Grill Me

Interview the user relentlessly about a plan or design using structured Socratic questioning until reaching high confidence. Walk the decision tree systematically, uncover hidden assumptions, expose edge cases, and validate feasibility before implementation.

Workflow

Phase 1: Read Context and Scope

Before asking anything, gather the full context:

• Read any provided design documents, specs, or written plans
• Read relevant code if the user references existing systems
• Understand the scope: is this a new feature, refactor, infrastructure change, architecture shift?
• Identify the primary risk factors and dependencies

If the user hasn't provided context, ask them to share the plan first:

What's the design or plan you want me to grill you on? Please share:
- A brief description or goals
- Any relevant code or documentation
- Constraints or requirements

Do not proceed until you have context to work with.

Phase 2: Identify Question Categories

Structure your questioning around these categories:

Category	Focus	Example Questions
Requirements	What is the user trying to solve?	"What problem does this solve?" "Who are the users?" "What success looks like?"
Assumptions	What is the user taking for granted?	"Why are you using technology X?" "What if that assumption is wrong?" "Have you validated this with users?"
Constraints	What are the boundaries?	"What are the hard constraints (time, budget, scale)?" "What are you not allowed to change?" "What's the deployment path?"
Dependencies	What else must be true?	"What other systems must exist?" "What's the critical path?" "What could block you?"
Edge Cases	What could break it?	"What happens at scale?" "What about error cases?" "What if X fails?"
Validation	How will you know it works?	"How will you measure success?" "What are your test criteria?" "How will you catch regressions?"

Phase 3: Build the Decision Tree

Map out the logical dependencies between decisions:

Primary decision
├── Sub-decision A
│   ├── Implementation choice A.1
│   └── Implementation choice A.2
├── Sub-decision B
│   ├── Validation approach B.1
│   └── Rollback plan B.2
└── Sub-decision C

Identify which decisions must be resolved first (blockers) and which can be explored in parallel.

Important: Ask about high-impact, high-uncertainty decisions first. Skip decisions that are already locked down (unless you spot contradictions).

Phase 4: Ask Questions Sequentially

For each unresolved branch, ask exactly one focused question:

Structure of each question:

1. Establish context — briefly remind the user why this matters
2. Ask the question — specific, not open-ended
3. Provide your recommended answer — what you'd do or what you've seen work
4. Flag risks — what could go wrong if the opposite choice is made
5. Pause for response — wait for the user's answer before moving on

Example:

You're planning async message processing. The question is:
should messages be processed in order (FIFO) or can they be out of order?

My recommendation: enforce FIFO unless you have a specific reason not to.
Out-of-order processing complicates debugging and introduces race conditions.

Risk if you go out-of-order: state consistency bugs that are hard to reproduce.

What's your thinking here?

Phase 5: Explore the Codebase When Applicable

If a question can be answered by reading code, do that instead of asking:

# Examples:
grep -r "MessageQueue" src/          # How are messages currently queued?
grep -r "error handling" src/        # What error patterns already exist?
find . -name "*.test.ts" | head -5   # What's the testing pattern?

Surface findings to the user:

I found that your existing API already has retry logic in [file:line].
Given that, my question becomes: should we reuse this pattern or replace it?

Phase 6: Escalate on Conflicts

If the user's answer contradicts earlier statements or introduces new risks, surface this explicitly:

You said earlier that latency is critical, but now you're proposing a
synchronous validation step that could block for seconds.
How do you reconcile these constraints?

Do not accept contradictions silently. Push back gently but clearly.

