How to Create Winning Strategies

Roger Martin, Designing Strategy

Roger Martin is a bit of a legend in the strategy world. His book Playing to Win, written with former Procter & Gamble CEO A.G. Lafley, is a favorite in business schools. And decades of work consulting with some of the world’s most recognizable companies have cemented his place as one of today’s leading business thinkers. In this conversation, get an inside look at Roger’s approach to business strategy and hear about our newest course, Designing Strategy. 

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Ten years ago, Canada’s accomplishments in the tennis world could be summed up in two words: virtually nonexistent. But with a few strategic choices, a lot can change in a decade.

Roger Martin, a strategy advisor who had a hand in the outcome of Canada’s tennis aspirations, says strategy really comes down to making choices. And while many people think of it as a complicated, onerous task that doesn’t have much of an impact, it doesn’t have to be that way. “My lifelong goal is to make strategy three things—simple, fun, and effective,” he says.

Roger’s approach to strategy has led to his recognition as one of today’s leading management thinkers. He’s helped countless companies, nonprofits, and organizations of all types achieve lasting business success. Now, his approach is at the center of our course, Designing Strategy, created in collaboration with Roger and his longtime colleague Jennifer Riel, also an advisor, professor, author, and IDEO’s global director of strategy.

We sat down with Roger for our Creative Confidence Podcast to get his take on today’s most pressing strategy challenges, advice for overcoming them, and why combining creativity and rigor is critical to creating winning strategies. Plus, read on to learn what happened when Canada’s tennis organization asked what would have to be true to become an international force.


“The future is uncontrollable, but you can shape your participation in it.”
Roger Martin


Challenges blocking effective strategy

While many people might feel that the fast pace of change in today’s economy and business landscape is the leading factor in hindering their strategy work, Roger offers a gentle reminder—it’s always been that way, and it’s not likely to slow down. It’s a challenge to keep up with new technology and innovations, but don’t use that as an excuse to wait in the wings. Use strategy to empower yourself.

Roger maintains the mindset that “the future is uncontrollable, but you can shape your participation in it.”

As business strategy has evolved into a discipline, new challenges have emerged. While not an exhaustive list, Roger observed five common challenges that strategists and teams encounter.


Strategy is treated as a thought exercise with no grounding in the real world and no real impact on the organization.


Strategy is set by a few C-level executives, and the rest of the organization is supposed to simply execute on what they’re told.

Purely analytical

Strategy can be framed as if it’s all about mitigating risks with budgets and financial forecasts, with no emphasis on building innovative ideas for the future.


Strategy ends up as a broad mission statement that teams and employees don’t feel connected to, much less know how to apply in their everyday work.


Strategy is done once a year, then sits on a shelf with no real action plans against it.

We polled the IDEO U community and found that while all of these challenges resonate, most people struggle with strategy that feels unactionable or top-down.

The Biggest Strategy Challenges

Roger’s advice for unactionable, top-down strategy

For strategy that feels unactionable, Roger says to bring it back to real people. And who is the best proxy for a real person? Yourself.

When crafting strategy, “don’t do it for a theoretical person,” Roger says. Ask yourself, “Would I know what to do with this direction?” If the answer is no, there’s a pretty good chance no one else will either. Keep the employees, leaders, and stakeholders in mind who will need to execute this strategy.

If strategy at your organization feels mandated by senior leaders, Roger says the best place to start is to control what you can control. Even if you feel disconnected from the strategy that was set, know that “in your own domain, you have choices to make.” If you do a good job executing the strategic vision at your level, within your team, leadership will see and take note.

In fact, strategy is not something relegated to people in the C-suite. And Roger doesn’t consider it optional. “It’s not everybody can, it’s everybody must,” he says of making strategic choices.

“Everybody in an organization is a strategist, even down to the individual,” he says. “The organizations that embody that do the best.“

Take the Four Seasons hotel. Everyone in the company is empowered to make choices to execute on the greater strategy, including frontline staff. If a customer needs a ride to make a meeting, the bellhop can decide to grab the hotel’s car and drive them, even though that’s not typically in their job responsibilities. Everyone knows that what’s important is not hierarchy, but rather an individual’s ability to be creative and take action in service of the big picture.

Strategy needs creativity and rigor

Today’s business strategy has shifted away from its original intent. What began as a creative act has adopted the approach of analysis, a craft established by Aristotle more than 2,500 years ago. Analysis has many benefits, but you need creativity too. Roger says, “Your rigorous job is to imagine possibilities and choose the one for which the strongest and most compelling argument can be made.”

If companies are set on using only analysis to understand business opportunities, they will fail because you can’t analyze an idea that has never existed. “It will make sure they don't invent the future, somebody else will,” he says. “And that somebody else will put them out of business.”

The most important question in strategy

To tap into a creative mindset, Roger asks a seemingly simple question—“What would have to be true?”

The origin of this question comes from a meeting he had with a mining company many years ago. As they tried to decide on their next move, each person in the room had a different opinion about existing limitations and opportunities, or what is true right now. The meeting descended into adversarial position-taking until Roger posed a question that sparked a more creative way of thinking. He asked them to specify what would have to be true for the option on the table to be a fantastic choice.

This question helps you create an argument for each strategic possibility you’re considering, design tests to learn more about each possibility, and make an educated decision based on data instead of conjecture. If everything that would need to be true can likely be true, then that possibility is a winning strategy.


“Everybody in an organization is a strategist, even down to the individual.”
Roger Martin


How Canada made strategic choices to become a tennis powerhouse

Roger’s approach to strategy applies beyond the typical boardroom—every kind of organization, from nonprofits to sports teams, can use this strategic approach to find success. Take Tennis Canada, where Roger joined the board of directors in 2005. At that time, players were representing Canada in several events, but the country had never accomplished anything to speak of in the world of tennis and never produced any champions.

First, the organization identified the problem—they were resource strapped and stretched too thin across too many events. To see greater success, they had to make a choice between continuing to do a little bit of everything and representing Canada internationally, or focusing on some things and not others and operating differently.

To help make that decision, they explored the conditions that would have to be true to make the strategy of refining their focus a winning one. Some of those conditions were that they’d have to be able, despite scarce resources, to hire world-class coaches to mentor young players and secure more sponsors. They tested those conditions and found that the coaches and sponsors they’d want to work with would say yes if the opportunity was presented.

“There's a certain level of confidence that you've got to get to, to enable you to take bold action,” Roger says. Even though the decision was still a risky one, the team became more confident that their conditions would most likely be true if they were to shift their operating strategy. They were ready to make a choice.

“You can never predict the future entirely,” Roger says. “But you can shorten your odds.”

In 2019, Tennis Canada is seeing the results of that strategy. Bianca Andreescu, the 19-year-old Canadian prodigy, recently triumphed at the U.S. Open by defeating one of the most dominant players in tennis history, Serena Williams. Overall, Canada has seen six Grand Slam Junior champions since shifting their strategy. Tennis great and commentator John McEnroe said, “Who would have ever thought Canada would become a tennis superpower?” The answer is nobody.

The beauty of this success is in part how it perfectly illustrates the impact of making choices. Roger wrote about Tennis Canada’s transformation, commenting that the key to a winning strategy starts with great ambition and vision. You can’t win by copying others, and you can’t wait to be handed an opportunity.

“Strategy is for shaping the world rather than accepting the consequences.”

Learn this distinct and actionable process for making strategic choices for your business, team, or organization in our 5-week online course, Designing Strategy.

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