I recently picked up Playing to Win: How Strategy Really Works by A.G. Lafley and Roger L. Martin. I’ve been thinking about how to apply its ideas to my responsibilities as a director of product design, particularly as I plan for the year ahead. One of the first ideas that challenged my thinking was surprisingly simple: strategy is about making choices. That sounds obvious until I consider how often organisations approach strategy through the work they intend to deliver. We build roadmaps, identify priorities, establish objectives, and allocate resources. We discuss which products need attention, which customer experiences need improvement, and which capabilities our teams are missing.
All of these activities matter. But they don’t necessarily explain why we’re making those investments, which customers we’re choosing to serve, or how the business expects to succeed. I’ve seen how easy it is for planning discussions to become conversations about capacity and delivery. The work becomes the focus before we’ve fully established the strategic reasoning behind it. Reading the opening chapter of Playing to Win helped me articulate a distinction I want to carry into my own leadership practice.
A roadmap describes what we intend to deliver. Strategy explains the choices that make that work worth doing.
What does it mean to make strategic choices?
Lafley and Martin introduce strategy as a connected set of decisions that help an organisation create value and compete successfully. Their argument is that an organisation cannot pursue every opportunity, serve every customer equally, or invest in every capability at once. Resources are limited, customer needs differ, and competitors are making choices of their own. Strategy requires deciding where the organisation will focus its attention and how it intends to succeed in those areas.
The authors organise this thinking around five questions, which they call the Strategic Choice Cascade.
- What is our winning aspiration? What are we trying to achieve?
- Where will we play? Which customers, markets, needs, and opportunities will we prioritise?
- How will we win? Why would customers choose our offering over the alternatives?
- What capabilities do we need? What must the organisation be particularly good at to deliver that value?
- What management systems will support those choices? How will we make decisions, measure progress, and adapt?
What interests me is how these questions depend on one another.
An organisation might have an ambitious objective but lack the capabilities to achieve it. It might invest in excellent technology without understanding which customer problem that technology should solve. It might have talented teams delivering strong individual products without a clear reason for customers to choose the overall experience.
The framework encourages leaders to examine those relationships instead of treating strategy, execution, and organisational design as separate conversations. It also makes one thing clear: making a choice means accepting that other opportunities will receive less attention. That is often the difficult part.
What a skincare brand taught me about strategy
One of the examples Lafley and Martin use is the reinvention of Olay, a skincare brand owned by Procter & Gamble. I found this example particularly useful because it demonstrates that business success does not come from improving a product in isolation.
By the late 1990s, Oil of Olay was struggling to remain relevant. Its traditional positioning was associated with an ageing customer base, while the broader skincare market was changing. Customers were becoming more interested in products that addressed early signs of ageing, and competing brands offered different combinations of quality, credibility, and price. P&G could have responded by improving the existing product, refreshing its packaging, or increasing advertising. Instead, the company reconsidered the choices behind the brand. The team identified an opportunity among women beginning to notice signs of ageing, rather than concentrating only on the brand’s traditional older audience. It developed more advanced products, changed the brand’s presentation, and positioned Olay between conventional mass-market skincare and higher-priced prestige products.
The distribution decision was equally important. Rather than relying on prestige department-store channels, Olay continued to compete through mass retail while offering products with stronger performance claims and a higher perceived value. The authors describe this positioning as mastige, combining elements of mass-market accessibility and prestige.
What stayed with me was how the decisions supported one another. The target customer influenced the product. The product influenced the price. The price influenced perceptions of quality. The distribution model shaped how customers encountered and purchased the brand. Changing one element without considering the others could have weakened the overall proposition.
I don’t see the Olay example as a formula to copy. I see it as a reminder that successful strategy depends on the relationship between decisions. For design leaders, that raises an important question. Are we improving individual experiences, or are we helping the organisation build an experience that supports a deliberate business choice?
The difference between improving a channel and choosing where to compete
This question becomes particularly relevant in financial services. In my work at Money Mart, I think about customer experiences that extend across websites, mobile applications, transactional communications, contact centres, and branches. Each channel has its own requirements, stakeholders, technologies, and operational constraints. From a delivery perspective, it is tempting to organise priorities around those channels.
The website needs improvement. The application process needs attention. The mobile experience requires new capabilities. Transactional communications need clearer language.
