Grilling Skill: Design-Tree Interviews for Plan Stress-Tests

Tue, 18 Aug 2026 00:00:00 +0000

Saying “challenge my plan” to an AI usually gets you three vague questions and a compliment. Matt Pocock built the Grilling skill to fix exactly that: it runs a structured interview where every question has a recommended answer and nothing is left silently assumed. It ranks #60 on the skills.sh all-time leaderboard with 448,900 installs, and it sits underneath grill-me and grill-with-docs — the two skills people actually type. I pulled the skill files and their long-form docs out of the mattpocock/skills repo (221K stars) and read every line, because the README calls it a “primitive” and skips the details that decide whether it works for you.

Grilling Skill on Top AI Skills

Grilling Skill: Design-Tree Interviews for Plan Stress-Tests