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ClaudSkills / General / business-ops

Drill Me

Category: General  ·  Sub-category: business-ops  ·  Last updated:
Use whenever the user has a plan, spec, RFC, ticket, design doc, or rough idea they want stress-tested before code is written. Triggers on "drill me", "interview me", "interrogate this plan", "stress test this", "what am I missing", "make sure we're aligned", "poke holes in this", "drill into this", "before I build this..." with an idea attached, or any time non-trivial work is about to start and pre-implementation alignment matters. Walks the design tree one branch at a time, asks one opinionated question per turn with a recommended answer, and explores the codebase instead of asking when the answer is already there. Continues until shared understanding is reached. Use this even when the user doesn't explicitly invoke the skill, as long as the situation matches — pre-implementation drilling is undertriggered by default.
Security AStatic scan found no risk patternsHow grading works ›

From the source SKILL.md

Interview the user relentlessly about every aspect of the plan until shared understanding is reached. Walk the design tree depth-first, resolving each decision before moving to its dependents. For every question, commit to a recommended answer with a brief rationale so the user can confirm with "yes" instead of writing an essay.

What this skill does

Drill Me is a community-contributed Claude Code skill in the business-ops sub-category. It ships as a SKILL.md file that Claude Code auto-discovers under ~/.claude/skills/drill-me/ and loads when your prompt matches the skill's trigger.

When to invoke it: Use whenever the user has a plan, spec, RFC, ticket, design doc, or rough idea they want stress-tested before code is written. Triggers on "drill me", "interview me", "interrogate this plan", "stress test this", "what am I missing", "make sure we're aligned", "poke holes in this", "drill into this", "before I build this.

Who uses this skill

The Drill Me Claude Code skill is built for Claude Code users and developers across all disciplines looking for general-purpose AI assistance. It's part of ClaudSkills (also referred to as Claude Skills or Claude Code Skills) — the open community-curated registry of 174,000+ SKILL.md files for Anthropic's Claude Code agent and the wider Claude ecosystem (Claude API, Claude Agent SDK).

How to install

Free

Manual install (2 steps)

mkdir -p ~/.claude/skills/drill-me
curl -L https://claudskills.com/skills/drill-me/SKILL.md \
  -o ~/.claude/skills/drill-me/SKILL.md

Or just download SKILL.md directly and drop it into ~/.claude/skills/drill-me/. Claude Code auto-discovers it on next session.

Skills live at ~/.claude/skills/drill-me/SKILL.md on macOS/Linux, or %USERPROFILE%\.claude\skills\drill-me\SKILL.md on Windows. See the full install guide for step-by-step instructions.

Telegram

📱 Install from your phone or desktop Telegram

Open @claudskills_bot on Telegram, tap Open Desktop App, and the desktop app installs this skill for you. Or share the bot link with a colleague — they get the same one-tap install. Learn more →

Pro

One-click install via the desktop app

The ClaudSkills desktop app installs any skill directly into ~/.claude/skills/ with one click — no terminal required. Pro starts at $9/mo or $149 lifetime.

Pro

For the full experience including quality scoring and one-click install features for each skill — upgrade to Pro.

See pricing → Download desktop app

Frequently asked questions

How do I install the Drill Me Claude Code skill?
Install via the ClaudSkills desktop app (one click) or copy SKILL.md from the source repository to ~/.claude/skills/drill-me/SKILL.md and restart Claude Code. Both flows are detailed at claudskills.com/install/.
What does the Drill Me skill do?
Use whenever the user has a plan, spec, RFC, ticket, design doc, or rough idea they want stress-tested before code is written. Triggers on "drill me", "interview me", "interrogate this plan", "stress test this", "what am I missing", "make sure we're aligned", "poke holes in this", "drill into this", "before I build this..." with an idea attached, or any time non-trivial work is about to start and pre-implementation alignment matters. Walks the design tree one branch at a time, asks one opinionated question per turn with a recommended answer, and explores the codebase instead of asking when the answer is already there. Continues until shared understanding is reached. Use this even when the user doesn't explicitly invoke the skill, as long as the situation matches — pre-implementation drilling is undertriggered by default.
Is this skill free to install?
Yes. ClaudSkills is an open registry — every skill keeps its source repository's license, and manual install via copy is free. ClaudSkills Pro ($9/mo, $79/yr, or $149 one-time) adds one-click install via the desktop app and a multi-signal Quality Score.
When should I use the Drill Me skill?
Use Drill Me when your Claude Code task falls under the General category — specifically in the business ops area. Claude Code auto-discovers installed skills and invokes the right one based on the task description, so you can also ask Claude directly (e.g. "use Drill Me" or describe the task and let Claude pick). Browse related skills at /category/general/.
What is a Claude Code skill and how does the Drill Me skill fit in?
A Claude Code skill is a SKILL.md file that lives under ~/.claude/skills/<name>/ and tells the Claude Code CLI agent how to perform a specific task (instructions, prompts, allowed tools). Skills are auto-discovered at session start. Drill Me is one of 67,000+ skills indexed in the open ClaudSkills catalog, classified under the General category. Learn more at /learn/what-is-a-claude-skill/.

Attribution & license

Cite this skill

If you reference this skill in a blog post, paper, or documentation, you can cite it as:

APA
rvanbaalen. (2026). Drill Me [Claude Code skill]. ClaudSkills. https://claudskills.com/skills/drill-me/
BibTeX
@misc{drill-me-2026,
  author    = {rvanbaalen},
  title     = {Drill Me [Claude Code skill]},
  year      = {2026},
  publisher = {ClaudSkills},
  url       = {https://claudskills.com/skills/drill-me/}
}

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Security scan

Grade A · scanned 2026-08-02 — free static scan against the OWASP Agentic Skills Top 10.

No risk patterns were found in any of the ten OWASP-aligned categories. How grading works ›

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