5 Essential Questions to Craft a Winning Strategy with Roger Martin
- Aisha Washington
- 18 hours ago
- 7 min read
Strategy is often presented as the domain of senior executives, consultants, and business-school specialists. Roger Martin, author of Playing to Win, takes a more practical view: people throughout an organization make choices that influence customers, allocate resources, and determine whether a product succeeds.
In his conversation on Lenny’s Podcast, Martin explains why strategic thinking feels difficult and offers a framework for making it manageable. His “choice cascade” organizes strategy around five connected questions—from defining a winning aspiration to building the management systems needed to deliver it.
Why Strategy Cannot Remain in the Executive Suite
Organizations commonly tell senior leaders to think strategically while asking everyone else to concentrate on execution. Martin argues that this division is misleading. Employees closer to products and customers routinely make decisions with strategic consequences, even when those decisions are not labeled as strategy.
A brand manager may select a customer segment, adjust a product proposition, or decide where to spend a marketing budget. A product manager may prioritize one user problem over another. Each choice changes how the company competes.
Martin points to Procter & Gamble as an organization that has historically treated decisions made below the executive level as strategically important. A brand can gain or lose relevance because of choices made several layers down the hierarchy. Giving those employees a strategic framework can therefore improve both ownership and outcomes.
This does not mean every employee should independently reinvent the company’s direction. It means people need to understand the larger set of choices and see how their decisions support—or undermine—it.
Why Developing a Strategy Feels So Difficult
Strategy poses both an intellectual and an emotional challenge.
The intellectual difficulty comes from interdependence. A company cannot choose a market without considering how it will succeed there. It cannot promise a distinctive customer experience without building the capabilities to deliver it. Each answer must be compatible with the others.
The emotional difficulty comes from commitment. A genuine strategy closes off alternatives. Choosing one customer group, distribution model, or competitive advantage means declining other plausible opportunities. Leaders may resist that constraint because keeping every option open feels safer.
Yet refusing to choose is itself a choice. It usually produces scattered investment, conflicting priorities, and an organization that cannot explain why customers should prefer it.
Martin is also critical of strategy education that remains too abstract. In his view, theories centered primarily on accumulating valuable resources do not adequately explain which resources a company should build or why they will matter in a particular market. He similarly observes that many consulting firms now devote substantial attention to implementation programs, digital transformation, and post-merger work, leaving fewer opportunities to learn the craft of forming strategy itself.
Strategy as a System of Choices
Martin defines strategy not as a plan, forecast, mission statement, or list of initiatives, but as an integrated set of choices intended to produce a desired response from customers.
A company controls decisions such as what it builds, whom it hires, where it distributes, how it advertises, and which capabilities it funds. It does not control the customer. Strategy connects the former to the latter: the company makes choices in the hope that customers will buy, subscribe, recommend, or remain loyal.
The framework for making those choices consists of five questions:
What is our winning aspiration?
Where will we play?
How will we win there?
Which capabilities must we possess?
Which management systems will build and sustain those capabilities?
These questions form a cascade because each answer shapes the next—and later answers may reveal that earlier ones need revision. The result should be a coherent theory of success rather than five disconnected statements.
Question 1: What Is the Winning Aspiration?
A winning aspiration describes the meaningful outcome the organization wants to create. It provides direction, but it should do more than express an ambition to grow, lead, or capture market share.
Martin recommends connecting the aspiration to customers. A strategically useful ambition explains whose life or work will improve and how. That framing forces a company to consider the customer action on which commercial success ultimately depends.
This distinction separates “playing to win” from merely participating. A business may call itself innovative or customer-focused, but those claims have little strategic value if buyers see its offering as interchangeable with alternatives. If customers switch as soon as a competitor cuts its price, the company may be present in the market without possessing a compelling reason to win.
Customer behavior, not internal rhetoric, is the sharper test.
Question 2: Where Will We Play?
“Where to play” defines the competitive field. The decision can include customer segments, geographic markets, product categories, distribution channels, and a company’s position within the value chain.
Specificity matters. “Serving product teams,” for example, may still leave unanswered whether the primary users are product managers, designers, engineers, or executives. It also matters whether the product will be sold directly, distributed through a platform, or embedded inside another offering.
Martin uses examples such as Four Seasons to show that value-chain position is a strategic decision. The company concentrated on managing luxury hotels rather than treating property development and construction as inseparable parts of the business. That boundary helped it specialize in the service experience.
Distribution choices can be equally consequential. A developer that depends on Apple’s App Store gains access to customers but also accepts the platform’s rules and economics. A provider such as Thomson Reuters can strengthen its position by integrating information directly into professional workflows, reducing the effort required for customers to adopt and use it.
