You're the worst judge of your own plan because you want it to work. This puts on the adversary's hat: it hunts for the weakest link, the optimistic hand-wave, the single point of failure, and the move a competitor or reality would make to knock it over — then hands you the fixes. Better a friendly attack now than a real one later.
What This Skill Produces
- The weak points — where the plan is most vulnerable, ranked
- The killer move — the single thing an adversary (or reality) would do to break it fastest
- The hope-it-holds part — the spot you're quietly relying on without proof
- Single points of failure — where one thing going wrong takes down everything
- The fixes — the specific changes that close the biggest gaps, prioritized
Required Inputs
Ask for these if not provided:
- The plan — what you intend to do
- The context — competitors, dependencies, who might oppose it
- What you're confident about — often where the weakness hides
- What "broken" means — the outcome you're trying to protect
Framework: Attack It Like You Want It To Fail
- Adopt the adversary's goal. Genuinely try to make the plan fail — a real red team, not a gentle review.
- Find the weakest link. Plans break at their weakest point, not their average — locate it.
- Name the killer move. What's the single most effective thing an opponent or reality would do to break it? That's your priority to defend.
- Expose the hopes. Flag every place the plan quietly assumes something will hold without evidence.
- Hunt single points of failure. Where does one failure cascade into total failure?
- Then hand over fixes. Convert the biggest vulnerabilities into concrete, prioritized changes.
Output Format
Red-teaming: [the plan]
Weakest points (ranked): [1, 2, 3]. The killer move: [what an adversary/reality does to break it fastest]. You're hoping this holds: [the unproven assumption you're relying on]. Single points of failure: [where one thing breaks everything]. Fixes (prioritized): [close the biggest gaps].
Quality Checks
- Genuinely adversarial, not a soft review
- Identifies the weakest link specifically
- Names the single most effective breaking move
- Exposes the unproven hopes
- Flags single points of failure
- Ends with concrete, prioritized fixes
Anti-Patterns
- A gentle review that pulls its punches.
- Listing generic risks instead of the killer move.
- Attacking the plan's strengths instead of its weak link.
- No fixes — just tearing it down.
Example Trigger Phrases
- "Red-team my business plan."
- "Attack this strategy — where does it break?"
- "Find the holes in my argument before I present it."
- "What's the weakest part of this plan?"
- "How would a competitor break what I'm building?"