Playing To Win

Sticking with Strategy

How to Hold on to Give it a Chance

Roger Martin
8 min readJan 16, 2023


Source: Roger L. Martin, 2023

I was reflecting (happily) the other day on Canada’s first ever Davis Cup win in November 2022, an accomplishment would have been considered utterly inconceivable a decade and a half ago. But it was a specific goal of the strategy put in place in 2005. It does beg the question: how can you hang on for 17 years waiting for your strategy to achieve its desired goals? That is why I have written my 6th Year III Playing to Win Practitioner Insights (PTW/PI) piece on Sticking with Strategy: How to Hold on to Give it a Chance. You can find the previous 116 PTW/PI here.

Tennis Canada’s New Strategy

In 2005, Tennis Canada embarked on a new strategy. The goal of the strategy was to produce a Grand Slam singles championship and a Davis Cup or Billie Jean King Cup team championship. For non-tennis aficionados, the four Grand Slams are the game’s most venerable and prized tournaments — Wimbledon (since 1877), US Open (1881), French Open (1891) and Australian Open (1905). The Davis Cup is the most celebrated team competition contested by country teams and having been played annually since 1900. The Billie Jean King (BJK) Cup (formerly the Fed Cup) is the women’s equivalent of the Davis Cup and has been contested since 1963.

For a tennis outsider, that goal may seem like not a particularly big deal. If Grand Slam titles and Davis/BJK Cup wins are the top accomplishments in the sport, why not aspire to both? But in tennis history, Canada had only a single solitary player reach the semi-finals of a single Grand Slam. That was 21 years earlier, and no Canadian had come close to that accomplishment since. In fact, Canada had never at a male player ranked in the top 25 and none in the top 50 in more than 20 years. On the women’s side it was a bit better with two historical top 25 players, but both occurred way back in the 1980s.

To even compete for the Davis/BJK championship, a nation must get through rounds of competition to qualify for the ‘World Group,’ which numbers 18 teams for Davis Cup and, since 1995, 8 teams for BJK Cup. The last time the Canadian men even qualified for the World Group was 17 years earlier and the women had never qualified for the World Group since it was tightened to 8 nations.

Canada had no tennis tradition. Part of that is because of its terrible weather, which meant that in the entire country there were fewer than 500 year-round tennis courts, because they have to either be indoor or bubbled during the winter months. In contrast, any county in California or Florida would have more than 500 year-round courts thanks to their great weather. Plus, Tennis Canada was deeply in debt having just built a new stadium to avoid the men’s professional tour (ATP) pulling Canada’s top tier tennis tournament due to a tournament venue of unacceptable quality.

All of that notwithstanding, we launched a bold strategy that was a unique hybrid of the highly regimented French system and the ‘free market’ American system (for tennis fans, you can read about the strategy here) with the explicit goal of becoming a leading tennis nation as demonstrated by winning Canada’s first Grand Slam singles championship and Canada’s first Davis or BJK Cup. It was widely criticized as being delusional and unrealistic.

The Results

In 2019, Bianca Andreescu won Canada its first Grand Slam singles championship by winning the US Open. Then in 2022, as mentioned above, Canada won its first Davis Cup (in its 109th try!). In addition, Canada has had three other Grand Slam singles finalists and made into the Davis Cup finals in 2019 — a foreshadowing of 2022 as it turned out.

Canada’s improbable success under the 2005 strategy caused American tennis legend and lead TV commentator John McEnroe to ask during a 2014 Wimbledon telecast: “Who would have thought Canada would become a tennis superpower?” The real answer to that question was only Tennis Canada leadership.

However, Canada has truly become a tennis superpower. Its young players are the envy of the world — except perhaps the US. There are currently two dozen players of age 23 or younger in the combined rankings of the top 50 men and top 50 women. Of those, the US has five, Canada has four (Bianca Andreescu — career high #4, Felix Auger-Aliassime CH#6, Denis Shapovalov CH#10, and Leylah Fernandez CH#13) and no other country has more than two (Spain, Italy and China).

How to Stick with Your Strategy

It took 17 years to accomplish both goals, and 14 years for the first goal. The first time we could say we were even close was the fabled 2014 Wimbledon at which McEnroe was commenting on our first male semifinalist of all time, Milos Raonic and our first finalist of either sex, Eugenie Bouchard: that was 9 years in. How can an organization stick to its strategy when it must wait a decade for clear sign that the strategy might produce the targeted outcomes and a decade and a half for the targets to be hit? And how can it make sure that it is not sticking to a losing strategy long after it should have been abandoned? I think there are four things you can do ‘to know when to hold ’em and know when to fold ‘em’.

