Playing To Win

Strategy & Transformation

The Four Keys to Success

Roger Martin
8 min readSep 20, 2021


Copyright: Roger L. Martin, 2021

Transformation is a hot topic these days, probably too hot. Putting transformation behind anything — finance transformation, go-to-market transformation, customer experience transformation, etc. — makes the thing sound cool and important. I have gotten so many questions about transformation that I thought I would dedicate my 51st Playing to Win/Practitioner Insights (PTW/PI) piece to Strategy & Transformation: The Four Keys to Success. (Links for the rest of the PTW/PI series can be found here.)

Un-Transformational Transformations

By my observation, most transformation efforts fail to transform. The AT&T acquisition of Time Warner to transform AT&T into a “converged media and communications company,” failed utterly and was unwound at a huge loss. The Bill Ackman/Ron Johnson attempt to transform JC Penney was an expensive flop. Marissa Mayer’s effort to transform Yahoo only transformed her from high tech darling to also-ran. And Jorma Ollila’s attempted transformation of Nokia at the inception of the smartphone era ended up sealing its fate as an irrelevant player in the business it previously dominated.

It is no surprise. Transformation is a challenging thing. It is a pretty dramatic word. It is not a gentle ‘improvement,’ ‘tweaking,’ ‘course correction,’ or ‘acceleration’ of the status quo. Transformation connotes a fundamental, discontinuous change — a revolution, a reboot, a makeover — otherwise we wouldn’t call it ‘transformation’ in the first place. In many respects, transformation is set up for disappointment.

My Transformation Experience

What then can improve the odds of overcoming the transformation challenge? I will use my personal experience from three transformations which either I led or with which I was intimately involved to illustrate what I feel are the four more generalizable keys to transformation success.

The first of the three is the most dramatic large corporate transformation that I can name. That is the transformation of the Thomson Corporation from being comprised of the world’s largest newspaper company, the world’s largest textbook publisher (tied with Pearson), Europe’s largest travel company, and a major player in North Sea oil to Thomson Reuters, the leading supplier of on-line, subscription-based must-have information, analytics, and workflow solutions to professionals. I served on the board of the company for 14 years during the heart of that transformation.

The second is an historic non-profit transformation. I served as board member of Tennis Canada for 12 years (including three years as chair) starting at the inception of its transformation from an utterly irrelevant tennis nation to what is now routinely characterized by on-air by commentators, including multiple Grand Slam champion John McEnroe, as a “tennis superpower.”

The third is a transformation of an educational institution. I served as Dean of the Rotman School of Management for 15 years during which it was transformed from from the third best business school in southern Ontario to Canada’s only consequential global business school, with a faculty ranked as high as 3rd in the world in the Financial Times global ranking — after only Harvard Business School and the Wharton School.

Clear and Compelling Strategy

A transformation can’t be a proliferation of initiatives or one big acquisition. These aren’t substitutes for strategy. Successful transformation has to be underpinned by a clear and compelling strategy.

There must be a Winning Aspiration (WA). For Thomson, it was to become the leading provider of must-have information for professionals. For Tennis Canada, it was to become a leading tennis nation. For Rotman it was to become Canada’s first globally consequential business school.

Plus, there needs to be a clear Where-to-Play/How-to-Win (WTP/HTW) combination that serves and reinforces the WA. For Thomson, it was must-have data integrated into work flows of business, legal, accounting, finance, and scientific professionals. For Tennis Canada it was men’s and women’s singles (the most competitive part of the sport) and a unique hybrid of athlete development. For Rotman, it was a new way to think, relentless utility, and global scale.

You can’t set off with hope as your strategy or keep chasing the latest trend. There has to be a consistent, compelling vision of where you want the strategy to take you. But it needs to be flexible. Thomson eventually dropped financial and scientific professionals from its WTP. And Rotman absorbed design thinking and behavioral economics into its definition of a new way to think. The flexibility needs to maintain the robustness of the initial strategy rather than undermine it.


If you want a fast transformation, my advice is don’t even start. You will fail, which is one of the reasons why transformation by way of a single big acquisition is so likely to fail.

The Thomson transformation started in earnest with the 1989 sale of the first of its core businesses, oil & gas, and wasn’t substantially complete until the sale of the fourth original business, textbooks in 2007. By that time Thomson was an all-digital, online player. There has been still more transformation since 2007, but the core transformation from newspaper/textbook publisher to on-line information provider to professionals took almost two decades.

At Tennis Canada, it took six years until first green shoots to appear with Filip Peliwo and Eugenie Bouchard winning Canada’s first Junior Grand Slam singles championships in 2012. It took eight years to see Bouchard make the Women’s Wimbledon finals and Milos Raonic the Men’s semifinals both in 2014. And it took 13 years to achieve the stated goal of winning a Grand Slam singles championship when Bianca Andreescu won the US Open. Between 2014 and 2021, Canada was the only nation with both three different male and three different female Grand Slam semifinalists.

