Setup & Installation
npx skills add https://github.com/trailofbits/skills --skill ask-questions-if-underspecified
https://github.com/trailofbits/skills/tree/main/plugins/ask-questions-if-underspecified
View on GitHubWhat This Skill Does
Guides an AI agent to pause and ask clarifying questions when a request has ambiguous objectives, unclear scope, or missing constraints. The agent asks 1-5 targeted questions before doing any work, offers multiple-choice options with defaults, and waits for answers before proceeding.
Without this skill, agents make plausible-but-wrong assumptions and produce work that must be thrown out; structured upfront questions eliminate entire branches of wasted effort.
When to use it
- Asking about target file scope before a refactor that could touch dozens of files
- Getting confirmation on compatibility requirements before upgrading a dependency
- Clarifying acceptance criteria before writing tests for an underspecified feature
- Resolving ambiguous rollback requirements before running a data migration
- Confirming which components are in-scope before a performance optimization pass