ask-questions-if-underspecified/.skillshare-meta.json

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+{
+  "source": "github.com/trailofbits/skills/tree/main/plugins/ask-questions-if-underspecified/skills/ask-questions-if-underspecified",
+  "type": "github-subdir",
+  "installed_at": "2026-01-30T02:23:15.701719296Z",
+  "repo_url": "https://github.com/trailofbits/skills.git",
+  "subdir": "plugins/ask-questions-if-underspecified/skills/ask-questions-if-underspecified",
+  "version": "650f6e3"
+}

ask-questions-if-underspecified/SKILL.md

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+---
+name: ask-questions-if-underspecified
+description: Clarify requirements before implementing. Use when serious doubts arise.
+---
+
+# Ask Questions If Underspecified
+
+## When to Use
+
+Use this skill when a request has multiple plausible interpretations or key details (objective, scope, constraints, environment, or safety) are unclear.
+
+## When NOT to Use
+
+Do not use this skill when the request is already clear, or when a quick, low-risk discovery read can answer the missing details.
+
+## 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
+
+```text
+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.