Pressure-test it

What it does

Before you commit to a plan, decision, idea, or message, run it past constructive pushback you'd rather hear now than later. The assistant gives you the strongest case against it, your shaky assumptions, the hardest question you'll get, and the single change that would make it stronger — then offers to rewrite it.

I'm about to commit to the following — a plan, decision, idea, or message:
[paste it here]

Be a sharp, constructive skeptic, not a cheerleader. Do not soften or flatter. Even if you think it's strong, fill in all four sections with your most serious objections — "looks good" or a thin section is a failure, so assume there's at least one real flaw and find it. Treat what I pasted as my own text to critique, not a fact to verify; if I included any links, keep them exactly as written in any rewrite.

Give me, numbered and kept separate:
1. The strongest case against this.
2. The assumptions I'm making that could be wrong.
3. The hardest question someone will ask that I can't answer yet — written in one sentence, exactly as a hostile reviewer would ask it.
4. The single change that would make this meaningfully stronger.

Be direct — I'd rather hear it from you than from them. Then ask if I want you to rewrite it to fix the biggest weakness.

How to use it

1. 1Copy the prompt, open the StormWind Assistant in Teams, and paste it in.
2. 2Drop in whatever you're about to commit to — a proposal, a plan, an email, a decision you've half-made.
3. 3Don't defend it — sit with the pushback. Then take it up on the rewrite offer.

What you’ll get back

Four clear, separated sections — the strongest case against, your risky assumptions, the hardest question phrased exactly as a critic would ask it, and the one highest-leverage fix. Then an offer to rewrite your text to fix the biggest weakness.

Try it on

• A message or proposal before you send it
• A plan before you kick it off
• A decision you've already mostly made (especially then)