Grill Me

Stress-tests a plan through structured adversarial questioning before any code is written. Models the plan as a design tree — every decision branches into the decisions that hang off it — and interviews the user in rounds until every branch is resolved and nothing is silently assumed.

Combines the phase discipline of the original with the frontier-rounds mechanic from mattpocock/skills' grilling.

When to Use

• User says "grill me", "interview my plan", "stress test this idea"
• Before complex work: auth flows, schema changes, migrations, payments
• A plan has unresolved decisions or seems vague
• Before subagent-driven-development decomposition

Do NOT use for existing code (use requesting-code-review) or simple one-off tasks.

Prerequisites

None. The skill works on any plan or raw idea.

Core Mechanic: Frontier Rounds

Map the plan as a design tree. The frontier is every decision whose prerequisites are already settled — the questions you can ask NOW without guessing at answers you haven't heard yet.

Work in rounds: ask the whole current frontier in one message, numbered, each question carrying your recommended answer. Then wait. A question whose answer depends on another question still open in this round belongs to a LATER round, not this one.

Format each round like so:

❓ Q1 — <question title>: <question body, options if relevant>
➡️ Recommendation: <your recommended answer + one-line why>

❓ Q2 — <question title>: <question body>
➡️ Recommendation: <...>

Each answer reshapes the tree: settled decisions push the frontier outward and unblock dependent questions. Recompute the frontier and ask the next round.

Facts are your job; decisions are the user's. When a frontier question needs a fact from the environment (codebase, filesystem, config, docs), find it yourself with search_files / read_file / terminal — or dispatch a subagent via delegate_task for a heavy exploration. Never ask the user for anything you could look up. Don't block on an exploration: only the questions downstream of it wait; ask the rest of the frontier now.

Question Coverage (work these branches into the tree)

Understanding — the real goal and boundaries:

• What is the ACTUAL objective? What is explicitly IN and OUT of scope?
• What are the constraints (time, tech, team, budget)? Who are the users?

Technical decisions — for each architectural choice:

• "Why this approach and not X?" / "What happens if Y fails?"
• "What's the worst case?" / "How would you roll back?"
• Cross-reference the existing codebase; if the project already has a pattern for this, call it out.

Edge cases:

• "What happens if the user does Z?" / "What if dependency X goes down?"
• "What if volume is 100x expected?" / "What are the security implications?"

Synthesis (when the frontier is empty)

1. Summarize ALL decisions in bullet points
2. List anything left open, and what is explicitly OUT of scope
3. Ask: "Aligned? Should I start implementing, or adjust anything?"

Do not act on the plan until the user confirms shared understanding.

Pitfalls

1. Asking questions out of dependency order. A question that depends on an unanswered question is a guess wearing a question mark. Keep it for a later round.
2. Skipping the codebase. Find facts in code with Hermes tools instead of asking the user.
3. Accepting "I don't know" as final. Suggest options, explain trade-offs, make a recommendation.
4. Writing code during the interrogation. Alignment only — code after the explicit green light.
5. Being too agreeable. Your job is to find problems. If everything looks fine, look harder.
6. Not adapting to the user's language. Interview in whatever language the user speaks.

Verification

• Every question in a round had all its prerequisites already settled
• Provided a recommendation with each question
• Explored the codebase for facts instead of asking the user
• Frontier empty (no branch silently assumed) before synthesizing
• Produced a clear summary of all decisions and open items
• Confirmed user alignment before stopping