Ask Questions When Underspecified

VerifiedSafe

Ask minimum clarifying questions before implementing to avoid wrong work. Only use when explicitly invoked.

Sby Skills Guide Bot
DevelopmentIntermediate
207/23/2026
Claude CodeCursorWindsurfCopilotCodex
#requirements-clarification#underspecified-requests#specification#ai-agent-practices

Recommended for

Our review

This skill enables an AI agent to ask clarifying questions before executing an ambiguous request to avoid incorrect work.

Strengths

  • Reduces misinterpretation errors by soliciting essential details.
  • Provides structured, compact options for easy user responses.
  • Handles assumptions explicitly when the user wants to proceed without full answers.
  • Saves time by eliminating unnecessary work branches through targeted questions.

Limitations

  • May slow down initiation if questions are not well prioritized.
  • Not suitable for trivial tasks where clarification is unnecessary.
  • Relies on the user's ability to provide precise answers.
When to use it

Best for complex, ambiguous, or multi-interpretation requests given to an AI agent.

When not to use it

Avoid for simple, well-defined, or urgent tasks where clarification would cause unnecessary delay.

Security analysis

Safe
Quality score88/100

The skill only provides conversational guidance for clarifying requirements; it contains no instructions to execute commands, access external resources, or perform any destructive or risky operations.

No concerns found

Examples

Implement user authentication
Implement user authentication for my web app.
Add search feature
Add a search feature to the API.
Refactor database module
Refactor the database module to improve performance.

Skill file:


name: ask-questions-if-underspecified description: Clarify requirements before implementing. Do not use automatically, only when invoked explicitly.

Ask Questions If Underspecified

Goal

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).

Workflow

1) Decide whether the request is underspecified

Treat a request as underspecified if after exploring how to perform the work, some or all of the following are not clear:

  • Define the objective (what should change vs stay the same)
  • Define "done" (acceptance criteria, examples, edge cases)
  • Define scope (which files/components/users are in/out)
  • Define constraints (compatibility, performance, style, deps, time)
  • Identify environment (language/runtime versions, OS, build/test runner)
  • Clarify safety/reversibility (data migration, rollout/rollback, risk)

If multiple plausible interpretations exist, assume it is underspecified.

2) Ask must-have questions first (keep it small)

Ask 1-5 questions in the first pass. Prefer questions that eliminate whole branches of work.

Make questions easy to answer:

  • Optimize for scannability (short, numbered questions; avoid paragraphs)
  • Offer multiple-choice options when possible
  • Suggest reasonable defaults when appropriate (mark them clearly as the default/recommended choice; **bold the recommended choice in the list, or if you present options in a code block, put a bold "Recommended" line immediately above the block and also tag defaults inside the block)
  • Include a fast-path response (e.g., reply defaults to accept all recommended/default choices)
  • Include a low-friction "not sure" option when helpful (e.g., "Not sure - use default")
  • Separate "Need to know" from "Nice to know" if that reduces friction
  • Structure options so the user can respond with compact decisions (e.g., 1b 2a 3c); restate the chosen options in plain language to confirm

3) Pause before acting

Until must-have answers arrive:

  • Do not run commands, edit files, or produce a detailed plan that depends on unknowns
  • Do perform a clearly labeled, low-risk discovery step only if it does not commit you to a direction (e.g., inspect repo structure, read relevant config files)

If the user explicitly asks you to proceed without answers:

  • State your assumptions as a short numbered list
  • Ask for confirmation; proceed only after they confirm or correct them

4) Confirm interpretation, then proceed

Once you have answers, restate the requirements in 1-3 sentences (including key constraints and what success looks like), then start work.

Question templates

  • "Before I start, I need: (1) ..., (2) ..., (3) .... If you don't care about (2), I will assume ...."
  • "Which of these should it be? A) ... B) ... C) ... (pick one)"
  • "What would you consider 'done'? For example: ..."
  • "Any constraints I must follow (versions, performance, style, deps)? If none, I will target the existing project defaults."
  • Use numbered questions with lettered options and a clear reply format
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)

Anti-patterns

  • Don't ask questions you can answer with a quick, low-risk discovery read (e.g., configs, existing patterns, docs).
  • Don't ask open-ended questions if a tight multiple-choice or yes/no would eliminate ambiguity faster
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