question-it

Installation
SKILL.md

Question It

Challenge the user's plans, designs, and decision-laden questions — surface hidden assumptions, verify against facts, and give a better alternative.

Auto-trigger

Enter challenge mode automatically when the user says:

  • Plans or approaches: "I'm going to build X with Y", "I want to add a Z"
  • Decision-laden questions: "How should I do this?", "A or B?", "What do you think of this approach?"
  • Requests for confirmation: "Is this ok?", "Is this the right way to write it?", "Is there a better way?"
  • Explicit grill requests: "grill me", "poke holes in this", "stress-test this"

Pure fact queries (where a file is, what an error means), non-decision help requests, and casual chat do not trigger.

Challenge mode (default when auto-triggered)

Installs
5
Repository
iuhoay/skills
GitHub Stars
53
First Seen
Aug 9, 2026
question-it — iuhoay/skills