At the Rotman School, it took 15 years to double the student cohort, quadruple faculty, build a new building, and build our global reputation. That is one quarter of my working life. It was purposely slow and steady. I wanted to achieve complete transformation but without making our constituents so nervous that they would freak out at any point on the journey.


All three transformations took withering criticism in the early days. The leadership group for a transformation needs to be tough-minded and supportive of each other throughout.

At Thomson, a critical step in the transformation was the purchase of West Publishing for $3.4 billion in 1996. The analyst community slammed Thomson for overspending and rashly betting the company. But the majority owner, Ken Thomson, backed management and ignored the criticism. Successive Vice-Chairs John Tory and Geoff Beattie were instrumental in ensuring that management pushed the transformation agenda that the majority owner sought and supported, even when it required very firm pushing!

At Tennis Canada, there was brutal criticism from former leading player and national head coach, Pierre Lamarche, who wrote an influential newsletter in which he blasted Tennis Canada strategy over and over for its new strategy that he guaranteed would fail. Long time Canadian Davis Cup coach Louis Cayer left for the UK when the new strategy was put in place. But the core group made up of the Chair, two key Board members (who became the next two chairs), and the CEO held firm to the strategy.

At Rotman, one of most influential professors argued passionately and at length in the first Faculty Council discussion of the new strategy that it was going to be a disaster, a complete failure. Another leading professor resigned to go to a more prominent business school and wrote me a long letter explaining why I would be a certain failure and was a dreadful hire for the Dean’s job. Fortunately, I was supported by the University President who had my back, plus a loyal Vice-Dean Academic, and a supportive business community. Happily, the former professor came to my office seven years later to apologize and thank me for not listening to him. The latter professor wrote me letter offering to come back from the School that was no longer more prominent than Rotman. But by that point the faculty had improved so much that his academic area felt it could do better by using the faculty slot on someone better.


Growth greases the skids of transformation. If your dominant mode is the reallocation of existing resources, you will create immediate enemies of every group from whom you take resources. If instead you grow the top line, you can put all the new resources behind the transformation and slowly scale back the things that don’t fit.

Thomson revenues were $5.1 billion in 1989 and had more than doubled to $12.7 billion at the time I left the board in 2013. Tennis Canada had $3 million/year to spend on high performance as of 2005 and within five years had grown its top line enough to be able to afford to spend $12 million/year. The Rotman budget in my 15th year as Dean was just shy of ten times the size of the budget that I inherited in my first year. In all three cases, the robust growth enabled the dedication of new resources to the key transformation initiatives.

Practitioner Insights

If you are contemplating a transformation, whether leading one, supporting a leader of one, or advising on one, don’t call it a transformation. Transform rather than talk about transformation. Talk instead about the end state you seek. Very few people actually like what is involved in a transformation; they just like the end state. And I can assure you that calmness is better than agitation when you are transforming.

Then make sure to take a cold, hard look at whether you really have a strategy that can drive a transformation. Don’t be like AT&T management with some vague and sloppy notion like we are going to transform into a vertically integrated “converged media and communications company” with “owner economics” and that is why it is worth paying $85 billion for Time Warner. My critique is not 20–20 hindsight. I was on the record at the time arguing that the acquisition would be a disaster, would end the career of CEO Randall Stephenson, would be sold within five years, and for consideration of half of the purchase price. I wasn’t quite right. It was a disaster, ended Stephenson’s career, was sold in three years, but I was off by $500 million. It sold for $43 billion, and I had predicted $42.5, my bad. Or JC Penney: I predicted that strategy-free debacle too.

Take the time to think very carefully through your strategy. Test it with others. Ask what would have to be true (WWHTBT). Make sure you have a plan for overcoming the key barriers. Don’t be AT&T!

Then determine whether you have the requisite patience. Assume that the desired transformation will take a decade. If it happens faster — hurrah. But don’t go into it thinking that it will happen quickly, or you will disappoint yourself and all the people whose expectations you raised. I read once that Allied prisoners of war in World War II Japanese prison camps tended to have one of three mindsets — and only one was helpful to their surviveal. The ones who despaired from inception tended to expire. The ones who believed that they would be liberated relatively quickly also expired when their hopes were dashed. The ones who survived believed that they were in for a long, difficult journey and steeled themselves for it. It is a good analogy for business transformations.

Then build a coalition that will help you achieve resilience. Assume that you will be told you are an idiot in the early years — and told so by important, influential people. You will need the support of others around you to get through the attacks, which happily will stop when momentum starts to build.

Finally, have a growth plan. Only if you will have considerably more resources at the end of the transformation relative to the start is it even worth commencing. If the transformation involves shrinking first, don’t do it. Spend your precious life doing something else.



Roger Martin

Professor Roger Martin is a writer, strategy advisor and in 2017 was named the #1 management thinker in world. He is also former Dean of the Rotman School.