Playing to Win

This skill should be used when the user asks to evaluate, sharpen, red-team, or pressure-test a business idea, offer, market choice, product, or strategic move using Roger Martin and A.G. Lafley's Playing to Win choice cascade. Triggers on phrases including "Playing to Win", "P2W", "where to play", "how to win", "winning aspiration", "build me a strategy", "red-team this idea", "pressure-test this", "Plan to Win", or "build a strategy framework around this project". Produces a structured 12-section output across four phases (Diagnosis, Cascade, Stress Test, Verdict), writes a persistent markdo

7 starsTesting & QA

Install

skills CLI (Claude Code, Cursor, Codex and more)

npx skills add paultaki/playing-to-win --skill playing-to-win

Manual install

git clone --depth 1 https://github.com/paultaki/playing-to-win.git /tmp/playing-to-win
mkdir -p ~/.claude/skills
cp -r /tmp/playing-to-win/. ~/.claude/skills/playing-to-win

Personal skills live in ~/.claude/skills. Use .claude/skills in a project folder to share a skill with your team.

From the SKILL.md

# Playing to Win Strategy Builder

## Purpose

Apply Roger Martin and A.G. Lafley's Playing to Win choice cascade directly to a business idea, offer, market move, or running product. Assume the user already knows the framework. Apply it. Do not teach it.

**Core rule:** Strategy = choices. Reject vague goals, broad markets, "AI as differentiation," or "we serve everyone." Narrowing is the point.

**Default voice:** Direct, skeptical, practical. Summary first, plain operator language, no fluff, no fake encouragement.

## When to Use

Trigger this skill when the user asks for any of:

- "Build me a Playing to Win framework around [idea/project/offer]"
- "Pressure-test this idea" / "red-team this strategy"
- "Where should we play?" / "How do we win?"
- "Should I proceed with [X]?"
- "Sharpen this positioning"
- Strategy evaluation inside an open project codebase

**Do not trigger** for general business advice, framework explanation, motivational coaching, or generic startup tips.

## Workflow

### Step 1 — Frame the Subject

Identify what is being evaluated:

- **Raw idea** — concept-only, no code, no validation
- **Existing offer** — already selling, evaluating sharpening
- **Project codebase** — running product, evaluating strategy fit
- **Market move** — repositioning, expansion, new wedge

If a project codebase is open, run Step 2a and 2b. Otherwise skip to Step 3.

### Step 2a — Project Codebase Discovery

Read the full skill on GitHub

Details

Skill name: playing-to-win
Repository: paultaki/playing-to-win
Repo updated: 9 June 2026

FAQ

What does the Playing to Win skill do?

How do I install the Playing to Win skill?

skills CLI (Claude Code, Cursor, Codex and more): npx skills add paultaki/playing-to-win --skill playing-to-win. Skills go in ~/.claude/skills (personal) or .claude/skills (project), and Claude loads them automatically when a task matches the description.

Is Playing to Win popular?

It lives in paultaki/playing-to-win, which has 7 GitHub stars and 0 forks.

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