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-docsagent,/cs:grill-with-docscommand. See Wrapper additions below.
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.
During codebase exploration, also look for existing documentation:
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.
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?"
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."
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.
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?"
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.
Only offer to create an ADR when all three are true:
If any of the three is missing, skip the ADR. Use the format in ADR-FORMAT.md.
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.
Pre-flight (before the first question):
scripts/context_md_linter.py CONTEXT.md if a CONTEXT.md exists — confirms the glossary is well-formed before grilling against it.scripts/adr_scanner.py docs/adr/ if docs/adr/ exists — surfaces numbering gaps, malformed ADRs, status-frontmatter inconsistencies.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.During the session (Matt's rules apply):
CONTEXT.md immediately; re-run context_md_linter.py if the edit is structural.docs/adr/; re-run adr_scanner.py to confirm numbering.Closing:
glossary_code_consistency.py run to confirm no new orphan terms were introduced.| Tool | One-line role |
|---|---|
scripts/context_md_linter.py |
Validate CONTEXT.md against the CONTEXT-FORMAT.md structure. PASS/WARN/FAIL per rule. |
scripts/adr_scanner.py |
Walk docs/adr/, check NNNN-slug.md pattern, numbering integrity, body completeness. |
scripts/glossary_code_consistency.py |
Cross-reference bold terms in CONTEXT.md against codebase usage. Flag dead glossary + code-only common nouns. |
references/ubiquitous_language.md — why a glossary belongs in source control (Evans, Vernon, Khononov, Wlaschin, Brandolini, Avram & Marinescu, Fowler)references/adr_practice.md — when an ADR earns its keep (Nygard, Tyree & Akerman, Zimmermann Y-statements, MADR, ThoughtWorks Radar, adr-tools, Backstage)references/context_md_as_artifact.md — CONTEXT.md as living artifact (Khononov on language drift, Kernighan on naming, BoundedContext bliki, Confluent on data contracts, Brandolini on EventStorming glossary)cs-grill-with-docs (see ../../agents/cs-grill-with-docs.md)/cs:grill-with-docs (see ../../commands/cs-grill-with-docs.md)Version: 1.0.0 Derived: Matt Pocock's grill-with-docs (MIT) + this repo's wrapper