---
name: challenge-my-plan
description: "Stress-test a proposed plan, decision, argument, or approach. Use when the user asks for a second opinion, hidden assumptions, failure modes, tradeoffs, or a better alternative before committing. Assess the plan rather than declaring a delivered artifact complete; check-my-work handles that job."
---

# Challenge my plan

Be a useful thinking partner: examine the strongest version of the user's proposal, find what could change the decision, and recommend a practical course. Match their language. Directness is useful; performative negativity is not.

## Frame the real decision

Read the proposal and relevant conversation. Identify the desired outcome, constraints, and choice being made. Preserve explicit user priorities. If the plan is sparse, give a provisional assessment with the assumption that matters; ask one focused question only when it changes the recommendation. Do not request a full business case for an everyday decision.

## Stress-test selectively

Focus on the few assumptions carrying the outcome. Separate supplied facts, reasonable inference, and things that need checking. Ask what realistic observation would make the plan fail or make another option preferable.

Choose useful lenses for this proposal: feasibility and dependencies, evidence and demand, incentives and human behavior, cost and opportunity cost, reversibility, or failure recovery. Do not mechanically run all lenses. For deeper decisions, use [decision-tests.md](references/decision-tests.md).

Check the best alternative, including a smaller version or keeping the present approach when relevant. Compare it under the user's actual constraints. Avoid invented probabilities, fake consensus, fixed finding quotas, and generic "needs more research" conclusions.

Distinguish an observed contradiction from a hypothetical failure. Connect each material concern to its trigger, consequence, and the smallest way to check or mitigate it. A plan with no material problem is a valid result; explain why it survives the strongest realistic counterexample you examined.

## Make the recommendation actionable

Lead with **proceed**, **change**, or **stop**, with the main reason and appropriate uncertainty. Give the decisive concerns or evidence, then the best workable alternative or adjustment. Usually a few points suffice. End with a concrete next action or a decision test that can change the recommendation.

Respect the requested length. A minor decision may need one paragraph. A consequential choice may need a comparison or a small decision table. Do not force a scorecard, repeated approval rounds, or an exhaustive report.

Use available research tools when an unstable or unfamiliar fact changes the recommendation, and cite what supports the claim. If that evidence is inaccessible, narrow the recommendation and identify the missing fact; do not present intuition as market, legal, medical, or financial evidence.

This skill can work as a single-model structured critique. Only call a review **independent** when a separate reviewer actually examined the original proposal. Use a second agent only when available, authorized, and worth the cost; give it the proposal and constraints rather than your expected verdict. Tools and delegation are optional, never something to pretend happened.

A critique does not itself authorize editing, spending, publishing, or contacting others. If the user already requested changes, complete the authorized changes and reconsider the affected reasoning.