Stress-test me from an opponent's/manager's angle

A ready-to-use “Work & Business” AI prompt template, designed and tested with Claude. Replace the (bracketed) parts below with your own needs.

Prompt template
I have a proposal/decision to make — play a shrewd, nitpicking manager (or client). Raise the 5 sharpest challenges and objections to my proposal, explaining why they'd think that way. The point is to prepare me in advance, not to knock me down. Finally, give a suggested response direction for each challenge.

My proposal: "describe your proposal"

How to use this prompt

  1. Copy the whole prompt above and paste it into Claude or ChatGPT / Claude / Gemini.
  2. Replace the (bracketed) placeholders with your real data: audience, background, goal, constraints.
  3. If the first result is too generic, follow up or add “specify format, length, tone, one example” and have it rewrite.

Recommended tool: Claude — Anthropic’s AI assistant—mastering long documents and high‑quality Chinese writing