These can all be legitimate priorities. But improving them independently does not necessarily create a coherent customer experience. Consider a hypothetical customer applying for a financial product. They begin on the website, complete part of an application, and receive an email requesting additional information. Later, they open the mobile app to check their progress. Uncertain about the next step, they contact customer support. The support representative may not have the context needed to help immediately, leaving the customer to repeat information they have already provided.
Every individual channel might be performing according to its own operational measures, yet the customer still experiences unnecessary effort and uncertainty. This example is illustrative, not a description of a measured Money Mart journey. But it reflects a challenge common to organisations operating across digital and assisted channels. The strategic question is not simply how to improve each touchpoint. It is which customers and needs the business intends to prioritise, and what kind of experience will make its offering valuable to them. This is where the book’s distinction between where to play and how to win becomes useful.
Where to play is about choosing the customers, markets, needs, and opportunities the organisation will pursue.
How to win is about determining what will make the organisation’s offering more valuable or attractive than the alternatives in those chosen areas.
These decisions belong together. For example, imagine two financial-services providers. One chooses to focus on customers who are comfortable completing financial transactions independently. Its strategy might prioritise fast digital completion, straightforward self-service, and low operational complexity. Another chooses to focus on customers who value digital convenience but also want access to human guidance when making financial decisions. Its strategy might prioritise continuity between digital and assisted services, understandable information, and support that preserves the context of the customer’s interaction.
Neither approach is automatically better. Each represents a different set of choices about customers, value, investment, and operational capability. A design solution that supports one strategy might be inappropriate for the other. That is the distinction I want to bring into product planning conversations. Before asking which interface should be redesigned, I want to understand which customer need we’re prioritising and why the proposed experience matters to the business.
I encountered a similar relationship between customer behaviour and business priorities while leading ecommerce work at Roots Canada. By examining how customers moved through browsing and checkout, we could focus on changes that addressed meaningful friction rather than treating each page as an independent design problem. I explore those decisions in my case study, Improving ecommerce conversion through better customer journeys.
Winning should create value for customers and the business
The language of winning can sound heavily commercial, especially in financial services. I think it deserves careful interpretation. For a business, winning may involve sustainable growth, stronger customer relationships, improved efficiency, or a competitive advantage. For customers, the value may be different. They want to understand their options, make informed decisions, complete necessary tasks, and receive appropriate support when something becomes difficult.
These outcomes should reinforce one another. A faster application might increase completion, but speed alone is not a sufficient measure of success if customers misunderstand the financial commitment they are making. Reducing contact-centre calls might improve operational efficiency, but fewer calls do not necessarily indicate that customers are getting the help they need. Similarly, increasing chatbot containment might look positive in a dashboard while leaving some customers with unresolved questions.
As a design leader, I want us to examine the relationship between commercial measures and customer outcomes. That means considering completion, comprehension, accessibility, service resolution, complaints, and customer effort alongside business performance. It also means recognising the limits of design’s authority.
Product design can bring customer evidence, identify friction, propose alternatives, and help teams evaluate trade-offs. Decisions about lending policy, risk, compliance, and commercial priorities require shared accountability across the organisation. I don’t believe design creates business value by taking ownership of every decision. It creates value by helping the organisation make better-informed decisions about the experience it offers.
The role of design leadership is not to make every experience better independently. It is to help the organisation decide which experiences matter, why they matter, and how they work together.
The strategy should influence how we organise the team
Another idea from the book connects directly to the work I’m doing as a design leader. Once an organisation decides where it intends to compete and how it expects to succeed, it needs the capabilities to support those choices. This sounds straightforward, but it has significant implications for organisational design.
I’ve been thinking about how to structure a product design team around customer journeys, shared experience foundations, and the capabilities required to support a growing digital business.
One possible approach would be to assign a designer to each channel. A website designer. A mobile designer. A designer responsible for transactional communications. That structure creates clear platform ownership, but it can also reinforce the same organisational boundaries customers are forced to cross. If the strategic ambition is to create a more connected customer experience, the team needs a way to work across those boundaries.
That might mean assigning designers to customer problems such as acquisition, lending, servicing, and assisted experiences, while supporting them with shared capabilities in design systems, content, research, and engineering. It changes the conversation from who owns a screen to who is accountable for understanding and improving a customer problem.
This is a direction I’m exploring in my operating-model planning, rather than a claim that every proposed role or capability is already established. The important lesson is not that every design organisation should adopt the same structure. It is that the structure should support the strategy, rather than allowing the existing structure to determine the strategy.
- A company prioritising rapid experimentation may need particularly strong research, analytics, and experimentation capabilities.
