Challenge

Challenge the Plan (Adversarial Pre-Implementation)

Run an adversarial pass against a proposed plan before any code is written. This catches wrong-direction work before it accumulates sunk cost.

The failure mode we are defending against: the AI writing exactly what was asked for — when what was asked for was wrong.

Takes a plan description via $ARGUMENTS. If $ARGUMENTS is empty, challenge the most recently discussed plan in the current session (or the current branch's diff if there is already code).

When to Use

Use aggressively for:

• New features touching shared types, API contracts, or DB schema
• Cross-service changes
• New library / framework / pattern adoption
• Anything architectural — anything that would be expensive to undo in three months
• Database migrations and RPC actions (per CLAUDE.md → Database Migrations & RPC Actions)

Skip for:

• Typo / formatting / 1-line bug fixes
• Docs-only changes
• Purely internal refactors with no interface change

When in doubt, run it. The cost is five minutes; the cost of building the wrong thing is much higher.

Step 0: Confirm There Is a Concrete Plan

Before challenging, confirm the plan is concrete enough to attack:

• Is the approach stated in one paragraph?
• Are the affected files / services / contracts named?
• Is the success criterion named?

If any of those are missing, stop and ask the user to sharpen the plan first. An ambiguous plan cannot be meaningfully challenged — you will end up arguing with straw men.

Step 1: Restate the Plan

In one paragraph, restate the proposed approach as precisely as possible. Include: the problem it solves, the approach, the affected services, and how you'd know it worked.

Step 2: Find Three Strongest Counterarguments

Produce exactly three independent reasons this plan is wrong. Not nitpicks — structural objections. Each counterargument must include:

1. The objection (one sentence)
2. The concrete risk it creates — what breaks, and when
3. The cost of ignoring it — cheap to fix later? or permanent?

Bar for a valid counterargument:

• "This might be slightly slower" — not a counterargument.

• "This forces a second round-trip on every request, which will 3x the P95 latency on the hot path used by the dashboard's overview page" — yes, this is a counterargument.

• "This is a bit complex" — not a counterargument.

• "This couples the collector-server directly to the ticket-server schema, so any ticket schema change will require a coordinated cross-service deploy" — yes, this is a counterargument.

If you cannot find three, you either (a) don't understand the plan well enough, or (b) the plan is actually fine for a trivial change — in which case, skip this skill.

Step 3: Future-Self Review

Answer these three questions plainly:

1. Six-month senior-engineer review: What would a senior engineer reviewing this diff six months from now criticize first? Be specific — name the pattern or smell.
2. Optimization trade-off: What does this plan optimize for, and what does it sacrifice? Every design trades something.
3. Simpler alternative: Is there a simpler approach that achieves ~80% of the benefit with ~20% of the complexity? If yes, state it. If the answer is "yes but we still want the full approach", explain why — that reason becomes part of the decision record.

Step 4: Verdict (Binding)

End with exactly one of these three verdicts. The verdict is binding. Implementation MUST NOT start on anything but PROCEED.

• PROCEED — The objections are real but the plan is still the right call. Note which objections to actively mitigate during implementation.
• REVISE — The plan mostly holds but needs specific changes before implementation. List the exact required changes. Re-run /challenge on the revised plan if any change is material.
• REDESIGN — One or more counterarguments are fatal, or a simpler alternative dominates. Do NOT implement this plan. Return to the research/strategy phase.

Step 5: Log the Decision

If the verdict is PROCEED and the change is architectural (affects shared contracts, schema, cross-service behavior, framework choice, or tooling), append one line to the root CLAUDE.md under ## AI Coding Principles → ### 4. Decisions & Lessons Learned → #### Architecture Decisions (removing the _No entries yet_ placeholder if this is the first entry). Format:

- **[YYYY-MM] {title}**: Chose {approach} over {alternative}. Why: {reason}. Counterarguments considered: {brief summary}. Reconsider if: {condition}.

If the verdict is REDESIGN and the plan had been seriously considered (not just a half-formed idea), append to ## Decisions & Lessons Learned → What We've Tried and Won't Try Again:

- **[YYYY-MM] {title}**: Considered {approach} for {problem}. Rejected because: {concrete reason from counterarguments}. Current direction: {replacement}.

Do NOT log day-to-day implementation details — only decisions that affect how future work should be done.

Output Format

Always output in this shape so the result is parseable and reviewable:

## Adversarial Review: {plan title}

### Restated Plan
{one paragraph}

### Counterargument 1 — {short title}
- **Objection:** ...
- **Risk:** ...
- **Cost of ignoring:** ...

### Counterargument 2 — {short title}
- **Objection:** ...
- **Risk:** ...
- **Cost of ignoring:** ...

### Counterargument 3 — {short title}
- **Objection:** ...
- **Risk:** ...
- **Cost of ignoring:** ...

### Future-Self Review
- **Senior-engineer critique (6 months out):** ...
- **Optimizes for:** ...
- **Sacrifices:** ...
- **Simpler alternative:** ... (or: "none found — full approach justified because ...")

### Verdict: {PROCEED | REVISE | REDESIGN}

{For PROCEED: which objections must be actively mitigated during implementation.}
{For REVISE: the exact required changes. Re-run /challenge if material.}
{For REDESIGN: a one-line pointer to what to explore instead.}

Anti-Patterns (Do Not Do These)

• Do not hedge. "This might be okay but could also be risky" is not a counterargument — it's a non-answer. Commit to a position.
• Do not invent objections. If you cannot find three real ones for a trivial change, the right move is to skip this skill, not to manufacture filler.
• Do not rubber-stamp. PROCEED on every run means the skill is broken. If you haven't emitted REVISE or REDESIGN in a while, check whether you're being critical enough.
• Do not start implementing after a REVISE or REDESIGN. Stop. Surface the verdict to the user. Let them decide the next move.