Wick Red Team

Wick — Red Team

Updated: 2026-04-20 · first written 2026-04-20

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:

1. What's the strongest objection a domain expert would raise?
2. What's the most damaging failure mode if it unfolds as intended?
3. What load-bearing assumption is most vulnerable to being false?
4. What's the simplest way this gets leaked, gamed, or broken?
5. 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-team followed by /decide → stress-test before committing
• /steelman followed by wick-red-team → full adversarial examination
• wick-red-team before a major presentation → surface objections the audience would raise