Grill Me

Grill Me

Purpose

Stress-test a plan, design, or idea through relentless Socratic questioning. Walk down every branch of the decision tree, resolve dependencies between decisions one-by-one, and reach a shared understanding where no assumption is left unchallenged.

When to Use

Trigger ONLY when the user explicitly uses the word "grill" — e.g.:

• "grill me on this"
• "grill me on my plan / architecture / design"
• "I want you to grill me before I present"
• PT: "me grille sobre esse plano"

Do NOT trigger for synonyms or near-misses, even when the intent seems similar:

• "stress-test this" → not grill-me
• "poke holes in my plan" → not grill-me
• "play devil's advocate" → not grill-me
• "challenge my assumptions" → not grill-me
• "pressure-test this" → not grill-me
• "review this and tell me what's wrong" → not grill-me
• "give me feedback" → not grill-me

Workflow

Step 0 — Understand the Subject

Read the plan, design, or idea the user has provided. If working in a codebase, explore relevant files before asking questions that can be answered by reading the code.

Step 1 — Build the Decision Tree (silent)

Before asking the first question, mentally map:

• Core decisions already made (what's locked in)
• Branches that are open or unresolved
• Dependencies between decisions
• Unstated assumptions worth surfacing

Step 2 — Interview Relentlessly

Ask one question at a time. For each question:

1. Ask the question
2. Provide your recommended answer with brief reasoning
3. Wait for the user's response before moving on

Work through branches systematically — exhaust one thread before opening another. When an answer reveals a new sub-question, follow it immediately.

Question types to cycle through:

• Scope: What's in? What's explicitly out?
• Dependencies: What does this depend on that isn't defined yet?
• Failure modes: What breaks first under load / edge cases / bad inputs?
• Alternatives rejected: Why this approach and not X?
• Success criteria: How will you know this worked?
• Reversibility: What's hard to undo? What's the rollback plan?
• Ownership: Who owns each part when something goes wrong?

Step 3 — Resolve and Close

When all branches of the decision tree are resolved, summarize:

• Decisions confirmed
• Decisions changed or refined
• Open questions that remain (if any)
• Risks surfaced that need a mitigation plan

Critical Rules

• NEVER ask more than one question per turn
• ALWAYS provide your recommended answer alongside the question
• If a question can be answered by exploring the codebase, explore it instead of asking
• Follow threads to completion before opening new ones
• Push back on weak reasoning — don't accept "it should be fine" as an answer
• Surface assumptions the user didn't state but is implicitly relying on

Example Usage

1. "Grill me on my microservices migration plan"
2. "I want to stress-test this database schema before we build on it — grill me"
3. "We're about to kick off this project. Grill me on the architecture."
4. "I have a go-to-market plan. Pick it apart."
5. "Grill me on this carve-out strategy before I write the plan"