Ask the AI to argue against your proposal
Before you send a proposal, ask the AI to play devil's advocate. It lists weak points and objections so you can fix them first.
Is this a good proposal?
I'm proposing that our team switch from weekly status meetings to a written update every Monday, with one live meeting a month. My proposal is below. Play devil's advocate. Argue against it as a skeptical department head would. Give me: 1. The three strongest objections, ranked by how likely they are to sink the idea. 2. Any assumptions I'm making without evidence. 3. What data or examples would make the case more convincing. Be direct. Don't soften the criticism or tell me what's good about it. """ [paste your proposal] """
Why it works
Ask an AI "Is this good?" and it tends to agree with you. Giving it the job of devil's advocate makes disagreement the task, so it looks for gaps instead of reasons to approve. You hear the objections while you can still fix them, not in the meeting.
Try it now
Click a highlighted part and type your own details. Press Enter to jump to the next one, then copy.
I'm proposing [your idea]. My proposal is below. Play devil's advocate as a skeptical [who will decide]. List the three strongest objections, the assumptions I haven't backed up, and what evidence would make my case stronger. Be direct and don't soften it. """ [paste your proposal] """
Variations
Then help me fix it
For each objection you raised, suggest one sentence I could add to the proposal that answers it.
Pressure-test the numbers
Look only at the numbers and estimates in my proposal. Which ones look optimistic, and what would happen to the case if each one were 25% worse?
See it from both sides
Write the best one-paragraph case for my proposal and the best one-paragraph case against it, then tell me which is stronger and why.
Based on: arXiv (Ethan Mollick and Lilach Mollick), "Assigning AI: Seven Approaches for Students, with Prompts". Last checked October 3, 2026.
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