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Asking Questions

Teaches Claude when to stop guessing and ask a well-structured clarifying question instead.

UtilitiesBeginner★ 147⑂ 5AI score 10/10Last updated: Aug 31, 2026

What it does

Stops Claude from guessing (and building the wrong thing) when your request is ambiguous or has multiple valid implementations.

  • When to ask: multiple valid technical approaches, missing critical context (DB type, deploy target), potentially destructive requests ("clean up files" = delete or archive?), vague scope ("refactor", "optimize"), conflicting requirements
  • When not to ask: the request is already clear, the answer is inferable from codebase conventions, or the question wouldn't change the outcome
  • Question format: state what you analyzed → offer 2–5 concrete options with trade-offs → ask directly → optionally propose a sane default
  • Progressive disclosure: layer questions instead of dumping them all at once
  • After the answer: acknowledge, proceed immediately, and carry the revealed preference forward

Who it's for

  • Anyone who keeps redoing work because Claude picked an approach without checking
  • Anyone annoyed by constant low-value confirmation prompts
  • Teams standardizing how AI assistants communicate

Examples

  1. "Add error handling" → Claude offers global middleware vs. wrapper functions vs. custom error classes, each with a one-line trade-off.
  2. "Clean up the migrations" → Claude asks archive to /old-migrations or delete, warning that deletion can break databases that haven't run them.
  3. "Add real-time updates" → Claude first asks WebSockets vs. SSE vs. polling, then follows up with Socket.io vs. native only if needed.

· · · Install guide · · ·

Try it now, no install

Paste this into Claude to use the skill without installing anything.

Read the instructions in this file and follow them to help me:
https://raw.githubusercontent.com/oaustegard/claude-skills/HEAD/asking-questions/SKILL.md

What I want: (describe your task here)

If Claude can't open the link, open it yourself and paste the contents instead.

↓ If it works for you, download the ZIP below and install it. Then it runs on its own — no pasting each time.

Install in the Claude app (no terminal)
  1. Download the ZIP with the button below.
  2. In Claude, open Settings → Capabilities and turn on 'Code execution and file creation'. (one time)
  3. Go to Customize → Skills → + → 'Upload a skill' and upload the ZIP.
↓ Download ZIP
Install in Claude Code

Let Claude do it — paste this into Claude Code

Install the skill I found on Claude Skill Mart.
Copy the asking-questions folder from the GitHub repo oaustegard/claude-skills into my ~/.claude/skills/asking-questions/.
When it's done, tell me in one line what this skill can do.

Install with a command instead

git clone https://github.com/oaustegard/claude-skills.git /tmp/claude-skills && mkdir -p ~/.claude/skills && cp -r /tmp/claude-skills/asking-questions ~/.claude/skills/

⚠ This is a third-party skill. Check the source repository before installing.

  1. Open a terminal.
  2. Clone the repo: git clone https://github.com/oaustegard/claude-skills.git
  3. Create the skills directory: mkdir -p ~/.claude/skills
  4. Copy just this skill: cp -r claude-skills/asking-questions ~/.claude/skills/
  5. Verify that ~/.claude/skills/asking-questions/SKILL.md exists.
  6. Restart Claude Code and run /skills to confirm it is listed.
  7. Test it with a deliberately vague prompt such as "optimize this project" and check that Claude responds with options instead of guessing.
View source on GitHub ↗License: MIT