SKILL.md
Playing to Win Framework
Overview
A strategic framework to create focus by making an integrated set of choices about where the product will compete and how it will succeed, rather than trying to be everything to everyone.
Core principle: Strategy is an integrated set of choices, not a list of goals.
The Four Steps
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│ 1. DEFINE WINNING ASPIRATION │
│ What does "winning" look like for us? │
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│ 2. CHOOSE WHERE TO PLAY │
│ Markets / Segments / Personas │
│ Be SPECIFIC (not "everyone") │
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│ 3. DETERMINE HOW TO WIN │
│ Value proposition / Differentiation │
│ What makes us win in that market? │
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│ 4. EXECUTE │
│ Build capabilities and systems │
│ Align team around choices │
└─────────────────────────────────────────────────────────────────┘Key Principles
| Principle | Description |
|---|---|
| Explicit choices | Where to Play AND How to Win |
| Integration | Choices must reinforce each other |
| Focus | Saying "no" is as important as saying "yes" |
| Specific targets | Name the segments, not "broad market" |
Common Mistakes
- Skipping "Where to Play" and building for everyone
- Building features for every user type
- Strategy = goal list rather than integrated choices
Source: Annie Pearl (Calendly CPO) via Lenny's Podcast