Grill With Docs

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:

/
├── PROJECT.md
├── CONTEXT.md
├── docs/
│   └── adr/
│       ├── current/
│       │   ├── 0001-2026-01-04-0900-event-sourced-orders.md
│       │   └── 0002-2026-02-11-1030-postgres-for-write-model.md
│       └── archived/
└── src/

If a CONTEXT-MAP.md exists at the root, the repo has multiple contexts. The map points to where each one lives:

/
├── PROJECT.md
├── CONTEXT-MAP.md
├── docs/
│   └── adr/current|archived/          ← system-wide decisions
├── src/
│   ├── ordering/
│   │   ├── CONTEXT.md
│   │   └── docs/adr/current|archived/ ← context-specific decisions
│   └── billing/
│       ├── CONTEXT.md
│       └── docs/adr/current|archived/

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 PROJECT.md exists, create one when the project's purpose/direction is being pinned down (format in [PROJECT-FORMAT.md](../grill-me-code-style/_shared/PROJECT-FORMAT.md)). If no docs/adr/ exists, create docs/adr/current/ 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-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.

Capture purpose in PROJECT.md

Purpose, goals, and product direction do NOT belong in CONTEXT.md (glossary) or in ADRs (individual decisions) — they live in PROJECT.md. When the project's "why" or "where it's going" comes up — or when you notice a CONTEXT.md that has bloated into problem statements and roadmaps — capture/extract it into PROJECT.md using the format in [PROJECT-FORMAT.md](../grill-me-code-style/_shared/PROJECT-FORMAT.md), and keep CONTEXT.md a pure glossary.

This skill is the single owner of PROJECT.md — for any repo, new or existing. When purpose is thin or absent, walk the seven-part "What to ask" checklist in [PROJECT-FORMAT.md](../grill-me-code-style/_shared/PROJECT-FORMAT.md), one question at a time with a recommended default, to produce a professional PROJECT.md. Other skills (the grill-me-code-style pair) don't write their own purpose questions — they offer to run this flow and hand off here.

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](./ADR-FORMAT.md) — new ADRs go into docs/adr/current/; when one supersedes another, move the old file into docs/adr/archived/ and cross-link them.

Source & license

This open-source skill is cataloged on AgentStack and links to its original source — we do not rehost the code.

• Author: YosefHayim
• Source: YosefHayim/dufflebag
• License: MIT
• Homepage: https://www.npmjs.com/package/ys-dufflebag

Install and usage instructions live in the source repository linked above.