- A company operating across multiple products and channels may benefit from shared interaction standards, design systems, and content governance.
- A company investing in AI-assisted experiences may need stronger capabilities in evaluation, transparency, accessibility, and human oversight.
These investments should follow a clear understanding of what the business is trying to achieve. Otherwise, organisational planning can become a discussion about roles and tools without a convincing connection to customer or business value.
This thinking also informs how I’ve approached building a product design operating model in financial services. The focus has been on establishing clearer ownership, governance, and decision-making practices so that design can contribute consistently across customer journeys, rather than operating as a series of disconnected delivery requests.
Making strategic choices part of everyday decisions
One of my broader reflections is that strategy cannot remain confined to leadership presentations. The authors make the point that strategic choices exist at different levels of an organisation. Senior executives make decisions about markets and business direction, while teams make choices within that context.
For design leaders, this creates a responsibility to translate business direction into decisions people can use.
- A designer working on an application flow should understand which customer problem matters most.
- A content designer should understand what information customers need to make informed decisions.
- An engineer should understand why consistency or continuity across channels matters beyond implementation efficiency.
- A product manager should be able to explain how a proposed initiative supports the chosen customer and business outcomes.
This does not require everyone to become a business strategist. It requires leadership to provide enough context for teams to make informed decisions without escalating every trade-off. I see this as an important part of design operations. Design briefs, prioritisation discussions, reviews, and post-launch measurement should help teams connect their work to the organisation’s strategic choices.
For example, if improving continuity between digital and assisted experiences were a strategic priority, a design review would need to examine more than the usability of an individual screen. It might also examine what information is preserved between channels, what customers are told about their next step, and what support employees need to resolve the interaction.
The same principle applies to measurement. We would need to understand whether customers are repeating information, whether handoffs are successful, and whether the experience is reducing avoidable effort without compromising appropriate support. These are examples of how a strategic choice could influence everyday product decisions. They are also reminders that a strategy only becomes useful when it changes how an organisation behaves.
I faced a related challenge at Booking.com, where more than 20 teams contributed to a shared partner homepage. The work required us to understand what partners actually needed, establish priorities across competing requirements, and create a clearer experience for different types of businesses. I documented that work in my Booking.com extranet homepage case study.
The difficult part is deciding what not to pursue
As I reflect on the book, I think this may be the most demanding lesson for leaders. It’s relatively easy to identify opportunities for improvement. Most design teams can produce a long list of customer problems, inconsistent experiences, missing capabilities, and potential innovations. The harder responsibility is deciding which opportunities deserve investment now, which require further evidence, and which should wait. Every commitment has a cost.
Prioritising one customer journey means allocating less capacity elsewhere. Investing in shared design foundations may reduce the resources available for immediate feature delivery. Developing a new capability may require time before its contribution becomes visible. Those trade-offs do not disappear because the organisation has ambitious objectives. They need to be acknowledged and discussed.
This is where I see the relationship between strategy and leadership most clearly. My responsibility is not to promise that the team can solve every problem. It is to make the available choices visible, explain their implications, and help the organisation commit to a direction it can realistically support. That requires customer evidence, commercial understanding, technical input, and honest conversations about organisational capacity. It also requires the willingness to revisit a choice when new information challenges the assumptions behind it.
A strategy should guide decisions without becoming an excuse to ignore evidence.
What I’m taking forward
I’m still early in reading Playing to Win, and I intend to explore its individual concepts in greater depth as I progress through the book. For now, its opening argument has changed how I want to approach strategic planning. I want to spend less time treating a roadmap as proof of strategic clarity and more time examining the decisions that justify it.
I want to ask which customer needs we’re deliberately choosing to address, how our approach creates meaningful value, and what capabilities we need to make that approach credible. I also want to be more explicit about the opportunities we’re choosing not to pursue, because those decisions are part of strategy too.
For product design leaders, this is an opportunity to contribute beyond delivery planning. We can help connect customer understanding, business ambition, organisational capability, and product decisions into a direction teams can act upon. The strongest design strategy is not the one with the most initiatives. It is the one where the choices make sense together. That’s the idea I’ll be carrying into the next chapters of Playing to Win, and into my own conversations about the future of product design.
If you’re working through similar questions in your design organisation, I’d welcome the opportunity to exchange perspectives. You can send me a message through my contact form or reach out through the ADPList mentorship programme to discuss design leadership, strategy, and team development.