When Going in New Directions, It Helps to Have a Map

Play to Win Strategy Canvas

I developed the Play-to-Win Canvas, a large wall map, to help teams explore strategic possibilities. (Click HERE to download a full size PDF, or HERE for a personal A3 size, both sharable under a Creative Commons license.)

So, you’ve decided you need to shift strategy. You’ve drafted your current strategy using the Roger Martin Playing to Win five-question strategic question cascade (What’s Our Winning Aspiration? Where do we play? How do we win? What capabilities do we need? What systems are required?) You’ve defined the most worrisome problem or strategic issue, and you’ve reframed it as a choice between at least two mutually exclusive options. You’ve expanded each choice and brainstormed initial where-to-play/how-to-win combinations. You’ve clustered them by theme. You’ve culled them so that you’re down to three or four thematic possibilities.

Now it’s time to generate a strategic cascade for each of those possibilities. And this is where the canvas helps. By watching and working with teams over the past two years, and picking Roger Martin’s brain, it became very clear to me why producing a new winning strategy is difficult: people like to lock and load on a given direction far too early in the process. They don’t challenge the status quo enough. They don’t push their thinking.

In other words, there’s a great temptation to take a single initial strategic possibility and develop a full strategy around it. Wrong move. You need to basically start over, with that possibility as simply the point of departure.

So, for example, and to continue with our hypothetical company STAR FITNESS TRAINING (see this post), they have identified a strategic issue, and have three initial where-to-play/how-to-win possibilities they believe are worth exploring:

  1. expand to all of Southern California through franchising
  2. expand into less affluent client segment by hiring, training, and certifying new training associates, and
  3. offering exercise DVD products.

So far so good, but the whole reason I developed the Play-to-Win canvas is because I see how tempting it is to cherry-pick one of the three, get the heads in the room nodding in agreement, and go from there. If you do that, all you’ve really done is to shortchange the art of possibility by two-thirds! (Actually, more, if you include the current strategy as a possibility).


For each of the three new possibilities, you want to start from the top: What’s our winning aspiration? Where will we play? How will we win? What capabilities are required? What management systems must we have?

I have found it very difficult for a strategic team to create robust cascades for more than one possibility, so I like to split the larger group up into smaller exploratory units, each devoting their entire attention to one possibility.

Here’s the good news: the canvas is self-guided, and self-contained. It has definitions, prompts, and tips. It even guides you in teasing out assumptions (“What would have to be true for these choices be successful?”) and crafting an experiment to test those assumptions.

Once the canvas has been completed (and this could easily take days) for each of the strategic possibilities, you can stand back and decide which one you’d like to start with in terms of testing the strategy. (Hint: Do NOT test out all possible strategies at the same time. Start with the one everyone is leaning toward.)

Remember, the Play-to-Win Canvas is just a tool for fleshing out strategic choices. It’s an artifact of your best thinking. A starting point. A strategic story.

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Matthew E MayMatthew E. May is the author, most recently, of Winning the Brain Game: Fixing the 7 Fatal Flaws of Thinking.

Matthew E May




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  1. Braden Kelley on August 10, 2017 at 3:26 pm

    Matt just published an updated version of the canvas which you can find here:


    Thanks Matt!

    • Tobias on January 12, 2021 at 2:30 pm

      Is there a current version that can be accessed somehow? Love the content!

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