The “Playing to Win” Framework — A Global Strategy Expert’s Proven Method

What people typically think of when we talk about “strategy.” The second battle of Libya. Before zero hour. Brigadier commanding tank units in Tobruk instructing tank commanders on operations. British Army, Public domain, via Wikimedia Commons.

Introducing a simple, human-centered & accessible way to win

Ultimately, it always comes down to strategy

After two years of teaching, coaching, writing, and appearing on podcasts related to my knowledge of Objectives and Key Results, together with two OKR coaching certifications, it became clear that OKRs are one of the most powerful ways to deploy strategy.

To truly be effective at coaching across the organization with teams, product managers, and leadership to make the most of their limited time and resources and deliver the best results, I would have to make strategy part of my skill set.

Unfortunately, the conventional approach to business strategy is both deeply misunderstood and overly complex.

How Business Strategy is typically practiced

Strategy has always been treated as an area reserved for people with better academic credentials and “bigger” brains.

Boston Consulting Group founded the modern business strategy practice, borrowing concepts from military strategy.

Over time, other consultancies started to offer and grow their strategy consulting services.

At the same time, business schools broadened their strategy offerings, approaching it mostly as an analytical exercise, studying how past models of strategy could be learned and applied.

This analytical approach to strategy logically leads to hiring one of the global strategy consulting firms to crunch data, analyze it, and dream up a brilliant strategy and hand it off to subordinates for “execution” in a 500-page PowerPoint slide deck.

Any failure of the organization in the wake of this strategy is purely due to the inability of the “do-ers” to execute against the “thinkers’” brilliant plan.

But this isn’t a strategy, it’s at best a set of initiatives, and at worst, “a strategic plan.”

From Dilbert by Scott Adams. All rights reserved.

A new way to think about strategy

Yet for Roger L. Martin, strategy and planning are fundamentally opposed — true strategy is not a plan, but a set of choices.

“…strategy is choice. Strategy is not a long planning document; it is a set of interrelated and powerful choices that positions the organization to win.

Roger L. Martin

Meet Roger L. Martin

Roger Martin has probably had more consistent success with strategy over a longer period of time than anyone.

As a principal at the Monitor group, followed by an engagement as Procter & Gamble CEO A.G. Lafley’s personal strategy coach during Lafley’s leadership of P&G, the company had an unprecedented string of hits associated with many products we know and use every day.

In 2013, Roger Martin collaborated with Lafley to capture their successful strategy framework in their book “Playing to Win,” which formalized their “Strategic Choice Cascade” strategy framework.

Just a few of Roger Martin’s Strategy Successes

Beyond his success with P&G, Roger Martin is also a deep thinker, innovator, and academic, and a strategy practitioner who’s repeatedly achieved success applying his framework across a wide variety of industries.

The Rotman School of Business

As newly-elected dean of the Rotman School of Management, Martin applied his strategic approach to take an underperforming Toronto business school to among the top MBA programs in the world.

The Toronto Film Festival

Through Roger’s strategy consulting, The Toronto Film Festival went from an “also-ran” event to international prominence as a place to premier new films that have achieved not only critical acclaim, but global box-office success, in direct contrast to the Cannes Film Festival.

Tennis Canada

Near and dear to my own interests, Roger equally applied his strategy framework to the challenge of improving the standing of Canadian tennis.

Through Martin’s guidance applying his framework to a set of strategic choices, tennis in Canada has gone from an inconsequential “blip” on the world tennis scene to consistent international success, going from no players in the female & male top-50 rankings to having two in the top 10.

And it continues…

Roger Martin has had, and continues to have, numerous other strategy consulting successes with LEGO, Ford Motors, and many, many more prestigious organizations.

But for all his success, Roger Martin’s goal has been to make strategy human-centered and accessible to all.


Initially coming to prominence as a design firm, IDEO has since broadened in a number of areas including education and training through IDEO U.

Aside from offering perhaps one of the premiere Design Thinking certificates, IDEO U has partnered with Roger Martin to create the Designing Strategy course, an online cohort-based offering which offers a methodical approach to make the most of the “Playing to Win” framework.

And, not coincidentally, Roger Martin’s Designing Strategy course co-instructor is none other than Jennifer Riel, IDEO’s Global Head of Strategy.

