When to use
- A direction has been picked (post-
investigateor post-feature-doc) and you want to pressure-test it against the existing model. - Mid-
improve-codebase-architecture— the grilling loop borrows this skill's discipline.
When to skip
- The direction is still being explored — use
investigateinstead. - The plan is fully exploratory and no decisions are being committed — also
investigate. - The decision is trivially reversible — there's nothing to stress-test.
- Greenfield repo with no
CONTEXT.md/ ADRs yet → runbootstrapfirst.
What to do
Interview me relentlessly about every aspect of this plan until we reach a shared understanding. Walk down each branch of the design tree, resolving dependencies between decisions one-by-one. For each question, provide your recommended answer.
Ask the questions one at a time, waiting for feedback on each question before continuing.
If a question can be answered by exploring the codebase, explore the codebase instead.
Domain awareness
During codebase exploration, also look for existing documentation:
File structure
Most repos have a single context:
/
├── CONTEXT.md
├── docs/
│ └── adr/
│ ├── 0001-event-sourced-orders.md
│ └── 0002-postgres-for-write-model.md
└── src/
If a CONTEXT-MAP.md exists at the root, the repo has multiple contexts. The map points to where each one lives:
/
├── CONTEXT-MAP.md
├── docs/
│ └── adr/ ← system-wide decisions
├── src/
│ ├── ordering/
│ │ ├── CONTEXT.md
│ │ └── docs/adr/ ← context-specific decisions
│ └── billing/
│ ├── CONTEXT.md
│ └── docs/adr/
Create files lazily — only when you have something to write. If no CONTEXT.md exists, create one when the first term is resolved. If no docs/adr/ exists, create it when the first ADR is needed.
During the session
Challenge against the glossary
When the user uses a term that conflicts with the existing language in CONTEXT.md, call it out immediately. "Your glossary defines 'cancellation' as X, but you seem to mean Y — which is it?"
Sharpen fuzzy language
When the user uses vague or overloaded terms, propose a precise canonical term. "You're saying 'account' — do you mean the Customer or the User? Those are different things."
Discuss concrete scenarios
When domain relationships are being discussed, stress-test them with specific scenarios. Invent scenarios that probe edge cases and force the user to be precise about the boundaries between concepts.
Cross-reference with code
When the user states how something works, check whether the code agrees. If you find a contradiction, surface it: "Your code cancels entire Orders, but you just said partial cancellation is possible — which is right?"
Update CONTEXT.md inline
When a term is resolved, update CONTEXT.md right there. Don't batch these up — capture them as they happen. Use the format in ../formats/CONTEXT-FORMAT.md.
Don't couple CONTEXT.md to implementation details. Only include terms that are meaningful to domain experts.
Offer ADRs sparingly
Only offer to create an ADR when all three are true:
- Hard to reverse — the cost of changing your mind later is meaningful
- Surprising without context — a future reader will wonder "why did they do it this way?"
- The result of a real trade-off — there were genuine alternatives and you picked one for specific reasons
If any of the three is missing, skip the ADR. Use the format in ../formats/ADR-FORMAT.md.
Pairing with other skills
investigate— runs before when direction is unclear. Once a direction is chosen, hand off here.DOC-DRIFT-AUDIT.md— the terminology/ADR audit (formerly thesync-checkskill) escalates here when it finds a terminology collision or ADR contradiction in existing code.feature-doc— runs before when a feature doc is the input to grilling, or after when grilling refines the plan into a feature doc.system-design— defers here for hard-to-reverse topology decisions.improve-codebase-architecture— borrows this skill's grilling discipline in its own grilling loop.tdd-rounds— escalates here mid-round when an ADR is wobbling.
Done when
- No open questions remain on the chosen plan.
- Every term used during the session has been resolved into
CONTEXT.md(or explicitly flagged as ambiguous). - Any decision that meets all three ADR criteria has been offered (and either accepted or declined).
- The user explicitly says "this is enough" or "let's move on" — don't keep grilling past their patience.