Chat + Project10 min setup

Stress-Test My Plan

Claude as rigorous sparring partner — identifying blind spots, generating alternatives, devil's advocate before your proposal reaches a wider audience.

Make this yours

When you do this, is there something really important to you?

Optional

Your answer shapes how the prompt is personalised. A few examples of what someone might write:

“I always want bullet points, never prose.”
“Push back if I'm being vague.”
“Keep updates under 5 lines.”
“Lead with the decision, not the analysis.”

Your input is sent to the model once and never stored.

0/500

I'm about to [describe what you're proposing]. Before I share this more widely, stress-test it.

**Your role:** You are a rigorous sparring partner, not a supportive coach. Your job is to find what's weak, not to validate what's strong. If something is genuinely good, say so briefly and move on. Spend your energy on the problems.

**What I need:**
1. **Blind spots** — What am I not seeing? What does this plan assume that could be wrong?
2. **Alternatives** — What's a meaningfully different approach I should have considered?
3. **Devil's advocate** — The strongest case against this. Not a strawman. The real objection someone smart and skeptical would raise.
4. **The one thing** — If I could only fix one thing before presenting this, what is it?

**My plan:**
[Paste your plan here]

Be direct. Don't soften. I'm not looking for encouragement.

Setup — 3 steps

Use a Project with your CLAUDE.md.

Running this in a Project with your CLAUDE.md means Claude knows your V2MOM and can flag when your plan diverges from what you've committed to.

Don't edit the output first.

Read the full stress test before deciding what to fix. The most uncomfortable critique is often the most important one.

Fix one thing, then re-run.

Address the single most important gap, then paste the updated plan back in. Run the stress test again. Iterate until the critiques are weak.

Make it yours — 2 variations

Public Version

Change the audience: "I'm presenting this to the board / to all-hands / to a customer." The stress test calibrates to the audience's likely objections.

Hiring Decision Version

Use the same structure for a hire you're considering. Replace "my plan" with the candidate profile. What are you not seeing? What's the risk?