. Supply your own evidence. Tell AI to mark unknowns and avoid invented scores. A table helps expose the tradeoff; it does not remove the need to choose.
End with a real next step
Choose one action that reduces uncertainty. That could be a conversation, a prototype, or checking a source. Record your choice and why. Revisit it when new evidence arrives rather than treating the conversation as a final verdict.
Make it yours
Bring a small, reversible decision. Ask for the best objection to your preferred choice, then identify one piece of evidence you could gather this week.