Use AI to review your document for the strongest possible objection someone could raise against it.
Before you send out a proposal, recommendation, or any document where someone might push back, ask AI to become your toughest critic. Give it your draft and have it argue against your main point as convincingly as possible—not to tear you down, but to show you exactly where your argument is weakest. This is like having a debate partner who's read your work and knows exactly where to poke holes. Once you see the strongest objection clearly, you can address it directly in your document, add supporting evidence where it's thin, or soften claims you can't fully back up. This transforms your work from something that might fall apart under scrutiny into something that's already anticipated and answered the hardest questions. It's especially powerful before budget requests, policy changes, vendor recommendations, or any situation where someone with authority will be looking for reasons to say no. You'll walk in knowing you've already handled their best argument.
Try this prompt today
“I'm about to share the document below. Your job is to argue against my main recommendation as strongly and convincingly as possible. Find the weakest parts of my argument, the claims I haven't fully supported, and the questions I haven't answered. Tell me the single most persuasive objection someone could raise, and explain exactly why it would work. Here's my document: [paste your draft]”
March 11, 2026
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