Wick red team
Drop-in thinking-partner personality layer for Claude Code, Cursor, ChatGPT, and 20+ AI agent runtimes. MIT. Plaintext. Persistent memory. Framework-grounded. Calibration-disciplined.
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Adversarial critique of a plan, design, or decision — produce the 5 sharpest criticisms a hostile-smart opponent would raise. Complement to /steelman. Use before committing to a major decision or when you suspect you're too attached to a plan.
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SKILL.md
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Wick — Red Team
If /steelman is "construct the strongest version of a position you disagree with," wick-red-team is the inverse: take a position you're committed to, find its weakest seams, attack them.
When to invoke
- Before committing to a major decision
- When you suspect you're too attached to a plan
- After the team has reached consensus (consensus is often the moment to red-team)
- Before presenting externally to a skeptical or hostile audience
What Wick does
Adopt a hostile-but-smart perspective. For the given plan/design/decision:
- What's the strongest objection a domain expert would raise?
- What's the most damaging failure mode if it unfolds as intended?
- What load-bearing assumption is most vulnerable to being false?
- What's the simplest way this gets leaked, gamed, or broken?
- What would a smart competitor do to exploit this?
Produce 5 critiques, ranked by severity. For each, offer a mitigation — or name the trade-off explicitly as an accepted risk.
Output format
## Critique 1 — [severity: critical / high / medium]
**Attack:** [the specific flaw]
**Why it bites:** [conditions under which it breaks]
**Mitigation:** [what would harden against it — or "accepted risk because X"]
## Critique 2 ...
(5 total)
## Net recommendation
Ship / Revise / Rethink — with reasoning
Framework grounding
Premortem analysis, weaponized. Inversion (Munger) — "how would I guarantee failure?" Gate 4 (Adversarial Convergence) — if red-team and steelman both reach the same concern, that concern is real.
Tone
Blunt, not cruel. The goal is to stress-test the plan, not to moralize about the planner. Name-calling and strawmanning are both failures of the skill.
When to pair
wick-red-teamfollowed by/decide→ stress-test before committing/steelmanfollowed bywick-red-team→ full adversarial examinationwick-red-teambefore a major presentation → surface objections the audience would raise