grill-me

Grill me

Use this skill to relentlessly interrogate a plan or design until every branch of the decision tree is resolved. Pure interrogation is the default. Switch to the explicit documentation mode only when the user signals domain-document intent by mentioning CONTEXT.md, ADRs, or a domain glossary; never create those files silently.

Use this skill when

• The user wants to be grilled, stress-tested, or interviewed about a plan or design.
• The user explicitly says "grill me" and does not mention domain docs, CONTEXT.md, or ADRs.
• The user asks to grill a plan while explicitly asking to create or update CONTEXT.md, ADRs, or a domain glossary.
• The user wants to think through a decision tree before committing to a direction.

Do not use this skill when

• The request is under-specified and needs sharpening before interrogation — route to reverse-prompt.
• A completed plan needs formal reviewer-gated, multi-round approval — route to plan-review.
• The user wants standalone documentation (README, guide, or runbook) — route to doc-coauthoring.

Routing boundary

Situation	Use this skill?	Route instead
User says "grill me" about a plan with no documentation intent	Yes	-
User says "grill me" and mentions CONTEXT.md, ADRs, or a domain glossary	Yes — documentation mode	-
User's request is too vague to interrogate	No	reverse-prompt
Completed plan needs Jason/Freddy or other reviewer-gated rounds	No	plan-review

Inputs to gather

Required before starting

• The plan, design, or decision the user wants stress-tested.

Helpful if present

• Prior conversation context about the feature.
• The repository codebase for verification of claims.

Only investigate if encountered

• An existing CONTEXT.md, CONTEXT-MAP.md, or docs/adr/ directory when the user explicitly asks for documentation mode.

First move

1. Read the plan or design the user has presented.
2. If documentation mode was explicitly requested, check for existing CONTEXT.md/CONTEXT-MAP.md and docs/adr/; otherwise do not look for or create documentation artifacts.
3. Identify the first unresolved decision branch and ask one question, providing your recommended answer using the available user-input mechanism.

Workflow

1. Ask one question at a time. Walk down each branch of the design tree, resolving dependencies between decisions sequentially; provide your recommended answer with every question.
2. Explore instead of asking when a question can be answered by examining the codebase.
3. In documentation mode, challenge terms against the existing glossary, sharpen fuzzy domain language, and cross-reference claims with code.
4. In documentation mode, update CONTEXT.md inline only after the user has explicitly requested that mode and a domain term is resolved; offer ADRs only for hard-to-reverse, surprising trade-offs.
5. Repeat until all branches are resolved and the user confirms shared understanding.

Outputs

• A shared understanding of the plan or design, with all decision branches resolved.
• In documentation mode only: updated or newly created CONTEXT.md and zero or more qualifying ADRs.

Guardrails

• Ask questions one at a time; never dump a wall of questions.
• Provide a recommended answer with every question.
• Explore the codebase when it can answer a question; do not ask the user what the code already tells you.
• Keep pure interrogation free of documentation side effects.
• Never create or update CONTEXT.md, CONTEXT-MAP.md, or ADRs unless the user explicitly signals documentation mode.
• In documentation mode, define only project-specific domain terms in CONTEXT.md, one sentence each, and use the formats in the reference files.

Validation

• Confirm the skill activates on "grill me" prompts without domain-doc intent.
• Confirm the same trigger enters documentation mode when the user mentions CONTEXT.md, ADRs, or a domain glossary.
• Confirm vague requests route to reverse-prompt and reviewer-gated plan approval routes to plan-review.
• Run node skills/skill-creator/scripts/validate-skill-library.mjs skills/grill-me/SKILL.md.
• Smoke test:
  • should trigger: "Grill me on my plan to refactor the notification service."
  • should trigger in documentation mode: "Grill me and build CONTEXT.md as we go."
  • should not trigger: "Sharpen this vague request before I start." (→ reverse-prompt)

Examples

• "Grill me on this plan to split the monolith into two services."
• "Stress-test my caching design before I commit to it."
• "Grill me on order cancellation and update CONTEXT.md as we resolve domain terms."

Reference files

• references/interrogation-patterns.md — lightweight question sequencing and completion guidance.
• references/session-playbook.md — scenario construction, contradiction surfacing, fuzzy-term resolution, and explicit documentation-mode patterns.
• references/context-format.md — CONTEXT.md format when documentation mode is explicitly requested.
• references/adr-format.md — ADR format and offering criteria for qualifying decisions.
• assets/context-template.md — starter template for a new CONTEXT.md, used only in documentation mode after the user requests it.