Use AI to review your proposal or recommendation and identify the objections people will raise before you submit it.
Before you submit a proposal, recommendation, or business case to decision-makers, use AI to stress-test it from the perspective of skeptics. Ask it to find holes in your logic, spot missing information, and predict the objections or pushback you'll face. This gives you time to strengthen weak points, add supporting details, or prepare responses before anyone actually says no. It's like having a skeptical colleague review your work first—except AI won't sugarcoat what's missing.
Try this prompt today
“Act as a skeptical senior decision-maker reviewing a proposal. I'm going to share a recommendation or proposal I've written. Your job is to identify: (1) weak points in my argument or logic, (2) missing information or data that someone would want before saying yes, (3) objections or concerns a cautious or budget-conscious leader would raise, and (4) questions I haven't answered yet. Be direct and specific. Here's my proposal: [Paste your proposal, recommendation, or business case here]”
March 21, 2026
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