ryan-brosas Grill Me
When to Use
You have a plan, spec, ADR, or architecture that you want to stress-test before committing to implementation. You want someone to find the holes.
Core Principle
A plan that survives a good grilling is a plan worth implementing. A plan that falls apart under questions would have fallen apart during implementation, costing more.
Workflow
Ask one question at a time; let the person answer fully before asking another. Walk the Common Targets as needed. Stop when the grillee has a concrete, specific answer to each question, or when the questions are repeating (same shape, different topic).
How to Grill
Ask:
- "What assumptions are you making that could be wrong?"
- "What's the most likely thing to fail?"
- "What if X is 10x larger / smaller / slower?"
- "What's the cost of being wrong?"
- "What's the simplest way to test this?"
- "What's the hardest part? Why?"
- "What's the rollback plan?"
- "What would make this a mistake?"
- "Who disagrees with this? Why?"
- "What's the non-goal everyone forgets?"
- "What are we not talking about?"
One question at a time. Let the person answer fully before asking another.
What a Good Grilling Looks Like
- Questions surface assumptions, not opinions.
- The griller is curious, not confrontational.
- The grillee answers in "I think" and "I'm assuming", not "it's obvious".
- After 10-15 questions, the plan is either stronger or abandoned.
- The griller doesn't need to "win", they need to find the hole.
Common Targets
| Target | Question |
|---|---|
| Cost estimate | "What if it takes 3x as long?" |
| Scale estimate | "What if traffic grows 10x this month?" |
| One-vendor risk | "What if vendor shuts down?" |
| "Just use X" | "What does X not do?" |
| "We'll iterate" | "What's the first working version look like?" |
| "It's simple" | "Define simple. How many moving parts?" |
| "Everyone agrees" | "Who did you not ask?" |
| "No dependencies" | "What do you depend on that you don't control?" |
When to Stop Grilling
Stop when the grillee has a concrete, specific answer to each question, not "I'll figure it out later." Stop when the questions are repeating (same shape, different topic).
Common Mistakes
Asking 5 questions in one message; grilling from a position of "I know better" (stifles ideas); stopping too early (first two questions are easy); stopping too late (grilling the trivial parts); not documenting the answers; "grilling as attack" (destroys trust, not plans).
Red Flags
No assumptions stated. "I'll figure it out later" as a crutch. "everyone agrees" without asking everyone. cost estimate without a range. "it's simple" without definition. no rollback plan. "we'll iterate" before v1 is defined. "no dependencies" without checking. vulnerability mentioned, dismissed. "I'm not worried about X" (X is the thing to worry about).
Anti-Patterns
5 questions at once; "I know better" (stifles); stop too early (first 2 are easy); grill the trivial; no doc; attack mode.
Verification
After 10–15 questions, the plan is either stronger or abandoned, and the answers are documented, not left in chat.
References
N/A, no reference files; the question banks and targets are inline in this skill.