strategy-red-team

name	strategy-red-team
description	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.

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 — high-impact, plausibly wrong, and cheap to check. Surface that ranking; don't bury the lede.