Advanced TipGeneral Workplace

Use AI to review your proposal or recommendation for all the objections people will raise before you present it.

You've written a proposal, recommendation, or pitch. It feels solid to you. But you're not the one who has to approve it, fund it, or say yes. Before you send it, ask AI to play the role of the toughest critic in the room — the person who will push back, ask hard questions, or find reasons to say no. Give AI your draft and ask it to generate every objection, concern, or question someone might raise. Then use that list to strengthen your case before anyone sees it. This works especially well before budget requests, policy changes, new initiatives, vendor recommendations, or anything that requires buy-in from people with different priorities. You'll catch weak spots in your logic, missing details, or assumptions you didn't realize you were making. You can add a section that preemptively addresses concerns, rewrite unclear parts, or gather the data you're missing. By the time you present, you've already rehearsed the hardest questions — and your proposal feels bulletproof. The result: fewer surprises in the meeting, stronger credibility, and a much better chance of getting to yes. You've done the work of anticipating resistance, which means you walk in prepared instead of defensive.

Try this prompt today

I'm about to propose the following to [describe your audience: leadership team, department head, budget committee, etc.]. Please act as a skeptical reviewer who wants to protect resources and avoid risk. Read my proposal below and generate a list of every objection, concern, tough question, or reason someone might say no. Be specific and realistic. [Paste your proposal, recommendation, or pitch here]

March 1, 2026

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