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.

1. Surface 3–5 hidden assumptions the plan rests on.
2. For each assumption, give a concrete scenario where it breaks.
3. Rank objections by severity (would-kill-the-plan vs nice-to-fix).
4. 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

Plan as I understand it: <one line>

Assumptions you're betting on:
1. <assumption> — <why this might be wrong>
2. …

Failure scenarios (ranked):
1. [Severity: would-kill] <scenario>
2. [Severity: would-hurt] <scenario>
3. …

What would change your mind?