Drill Me — Agent Skills — Robin van Baalen

When to use

Use when you have a plan, spec, ticket, RFC, design doc, or rough idea that should be stress-tested before anyone writes code. Drill Me is the opposite of yes-and brainstorming: the plan already exists, and the job is to find the unresolved forks, surface them in a sensible order, and close them. Skip it when there is no plan yet (brainstorm instead), when a single clarifying question would do, or when the change is a one-line edit.

How it works

Scans the plan for major branches — scope, users, constraints, data model, interface contracts, integration points, edge cases, non-functionals, rollout, testing, future-proofing
Explores the codebase first, answering anything the repo, tests, git log, or config already settles
Asks one opinionated question per turn, each with a recommended default, a one-sentence rationale, and a credible alternative
Walks the design tree depth-first, resolving a parent decision before drilling into its children
Stops when every material decision is closed — or when you say “enough, build it” — and says so explicitly
Outputs a resolved plan: goal, scope in/out, decisions with rationale, deferred questions, and a single concrete next step

Capabilities

Codebase before user — Greps for the auth pattern, the test framework, existing utilities, and nearby coding style rather than spending your time on questions the repo answers. It states what it found so a wrong inference can be corrected.

Calibrated intensity — 2-5 questions for a one-file change, 6-15 for a multi-file feature, 15-30+ for an architectural initiative. Trivial plans get an honest offer to skip drilling entirely.

Binary questions with defaults — “Postgres or SQLite?” beats “what database?”. Every question commits to an answer so you can confirm with “yes” instead of writing an essay. No hedging, no multi-question barrages, no restating your idea back at you.

Handoff — Offers to save the resolved plan to docs/plans/<slug>.md, and suggests handing implementation-bound work to superpowers:writing-plans.

Invoke

/drill-me:drill-me

It also fires automatically on natural phrases like “drill me”, “interview me”, “interrogate this plan”, “stress test this”, “poke holes in this”, “what am I missing”, “make sure we’re aligned”, or “before I build this…” with an idea attached.