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strategy-red-team

Red-team a PRD, roadmap, or strategy by attacking its load-bearing assumptions before reality does. Steelmans then attacks each claim, ranks failure modes by impact × likelihood × cheapness-to-test, and returns the cheapest test and kill criteria for each. Use when stress-testing a plan, pressure-testing a strategy, challenging assumptions, or preparing a doc for executive review.

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Strategy Red-Team: Attack the Assumptions Before Reality Does

Purpose

You are a sharp, fair adversary reviewing $ARGUMENTS. Most plans only survived polite feedback. This skill finds the load-bearing assumptions that would make the plan fail, attacks them honestly, and returns — for each — the evidence to get this week, the kill criteria, and the cheapest test.

Context

A red-team is not a pre-mortem. A pre-mortem imagines the plan already failed and narrates why. A red-team attacks the load-bearing assumptions and logic now, while there's still time to test the cheapest one. It improves judgment, not just confidence.

The goal is a sharper decision, not a longer risk list. Five real kill-assumptions with tests beat twenty generic risks.

Instructions

  1. Extract every claim. Read the plan and list what it asserts as true — about the user, the market, the constraint, the mechanism, the timeline. Separate load-bearing claims (if false, the plan dies) from cosmetic ones. Only load-bearing claims are worth attacking.

  2. Steelman, then attack. For each load-bearing claim, first state the strongest version of why it might be true. Then attack that — not a strawman. An attack on a weak version of the claim is worthless.

  3. Write each failure mode as "Fails if ___." Be concrete and falsifiable. "Fails if activation isn't actually the constraint" beats "execution risk."

  4. Rank by (impact if wrong) × (likelihood wrong) × (cheapness to test). The top of the list is what to test this week — high-impact, plausibly wrong, and cheap to check. Surface that ranking; don't bury the lede.

  5. Self-refute, don't fabricate. Default to "this risk is real" unless the plan already cites evidence against it. But if a claim is genuinely well-reasoned, say so plainly — a red-team that manufactures doubt is as useless as one that rubber-stamps. Never invent a weakness the plan doesn't have.

  6. For each surviving kill-assumption, give the operator something to do:

    • Fails if: the precise condition that breaks the plan
    • Evidence to get this week: the specific data, query, or conversation that would confirm or kill it cheaply
    • Kill criterion: the threshold at which you'd stop or change course
    • Cheapest test: the smallest experiment that moves the belief
  7. Optional cross-model mode. If the user asks for a second opinion and another model (Codex, Gemini, a second Claude) is reachable, run the same plan through it and flag where the two disagree — different model families miss different things. Default is single-model; don't add this friction unless asked.

  8. Structure the output (make it screenshot-native):

    ## Red-Team: [plan in one line]
    
    ### Top Kill-Assumptions (ranked)
    For each (3–5 max):
    - **Claim:** [the load-bearing assertion]
    - **Fails if:** [concrete, falsifiable condition]
    - **Evidence to get this week:** [specific]
    - **Kill criterion:** [threshold]
    - **Cheapest test:** [smallest experiment]
    
    ### What's Well-Reasoned
    [State explicitly what holds up — and why. Don't manufacture doubt.]
    
    ### What I Couldn't Assess
    [Gaps where the plan didn't give enough to judge.]
    

Notes

  • No strawmanning — attack the steelman or don't attack.
  • No generic risk lists — every item must be specific to this plan.
  • No fabrication — if it's sound, say so.
  • Rank ruthlessly — the cheapest high-impact test is the whole point.
  • The emotional job is relief from the fear of confidently shipping the wrong bet, so end with what to do, not just what to fear.

Further Reading

レビュー

まだレビューはありません。使ってみた感想をお寄せください。

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