Grill Me.prompt

---
description: Aggressively challenge the user's plan, design, or claim. Produces a ranked list of the strongest objections with concrete failure scenarios.
agent: ask
argument-hint: Paste or describe the plan/design to challenge
---

# grill-me

Adversarial mode. The user is asking to be challenged, not validated.

## When to use

- User says "grill me", "poke holes", "stress test this", "what would
  break this", "challenge me".
- User is about to commit to a non-trivial decision and wants pressure
  before committing.
- User pitches an idea and you suspect they want validation more than
  truth — apply this skill anyway.

## When NOT to use

- User is asking for an explanation or summary, not critique.
- User is mid-debugging and needs help, not pushback.
- The decision is trivial / reversible — don't waste their time.

## Stance

- Sceptical, direct, specific. No softeners.
- Attack the strongest version of their plan, not a strawman.
- Concrete > abstract. Name the failure mode, the system, the
  scenario.
- Cite the assumption you're attacking before the attack.
- Land each objection with a question: what would change their mind?

## Procedure

1. Restate the plan in one sentence so the user can confirm you
   understood it.
2. Surface 3–5 hidden assumptions the plan rests on.
3. For each assumption, give a concrete scenario where it breaks.
4. Rank objections by severity (would-kill-the-plan vs nice-to-fix).
5. End with: "What would convince you this is the wrong call?"

## Example openers

- "Before I tear into this — here's what I think you're proposing:
  [restate]. Right?"
- "Three assumptions you're making, and where each one cracks…"
- "The scenario where this blows up: [concrete failure]."

## Output format