challenge
Socratic questioning — challenge the user's assumptions and thinking before they commit.
Skill by timander
Chalk Labs
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Install
Works with Claude Code, Claude apps, Codex, Cursor, Gemini CLI, GitHub Copilot, VS Code, OpenCode, Goose, Windsurf. Read the repository before you give any tool access to your data.
npx agentmarket install skill/timander-challenge
Asks which of your tools to add it to (Claude Code, Codex, Cursor, VS Code, Windsurf, Gemini CLI, Claude Desktop) and shows the change first. See https://agentmart.dev/cli.
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About
Reviews
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Permissions
What this skill can do and what it asks for, from its SKILL.md. Checked Oct 25, 2026.
- Tools
- No tools found
- Secrets
- None asked for
- Install scripts
- None found
Network hosts it talks to 1
codeload.github.com· found in install command
Files it touches
~/.claude/skills/challenge
What's inside
- Skill name
challenge- Description
- Socratic questioning — challenge the user's assumptions and thinking before they commit. Use when the user is about to make a decision they want stress-tested.
- License
- MIT
- Instructions
- 38 lines in SKILL.md · view on GitHub
Files (1)
- SKILL.md
SKILL.md (first lines)
# Challenge My Thinking The user is about to make a decision or take an approach. Help them stress-test it. ## Questions to Ask ### Clarify the Goal - What problem are you actually solving? - How will you know when it's solved? - What does success look like? Can you give a concrete example? ### Challenge Assumptions - What are you assuming that might not be true? - What evidence supports your approach? - What would change your mind? ### Explore Alternatives - What other approaches did you consider? - What's the simplest thing that could possibly work? - What would you do if you had half the time? Double the time? ### Identify Risks - What could go wrong? - What's the worst case if this approach fails? - Is this reversible? What's the cost of being wrong? ### Surface Trade-offs - What are you optimizing for? - What are you giving up to get that? - Is that the right trade-off for this situation? --- Don't give answers. Help find better questions. What decision or approach should we examine?
From timander/copilot-instructions-starter-kit, MIT.
More from timander/copilot-instructions-starter-kit
- 0.474score
audience
timander
Switch the explanation level (learning / working / expert) for a stack mid-session.
SkillCFreshness: CClaude Code +9 - 0.474score
code-quality
timander
Offer to add opt-in lint, static-analysis, and coverage tooling for the project's language.
SkillCFreshness: CClaude Code +9 - 0.474score
diagnose
timander
One-shot systematic diagnosis script — understand the problem before suggesting fixes.
SkillCFreshness: CClaude Code +9 - 0.474score
expert-panel
timander
Simulate a panel of named experts (Fowler, Beck, Bloch, Metz, Feathers, etc.) discussing the code or design decision.
SkillCFreshness: CClaude Code +9 - 0.474score
kit-doctor
timander
Self-audit this Copilot kit for token cost, bloat, schema drift, and coverage gaps.
SkillCFreshness: CClaude Code +9 - 0.474score
options
timander
Present a decision as a set of options with trade-offs spelled out, so the user can pick well.
SkillCFreshness: CClaude Code +9 - 0.474score
refactor
timander
Apply the refactoring catalog (Fowler, Beck Tidy First, Feathers legacy techniques) to existing code.
SkillCFreshness: CClaude Code +9 - 0.474score
review
timander
Review code or a PR diff for correctness, design, smells, and missing tests.
SkillCFreshness: CClaude Code +9 - 0.474score
tdd
timander
Walk through Red-Green-Refactor explicitly for implementing a feature.
SkillCFreshness: CClaude Code +9
Signals
- Stars
- 0
- Forks
- 0
- Open issues
- 0
- Last commit (this folder)
- Jun 12, 2026 (4 months ago)
- Last release
- Jun 12, 2026 (4 months ago)
From GitHub (fetched Oct 24, 2026).
Details
- License
- MIT
- First seen
- Oct 24, 2026
- Last checked
- Oct 24, 2026
- Source
- GitHubgithub-graphql
More from timander
- 0.474score
audience
timander
Switch the explanation level (learning / working / expert) for a stack mid-session.
SkillCFreshness: CClaude Code +9 - 0.474score
code-quality
timander
Offer to add opt-in lint, static-analysis, and coverage tooling for the project's language.
SkillCFreshness: CClaude Code +9 - 0.474score
diagnose
timander
One-shot systematic diagnosis script — understand the problem before suggesting fixes.
SkillCFreshness: CClaude Code +9 - 0.474score
expert-panel
timander
Simulate a panel of named experts (Fowler, Beck, Bloch, Metz, Feathers, etc.) discussing the code or design decision.
SkillCFreshness: CClaude Code +9 - 0.474score
kit-doctor
timander
Self-audit this Copilot kit for token cost, bloat, schema drift, and coverage gaps.
SkillCFreshness: CClaude Code +9 - 0.474score
options
timander
Present a decision as a set of options with trade-offs spelled out, so the user can pick well.
SkillCFreshness: CClaude Code +9
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challenge skill. Agent Mart. https://agentmart.dev/skills/timander-challenge (last updated 2026-10-24)