Ask Clarifying Questions First is a operations Claude Skill built by Trail of Bits. Best for: Developers and operators use this to avoid rework by validating underspecified requests before committing time to implementation..
Pause and ask targeted questions to eliminate ambiguity before implementing work.
Use this skill when a request has multiple plausible interpretations or key details (objective, scope, constraints, environment, or safety) are unclear.
Do not use this skill when the request is already clear, or when a quick, low-risk discovery read can answer the missing details.
Ask the minimum set of clarifying questions needed to avoid wrong work; do not start implementing until the must-have questions are answered (or the user explicitly approves proceeding with stated assumptions).
Treat a request as underspecified if after exploring how to perform the work, some or all of the following are not clear:
If multiple plausible interpretations exist, assume it is underspecified.
Ask 1-5 questions in the first pass. Prefer questions that eliminate whole branches of work.
Make questions easy to answer:
defaults to accept all recommended/default choices)1b 2a 3c); restate the chosen options in plain language to confirmUntil must-have answers arrive:
If the user explicitly asks you to proceed without answers:
Once you have answers, restate the requirements in 1-3 sentences (including key constraints and what success looks like), then start work.
1) Scope?
a) Minimal change (default)
b) Refactor while touching the area
c) Not sure - use default
2) Compatibility target?
a) Current project defaults (default)
b) Also support older versions: <specify>
c) Not sure - use default
Reply with: defaults (or 1a 2a)
/plugin install ask-clarifying-questions-first@trailofbitsRequires Claude Code CLI.
Developers and operators use this to avoid rework by validating underspecified requests before committing time to implementation.
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