A Design Thinking Approach to Strategy

What makes IDEO’s approach to strategy, together with Roger Martin and Jennifer Riel, unique?

In a radical departure from the conventional analytical business strategy approach noted above, the “Playing to Win” framework takes a creative approach deeply rooted in Design Thinking.

As noted above, the conventional business strategy approach as practiced throughout most organizations is based on conventional Analysis and Planning, and it’s predominantly the kind of strategy businesses buy when they hire one of the big global strategic consulting firms.

But for Roger Martin, strategy is fundamentally a creative act, focused as it is on designing that which has not yet existed. Conventional research-based and data-crunching analytical approaches can only tell you what has happened in the past — they aren’t well suited to innovating in the service of creating an alternate future.

What makes the Playing to Win strategy framework unique is that it neither over-indexes on Creativity, nor Analysis, but skillfully weaves back and forth between Divergent and Convergent thinking modes to achieve creative innovationtempered by scientific hypothesis and testing rigor.

A Plan is Not a Strategy

Get ready to have your ideas about strategy and planning massively shifted in less than 10 minutes through this Harvard Business Review video, where Roger Martin clearly lays out the difference between an analysis, planning & internal focus in direct opposition to a creative, strategy, and client-centric approach.

How can you learn and apply this approach to your work?

Enter the “Playing to Win” strategic framework as taught through the “Designing Strategy” course at IDEO U.

The “Playing to Win” Strategy Framework

The “Playing to Win” framework consists of two key pieces:

  • The Strategy Process Map
  • The Strategy Choice Cascade

Each component has been tested and refined to create the creativity and rigor critical to the success of the framework.

The Strategy Process Map

From Strategic Planning: How to Get Started

The Strategy Process Map consists of 7 steps:

  1. Identify the problem
  2. Frame a strategic question
  3. Generate possibilities
  4. Think about what would have to be true
  5. Understand barriers
  6. Conduct tests
  7. Choose a strategic direction

Each step has been crafted to go from clarifying a deep-seated problem plaguing ones’ business, to making a set of choices that will best position the firm to win.

The Strategy Choice Cascade

From A.G. Lafley “A Cascade of Choices

Roger Martin has been using the Strategy Choice Cascade for decades, and these five simple questions form the core of creating a great strategy.

  1. What is our Winning Aspiration?
  2. Where will we Play?
  3. How will we win where we have chosen to play?
  4. Capabilities — The reality check for the How to Win — What decisive capabilities will we need?
  5. Management Systems — What infrastructure, systems, processes, and metrics will we need to support and measure our strategy over time?

Deeply reviewing each of these questions together so the answers provide an integrated set of choices will provide a powerful step in forming the foundation of a different future.


Over the next two articles, I’ll dig more deeply into the Strategy Process Map and the Strategy Choice Cascade, and offer practical examples how this powerful framework works and how you can apply it based on my experience taking the IDEO U “Designing Strategy” course, and subsequent research.

This is Part I in a series.

Part II, on the Strategy Process Map, is here

Part III, on the Strategy Choice Cascade, is here

Check out these related resources:

The IDEO U Designing Strategy Course

The IDEO U Designing Strategy course is among the best online, cohort-based courses I’ve had the fortune to take.

It’s not inexpensive, and represents a minimum four-hour time commitment of homework per week for five weeks, but as with most things in life, you’ll get out of it what you put into it.

Any extra time you can put in studying, completing the coursework, and attending the online Zoom cohort meetings will allow you to come away, as I feel I have, tremendously enriched and with a strong working knowledge of the fundamentals of a human-centered, proven approach to designing winning strategies.

You may be as surprised as I was how much of the subtleties of applying Design Thinking and rigor to strategy were deepened as a result of the course’s supplemental material, exercises, meetings, and additional readings.

More info on the course

Designing Strategy Course Overview

How to Create Winning Strategies — blog post & podcast with Roger Martin

Strategic Planning: How to Get Started — blog post & podcast with Roger Martin

Jennifer Riel

More info on Roger Martin

Roger Martin on Medium (no stories are behind the Medium paywall!)

Strategy and Design Thinking

Roger Martin Podcasts & Videos

Roger Martin on Harvard Business Review

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