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LEARN.EXE — AI SKILLS 101

If you use Claude, ChatGPT, or Cursor and find yourself re-explaining your context every session — this is for you.

What is an
AI Skill?

A file that tells Claude how to think like you. Instead of re-explaining your context every session, your skill does it automatically.

THE PROBLEM — GENERIC AI OUTPUT

WITHOUT A SKILL

You open Claude and type: “Help me write a PRD for our new payments feature.”

Claude gives you a generic template. It doesn’t know you work in fintech. It doesn’t know your team uses ICE scoring. It doesn’t know your VP wants executive summaries first.

So you spend 10 minutes adding context. Again. Every. Single. Time.

WITH A SKILL

You type the same prompt. But Claude already knows:

  • You’re a Senior PM in consumer fintech
  • You use ICE scoring weighted by regulatory risk
  • PRDs should lead with the user problem
  • Exec summaries first, details below the fold
  • Two-way door decisions: ship this week, iterate

The output is calibrated. It sounds like you wrote it. No re-prompting needed.

ANATOMY OF A SKILL.MD — 4 SECTIONS
01

Role & Context

Who you are and where you operate. Your title, domain, team size, industry constraints. This grounds every response in your reality, not generic advice.

# Senior PM — Consumer Fintech
Use this skill when working on consumer fintech product
decisions, PRD authoring, or stakeholder communication.
02

Core Expertise

Your specific instructions, heuristics, and approaches. Not vague platitudes — the actual rules-of-thumb you’ve developed over years of practice.

## Instructions
- Apply reversibility framework: bias toward speed for
  reversible choices, analysis for irreversible ones
- Prioritize features using ICE scoring weighted by
  regulatory risk
03

Decision-Making Framework

How you evaluate tradeoffs and make choices. This is the hardest thing to transfer to AI and the most valuable once captured.

## Decision-Making
- Two-way door: ship this week, measure, iterate
- One-way door: require sign-off from compliance + eng
- Default to async; reserve sync time for debates
04

Working Style

Your communication preferences, voice, and boundaries. This is what makes AI output sound like you instead of a generic chatbot.

## Communication Style
- Executive summary first, details below the fold
- Use data to support, never to intimidate
- “Here’s what changed” over “per my last email”
HOW TO INSTALL YOUR SKILL

Claude Code

Add your SKILL.md content to your project’s CLAUDE.md file. Claude Code reads it automatically at the start of every session.

Claude.ai

Go to Settings → Custom Instructions. Paste your SKILL.md content. It applies to all new conversations.

Cursor

Save as .cursorrules in your project root. Cursor loads it as context for every AI interaction in that project.

Other Tools

Works with Windsurf, GitHub Copilot, and 40+ other tools supporting custom system prompts. Any tool with a “custom instructions” or “system prompt” field can use your SKILL.md.

MAINTAINING YOUR SKILL

It should evolve

Your expertise isn’t static. Come back quarterly and run a new interview to capture what you’ve learned.

Multiple skills, multiple domains

You’re not one thing. Create a skill for your PM work, another for your side project, another for your mentoring style.

Edit freely

It’s a plain text file you own. Open it in any editor, tweak the wording, add examples, remove things that don’t land right.

CREATE YOUR SKILL

Ready to create your skill?

5 minutes. No sign-up. Just a conversation about what you know.

Start a Quick Chat