Have a Clear Strategy

If you don’t have a clear strategy, it is impossible to evaluate what is happening in the world relative to what you are doing. For this I channel the great American philosopher Yogi Berra who opined: “You’ve got to be very careful if you don’t know where you’re going, because you might not get there.” Your strategy is a theory. You have a Where-to-Play, How-to-Win, Must-Have Capabilities, and Enabling Management Systems that you have designed to generate a given Winning Aspiration. It helps provide confidence in sticking to your strategy by seeing that your theory is being borne out by the emerging data.

For example, at Tennis Canada, we had a theory that held that in a small country (by population not geography — and the huge geography was a significant problem), we would get a greater number of talented athletes to take up and stick with tennis if we regulated outputs rather than inputs. That is, we have a residential National Tennis Centre, but if you want to train separately, and you demonstrate that you meet development standards including fitness, strength, skill development, etc., we will still fund your development.

We gained confidence with the theory as we saw Denis develop outside the system, Milos in a hybrid mode, and Felix entirely within the system. If we hadn’t had a clear theory, we couldn’t have assessed its effectiveness along the way, and that would have made it harder to stick to the strategy.

Leverage Your What Would Have to be True (WWHTBT)

But you can go further still in testing the logic of your theory to maintain confidence. If you develop strategy thoroughly, you will have a WWHTBT for chosen strategy. I argue that WWHTBT is the most valuable question in strategy because it helps a leadership team lay out concretely the full logic of its strategy, including the various elements that would have to be true for the strategy choice to be a good one. It is handy because after you have made your strategy choice you can routinely check on the elements that you felt would have to be true to see whether they still appear to be true. If they are, it will build your confidence. If, on the other hand, some aren’t, then you will have early warning that you should be modifying or abandoning your strategy.

For Tennis Canada a key WWHTBT was that we could elevate the profitability of the two top tier tournaments that we owned (one women’s/WTA and one men’s/ATP) to provide sufficient cash flow to get us out of debt and fund high-performance tennis development to the level contemplated in the strategy. Another was that we could attract international world-class coaches to work for us to raise the bar on coaching in Canada. Both WWHTBT were shown to be obviously true in the first five years of the strategy, helping us to remain confident in the strategy.

Patiently Watch for Green Shoots

Before the goals come clearly in sight, there can often be green shoots — very early indications that your crop may eventually bear fruit. Watch carefully and patiently for them and take great heart when you see them poke up out of what might appear to be barren ground.

Our green shoots were the Grand Slam junior tournaments for players 18 and under. Before 2005, a Canadian had never won a Grand Slam junior singles title. But in 2012, seven years into the strategy, Filip Peliwo and Eugenie Bouchard both won their respective junior titles at Wimbledon. Those were our confidence-building green shoots. They were followed by the senior results at the 2014 Wimbledon mentioned above and then junior wins in 2016 by Denis at Wimbledon and Felix at the US Open, and in 2019 at the French Open by Leylah.

But already by 2016, there was no doubt in our minds that this crop of players was going to bear fruit!

Defend It Against Self-Defeating Slippage

The final way to enhance your ability to stick to a strategy long enough for it to produce the desired outcomes is to defend it against slippage that will undermine it and in doing so cause you to give up on it. This is a case of external vigilance being the price of freedom! A strategy is always a delicate and precise thing. There will always be people in the organization that don’t appreciate the importance of hewing assiduously to every element of the strategy.

At Tennis Canada, this was a key role for the three successive Chairs of the Board (Jack Graham then Tony Eames then me) who for the first nine years of the strategy fought off every attempt to deviate from it. There were multiple attempts by good-hearted staffers to give monetary support to players who were used to training to lower standards and weren’t interested in or capable of contributing to the achievement of the goals of the strategy. If we had unlimited resources, that would have been ok. But we had extremely limited funding — a fraction of the level of the leading tennis nations — and it needed to be focused on the players who trained in a fashion consistent with winning on the world stage. By the end of the cumulative term of these three Chairs, the Tennis Canada strategy was out of the danger zone for self-defeating slippage.

Practitioner Insights

In life, one of the trickiest things to deal with is the delay between cause and effect. Nowhere is that more evident than in strategy. With the right strategy, anything is possible, no matter how inconceivable observers may opine that it is. But you must stick with your strategy long enough for it to bear fruit. As the super-successful Tennis Canada strategy demonstrates, sometimes that requires a lot of faith and plenty of patience.

Make sure that you have a clear theory behind your strategy so that you can compare what transpires to the theory to see if the theory is being confirmed or undermined. And use the WWHTBT that you generated in the process of creating strategy to check the degree to which the things that would need to be true are getting more or less true over time. Don’t let anyone undermine your strategy by chipping away at it — defend it until you stop believing that it is right. And watch for the green shoots. When they grow out of the barren soil, they will give you lots of confidence to keep pressing forward.



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.