Phase 7: Recognize Completion Signals

Stop questioning when:

• All high-impact decisions are resolved — the user has clear answers to every critical question
• All branches of the decision tree are explored — you've walked the full dependency graph
• Validation plan is solid — the user knows how to measure success and catch failures
• Risk mitigation is addressed — for each major risk, there's a mitigation or acceptance
• The user signals confidence — they say "I'm confident now" or "This is locked"
• You've reached a decision impasse — the user is unwilling to change their mind despite contradictions (note this in your closing)

Phase 8: Summarize and Confirm

When you've finished questioning, provide a brief summary:

## Summary

### Decisions Locked
- Message processing: FIFO with retry logic (max 3 retries)
- Deployment: Blue-green with health checks
- Monitoring: Custom metrics on latency percentiles

### Remaining Risks
- Database scaling: you identified this but haven't validated with ops yet
- Failover time: depends on network convergence (currently untested)

### Next Steps
1. Validate with ops team on database capacity
2. Run failover simulation to measure real time
3. Build monitoring dashboard before launch

Confidence level: High on architecture, Medium on operational readiness.
Ready to design in detail?

Question Categories Reference

Requirements Questions

• "Who are the end users of this feature?"
• "What's the primary problem this solves?"
• "What's the definition of success?"
• "What's the deadline, and is it flexible?"
• "What's the budget or resource constraint?"

Assumptions Questions

• "Why did you choose technology/pattern X?"
• "What are you assuming about user behavior?"
• "What if that assumption is wrong?"
• "Have you validated this with real users/data?"
• "Are there alternatives you considered and rejected?"

Constraints Questions

• "What can't you change about the existing system?"
• "What are the hard limits (performance, cost, security)?"
• "What dependencies do you have on other teams?"
• "What's your deployment window?"
• "What's the rollback plan if things go wrong?"

Dependencies Questions

• "What has to be true for this to work?"
• "What systems must integrate with yours?"
• "What's the critical path?"
• "What could cause cascading failures?"
• "How do you handle partial failures?"

Edge Cases Questions

• "What happens when X fails?"
• "How do you handle malformed input?"
• "What's your load limit, and what happens beyond it?"
• "How do you prevent race conditions?"
• "What about old API clients or legacy data?"

Validation Questions

• "How will you know this is working?"
• "What metrics matter most?"
• "How will you catch regressions?"
• "What's your monitoring strategy?"
• "What's your testing approach—unit, integration, e2e, load?"

Examples

Positive Trigger

User: "Grill me on this auth system design."

Expected behavior: Read the design, identify key decisions, ask probing questions about assumptions and edge cases, validate feasibility, and push back on contradictions.

---

User: "Stress-test my plan for migrating to a new database."

Expected behavior: Map out the migration steps, probe assumptions about downtime and rollback, identify risks around data consistency, ask validation questions.

---

User: "Interview me on this feature proposal before I write code."

Expected behavior: Understand the requirements, validate the approach against constraints, uncover hidden dependencies, ensure the user is thinking through edge cases.

Non-Trigger

User: "Review this code and fix the bugs."

Expected behavior: Do not use grill-me. The user wants code review and fixes, not an interview. Use a code review skill instead.

---

User: "What do you think of this design?"

Expected behavior: Do not use grill-me unless the user explicitly asks to be grilled. Provide direct feedback or a review instead.

Troubleshooting

Skill Does Not Trigger

• Error: Claude gives feedback or suggestions instead of asking questions.
• Cause: User said "review" or "give feedback" instead of "grill me" or "stress-test".
• Solution: Explicitly ask to be grilled: "Grill me on this plan", "Stress-test my design", "Interview me about this architecture".

Questions Feel Generic or Repetitive

• Error: Questions don't reflect the specific plan or codebase context.
• Cause: Insufficient context provided, or questions asked too quickly before analysis.
• Solution: Share the plan, design doc, or code first. Spend Phase 1 understanding the context thoroughly before asking.

User Feels Defensive

• Error: User pushes back on the questioning style or says "I know this already".
• Cause: Questions felt accusatory or didn't acknowledge the user's expertise.
• Solution: Reframe as collaborative: "Let me make sure I understand your thinking..." instead of "Have you considered...?"

No Clear Direction Emerges

• Error: After many questions, the plan is still unclear or contradictory.
• Cause: Too many parallel branches explored at once, or user is uncertain about goals.
• Solution: Zoom out. Ask: "What's the ONE most important constraint for this design?" and rebuild the decision tree from there.