A large market alone is not a sufficient reason to enter. In the discussion of FigJam, Martin argues that a stronger rationale would begin with an underserved customer problem. Market size may indicate opportunity, but unmet demand offers a more credible foundation for deciding where to compete.
Question 3: How Will We Win?
“How to win” is a theory about why customers will choose one company over the available alternatives in its selected market.
Two familiar routes are cost leadership and differentiation. Vanguard built a powerful position around low-cost asset management, while Southwest Airlines used an efficient operating model to offer lower fares. LEGO and Procter & Gamble illustrate differentiation through brands and products for which customers perceive distinctive value.
Cost leadership typically requires substantial scale. Differentiation may be possible at a smaller size, although Martin notes that many markets have become increasingly sensitive to scale.
The choice is not merely a slogan. Claiming to offer the easiest experience, best service, or most innovative product creates an obligation to prove that difference in customer behavior. If a company can achieve neither a meaningful cost advantage nor a valued distinction, it may need to reconsider its playing field.
Martin also cautions against treating the low-cost-versus-differentiation distinction as an exhaustive law. Strategic possibilities can be more varied. The essential requirement is a credible explanation of why the chosen customers will respond favorably.
Question 4: What Capabilities Are Required?
A strategic promise becomes real only when supported by capabilities. These are the activities a company must perform unusually well to make its proposed advantage believable and repeatable.
A business seeking to be the easiest provider to work with might need superior onboarding, responsive support, thoughtful product design, and close integration with customer workflows. A learning curve can also matter: early experience may help a company improve faster than later entrants.
Martin’s discussion of Four Seasons illustrates how capabilities reinforce one another. The company’s interpretation of luxury emphasized attentive service that replaces the comforts and support guests leave behind. Delivering that experience required experienced employees who could recognize individual needs.
Because hotel work often experiences high employee turnover, Four Seasons could not rely on service training alone. It needed a different approach to recruiting, onboarding, retention, and career development. Martin cites turnover of roughly 10 percent as evidence of a workforce system that helped preserve the experience necessary for personalized service.
The strongest advantages often emerge from a complex combination of capabilities. A single feature or cost reduction may be easy to copy; an interconnected operating model is harder to reproduce.
Question 5: Which Management Systems Will Sustain the Advantage?
Management systems turn required capabilities into ongoing organizational behavior. They include measures, incentives, decision processes, hiring practices, development programs, and routines for reviewing performance.
This fifth question prevents strategy from ending as a presentation. If the chosen way to win depends on outstanding service, the company must recruit and reward accordingly. If success requires rapid learning, leaders need systems that capture customer feedback, test assumptions, and spread knowledge.
Capabilities and management systems together form a company’s characteristic way of operating. Their value lies not only in producing good performance today but also in making the advantage durable.
Martin describes competitive advantage as fragile rather than necessarily brief. A strong position can last, but only while the underlying choices remain relevant and the organization continues supporting them. Companies often overestimate their “moats,” particularly when an early lead rests on a feature that competitors can quickly reproduce.
Some advantages persist because established competitors hesitate to copy them. Amazon benefited when traditional retailers were slow to commit to e-commerce, while Tesla advanced as incumbent automakers struggled to reconcile electric vehicles with their existing economics. Such reluctance can create room, but no barrier should be assumed permanent.
Strategy Must Move When Customers Move
Even a successful choice cascade needs revision when customer behavior changes. Market leadership in one era does not guarantee relevance in the next.
Martin points to traditional carmakers confronting electric vehicles and Microsoft’s difficulty translating PC operating-system dominance into mobile leadership. Existing assets can become psychological constraints when companies confuse the business they currently operate with the value customers actually seek.
Vanguard’s eventual embrace of exchange-traded funds offers another lesson. Its founder initially opposed ETFs, but customer preferences continued moving in that direction. Resisting a durable shift in demand rarely preserves a company’s position.
Adaptation does not mean chasing every trend. It means revisiting assumptions when evidence shows that customers, channels, technologies, or competitors have changed the playing field.
A Practical Way to Practice Strategy
Martin presents strategy as a problem-solving discipline. It begins with a gap between the outcome an organization wants and the outcome its current choices produce.
Rather than attempting to perfect the entire system at once, teams can identify the most painful gap. The constraint might be an unclear customer need, weak distribution, an unavailable capability, or a management process that rewards the wrong behavior. Addressing that constraint creates a better set of choices and reveals the next problem worth solving.
This iterative approach also makes strategic thinking less intimidating. The five questions provide structure, while repeated application develops judgment.
Martin’s closing message is encouraging: great strategists are made through practice, not born with a special instinct. Anyone can begin by noticing where results could be better, examining the choices behind that gap, and deliberately testing a more coherent alternative. Operational pressure is not a reason to postpone strategy; it is often the clearest source of the problems strategy needs to solve.
