The “grill me” skill that pressure-tests any plan

Here’s a real one to start the swipe file. This is a Claude skill — a SKILL.md file that turns Claude from “answer machine” into something that interviews you about your plan before any work happens. Instead of agreeing with you, it walks down every branch of a decision and makes you defend each one, one question at a time.

It’s how this very site got designed. Worth having in your back pocket for any plan that feels half-baked.

How to use it

Point Claude at the skill and describe what you’re planning. It’ll ask you one sharp question at a time — and crucially, recommend an answer each time — instead of dumping a checklist on you. You answer; it digs deeper or moves on. It also captures decisions as you make them, so you finish with a written record, not just a conversation.

The source

It’s open source, by Matt Pocock:

https://github.com/mattpocock/skills/blob/main/skills/engineering/grill-with-docs/SKILL.md

More swipe-file entries coming (Braden): drop your real prompts, templates, and the actual skills/MCP setups you use here — one MDX file each, section: "swipe-file". The bar is “copy, paste, go.” Prioritize the ones people normally pay for.