Grill with Docs

Derived from Matt Pocock's grill-with-docs (MIT, © 2026 Matt Pocock). Matt's interview discipline + docs-anchored grilling rules preserved verbatim under MIT. Additions in this repo: 3 stdlib validators (CONTEXT.md linter, ADR scanner, glossary↔code consistency check), 3 in-depth references each citing 7+ authoritative sources, cs-grill-with-docs agent, /cs:grill-with-docs command. See Wrapper additions below.

<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.

</what-to-do> <supporting-info>

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:

1. Hard to reverse — the cost of changing your mind later is meaningful
2. Surprising without context — a future reader will wonder "why did they do it this way?"
3. 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.

</supporting-info>

Wrapper Additions

The additions below are not part of Matt's upstream skill. They operationalize the upstream's rules into deterministic, stdlib-only validators that pair naturally with the interview loop.

Workflow (with wrapper tools)

1. Pre-flight (before the first question):

   • Run scripts/context_md_linter.py CONTEXT.md if a CONTEXT.md exists — confirms the glossary is well-formed before grilling against it.
   • Run scripts/adr_scanner.py docs/adr/ if docs/adr/ exists — surfaces numbering gaps, malformed ADRs, status-frontmatter inconsistencies.
   • Run scripts/glossary_code_consistency.py --context CONTEXT.md --code src/ — flags defined-but-unused terms (dead glossary) and code-only common nouns that may need definitions. Use these flags as opening grill questions.

2. During the session (Matt's rules apply):

   • One question per turn, walking depth-first.
   • When a term is sharpened: edit CONTEXT.md immediately; re-run context_md_linter.py if the edit is structural.
   • When an ADR is warranted: write it under docs/adr/; re-run adr_scanner.py to confirm numbering.

3. Closing:

   • Final glossary_code_consistency.py run to confirm no new orphan terms were introduced.
   • Summarize: terms added/re