Playing to Win

Roger Martin and A.G. Lafley's 5-question integrated cascade for strategy — distilled from the 2013 book Playing to Win: How Strategy Really Works (Harvard Business Review Press) plus 12+ years of Martin's post-book refinements in HBR, his Medium "Playing to Win / Practitioner Insights" series, and podcast interviews (including Lenny Rachitsky, 2024).

This skill helps you think in the cascade, not just recite it. It's opinionated because Martin is opinionated: strategy is an integrated set of choices, not a checklist. Applying one question without the others isn't Playing to Win — it's the thing Martin spends most of his airtime critiquing.

When this skill activates

Use this skill when the user is:

• Drafting or critiquing a strategy document (theirs or someone else's).
• Deciding whether/how to enter a market, launch a product, or move into a new segment.
• Working out what "winning" means for their company, product, or team.
• Struggling to articulate their competitive edge or unfair advantage.
• Confused about the difference between strategy and planning (a distinction Martin cares about deeply).
• Doing annual planning or strategy reviews.
• Reviewing an offsite output that "looks like strategy" but might not be.

Do NOT use this skill when:

• The user is pre-product/market fit as a startup founder — Martin himself says the cascade is not the right tool for pre-PMF search (his words in Lenny's podcast, 2024). Suggest a lean/discovery frame instead.
• The user is asking a purely operational or execution question ("how do we ship faster?"). Martin explicitly separates strategy from ops.
• The user's question is really about culture, hiring, or organizational design without a competitive-choice angle.
• The user just wants a summary of Playing to Win. Give the book link and don't run the cascade.

If the user's situation is ambiguous, ask one clarifying question before applying the cascade.

The cascade at a glance

Five questions, always answered together, always reinforcing each other:

1. What is our winning aspiration? — what does winning look like for us, for whom, and why does it matter?
2. Where will we play? — which markets, segments, channels, geographies, product categories, value-chain stages?
3. How will we win there? — differentiation or low cost, grounded in a real customer need and a real competitive advantage.
4. What capabilities must we have? — the reinforcing set of things we have to be uniquely good at to win this way, in this place.
5. What management systems do we need? — the structures, measures, and processes that build and maintain those capabilities over time.

Martin's canonical formulation: "Strategy is an integrated set of choices that compels desired customer action."

How to use this skill in a session

1. Understand what the user is actually doing. Are they drafting from scratch, critiquing, arguing with a co-founder, pressure-testing a decision? The move differs. Read references/prompts.md for shape.
2. Walk the cascade one question at a time, with integration. After each answer, connect it forward and back — a winning aspiration that doesn't survive the where-to-play question is not a strategy. Load references/method.md for the canonical definition of each question and how Martin describes their integration.
3. When the user's answer sounds like planning, goals, ambitions, or "we want to be #1" — challenge it. These are Martin's most-named anti-patterns. Load references/heuristics.md and use the specific anti-patterns with attribution. Don't blur — Martin is explicit about what bad strategy looks like.
4. When the topic goes beyond the book — pull post-book material. Martin has said much more about capabilities and management systems since 2013 than the book contains. He has also refined his views on "competitive advantage is fleeting", scale sensitivity, and modern differentiation. Load references/post-book.md.
5. Match Martin's voice when responding on his framework's behalf. He's direct, uses specific cases (P&G/Olay, Vanguard, Southwest, Four Seasons, Westlaw) to stand in for whole classes, and pushes back on jargon ("execution", "strategic planning", "resource-based view"). Load references/voice-and-tone.md.
6. Cite sources. When you introduce a specific device or quote, name the source: book chapter, HBR article, Lenny episode, Medium essay. Attribution respects Martin's work and lets the user go deeper.

Deep references (load as needed)

• references/method.md — the 5 questions in depth, in Martin's own terms, with integration notes.
• references/heuristics.md — do's, don'ts, gotchas, pro tips, anti-patterns, common misapplications. Quoted with attribution.
• references/post-book.md — Martin's material published or said AFTER the book: Practitioner Insights (Medium), HBR articles, podcasts. This is the differential of this skill.
• references/author-live-sources.md — index of every place Martin publishes regularly (Medium ~260+ essays, YouTube playlist, rogerlmartin.com archive, podcast appearances). When the user has a specific situation (offsite, chief strategy officer decision, HTW stuck, pivot question), consult this index and either point them to the specific piece or WebFetch it for depth.
• references/voice-and-tone.md — how Martin actually talks about strategy. Voice is part of the method — his intolerance for "playing to play", his P&G / Southwest / Four Seasons trio, his blunt "you'll never amount to anything" line about people who defer strategy.
• references/applications.md — when the cascade fits, when it doesn't, adjacent frameworks (Rumelt's kernel, Porter's Five Forces, Wardley Mapping) and when each is the better tool.
• references/examples.md — worked cases Martin has used publicly (P&G/Olay, Vanguard, Southwest, Four Seasons, Westlaw, Tesla, Lego).
• references/prompts.md — invocation templates for common tasks.
• references/sources.md — everything consulted, with links.

Non-negotiables

• Fidelity to Martin. This is his cascade, not a generic strategy skill. Don't blend with Rumelt's kernel or Porter's Five Forces unless the user explicitly asks. If the user's situation would be better served by a different framework, say so and point them at it — see references/applications.md.
• Integration is the point. The 5 questions must reinforce each other. A user who wants to answer only "where to play" and skip the rest is not doing Martin's method. Push back gently but clearly.
• Attribution matters. When quoting Martin, cite. When paraphrasing, name the source. This skill is a distillation, not a substitute for Martin's writing.
• Explicit uncertainty. When Martin has publicly refined or reversed a position (e.g., his post-book views on "competitive advantage is fleeting"), name the shift. Don't collapse 12 years of thinking into a single flat voice.

Attribution and acknowledgement

Roger Martin — Canadian strategy thinker, former dean of the Rotman School of Management (University of Toronto), Thinkers50 #1 (2017), co-author with A.G. Lafley of Playing to Win: How Strategy Really Works (Harvard Business Review Press, 2013). Also author of The Opposable Mind (2007), The Design of Business (2009), Creating Great Choices (2017), When More Is Not Better (2020), A New Way to Think (2022).

• Book: Playing to Win on Amazon · HBR Store
• Martin's Medium ("Playing to Win / Practitioner Insights" series): https://rogermartin.medium.com/
• Martin on Lenny's podcast: episode (2024) — one of the richest single sources for post-book material.

This skill is not endorsed by Roger Martin. It's Marcos Sponton's structured reading of Martin's public work. If Martin himself wants to correct or endorse anything here, PRs welcome.

• Skill maintained by: Marcos Sponton. Feedback, corrections, and PRs are welcome. See the repo's README for how to contribute.