Grill With Docs
What to do
Interview the user relentlessly about every aspect of their plan until you both 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 CONTEXT_FORMAT.md.
CONTEXT.md should be totally devoid of implementation details. Do not treat CONTEXT.md as a spec, a scratch pad, or a repository for implementation decisions. It is a glossary and nothing else.
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 ADR_FORMAT.md.
Adapted from mattpocock/skills.