Attack the plan

Attack the Plan

Assume the plan is a mistake we will regret in six months. Argue that case as well as it can be argued, find where the opposition is right, and convert what survives into amendments — or a stop.

Inputs

• The plan: a design doc, spec, PR description, migration outline, or a verbal "here's what we're going to do"
• The context it lives in: codebase, constraints, team size, deadline

Steps

1. State the plan back in three sentences. What it does, what it replaces, what it bets on. If you can't, the plan is underspecified — that's finding #1, stop and say so.

2. Steelman the opposition. Write the strongest version of "this is the wrong move" — not weaknesses in the plan but the case against it: the alternative it forecloses, the assumption it can't survive losing, the simpler thing it's avoiding.

3. Attack by lens, one pass each. For each lens, name the concrete failure and the trigger that would expose it:

   • Correctness — where does it produce a wrong result?
   • Scale & load — what breaks at 10x? What was only tested at 1x?
   • Operations — how is it debugged at 3am? What's the rollback?
   • Security & data — what does it newly expose, log, or trust?
   • Product — does it solve the user's problem or the team's itch?
   • Six-month regret — what maintenance burden is being signed up for?

4. Separate severity from volume. Rank attacks: fatal (plan should not proceed as-is), amendable (proceed with a named change), accepted risk (proceed, monitor for a named trigger). Resist padding — three sharp attacks beat twelve vague ones.

5. Deliver a verdict, not a vibe. End with exactly one of: proceed / proceed with amendments (listed) / stop (with the cheaper alternative). Include, for each fatal attack, what evidence would change your mind — this keeps the attack falsifiable.

Conventions

• Attack the plan, never the planner. No hedging either — "this might possibly be a concern" is a review; "this fails when X, here's how" is an attack.
• If you find nothing fatal, say so plainly. A survived attack is real information; manufacturing objections destroys the signal.

Edge Cases

• You built the plan yourself. Best case for this skill — run it before presenting. Note in the output that author and attacker are the same agent, and consider a second independent attacker for expensive decisions.
• The decision is already made and shipped. Convert the attack into a monitoring checklist: the named triggers become alerts, not arguments.
• Deadline pressure. Run lenses 1 (correctness) and 3 (operations) only, and say the others were skipped.