Grill With Docs

Interview Andy relentlessly about every aspect of this plan until you 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 before continuing.

If a question can be answered by exploring the codebase, explore the codebase instead.

When to use

Triggers: grill me on this plan, stress-test the design, challenge my approach, walk the design tree, make sure we agree on the model.

Use this skill for code/architecture plans where alignment with project vocabulary matters. For looser, non-code "is this idea worth doing" sessions, use the brainstorm skill instead — that one delegates to the brainstormer specialist and saves to 00 - Chats/brainstorms/.

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:

/
├── 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 Andy uses a term that conflicts with 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 he 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 precision about the boundaries between concepts.

Cross-reference with code

When he 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 — capture as it happens.

CONTEXT.md format (compressed):

# <Project> Domain Glossary

## <Term>
One-sentence definition in the user's language. Then a paragraph for edge cases, neighbours, and what this is NOT.

## <Next term>
...

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:

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.

ADR format (compressed):

# ADR-<NNNN>: <Title>

**Status.** Accepted | Superseded by ADR-<n> | Rejected

**Context.** What were we trying to solve?

**Decision.** What did we choose?

**Consequences.** What did we trade off?

**Alternatives considered.** Briefly — what we ruled out and why.

Source

Imported from mattpocock/skills — 05-21-26. Helper files (CONTEXT-FORMAT.md, ADR-FORMAT.md, DOMAIN-AWARENESS.md) summarised inline.

Integrates with

• 03 - Skills & Rules/Agents/Specialists/brainstormer.md — non-code analog (vault-side ideation)
• 03 - Skills & Rules/Skills/to-prd.md — typical downstream once the design is grilled clean
• 03 - Skills & Rules/Skills/improve-codebase-architecture.md — shares the same grilling loop in step 3
• 03 - Skills & Rules/Rules/style-no-sycophancy.md — must be on for grilling to work

Relationship to brainstormer specialist

The brainstorm skill (Writer dept) handles "is this idea worth doing" — wide, conceptual, often outside code. grill-with-docs handles "is this design consistent with the code we have" — narrow, code-grounded, ends with CONTEXT.md and ADR updates. Different tools, no overlap.