Playing to Win

A Year of Strategy

A Playing to Win/Practitioner Insights Retrospective

Roger Martin
8 min readOct 4, 2021


Copyright: Roger L. Martin, 2021

It all started innocently. I was getting frustrated with how long it took to get quick hit writing out. For what are hoped to be timeless pieces for the print edition of Harvard Business Review, I don’t mind the one to three years it takes to get an article ready for publication. But I had a time-sensitive piece on COVID and strategy that I submitted to a faster-cycle publication (that shall remain nameless) in the summer of 2020 when companies were desperately trying to figure out how to navigate COVID. The editor liked it but told me that it would be at least three weeks until she would even look at a full draft.

I groused about that lackadaisical reaction to Jessica Krakoski, who was helping with the publicity of my fall 2020 book, When More is Not Better. She suggested that I experiment with writing for Medium because on that platform, the minute you have finished writing a piece, you can hit ‘publish’ and it is out there. I followed her suggestion (thanks Jessica!) and on July 23, 2020, published Habits, COVID & Strategy. I enjoyed my first Medium experience and wrote another nine pieces on a variety of subjects.

Then, in response to a client’s question, I wrote The Role of Management Systems in Strategy to provide practical advice on how to think about the fifth box in my Strategy Choice Cascade, and published it on October 5, 2020. The response was so overwhelming that I decided to write more pieces for Playing to Win enthusiasts who wanted tips on how to apply the framework in practice. The series built a momentum of its own and an increasingly large audience. I established a weekly rhythm and published one Playing to Win/Practitioner Insights (PTW/PI) piece every Monday morning for 52 consecutive weeks: A Year of Strategy.

I will first recap the year and then provide thoughts on where from here?

A Recap of A Year of Strategy

1) The Role of Management Systems in Strategy

The three important roles Management Systems can play in reinforcing strategy.

2) Is the Opposite of Your Choice Stupid on its Face?

You will know that you have made a strategy choice if the opposite is not stupid on its face.

3) Why I am Skeptical of Low Market Shares

If you think your market share is under 20%, you probably have defined the denominator too broadly.

4) Strategy is what you Do, not what you Say

It is more helpful to understand your strategy as what you do than what it says in any strategic plan, and therefore every organization has a strategy.

5) Strategy as Problem-Solving

Strategy is a technique for solving problems. If you don’t define a problem to be solved, your strategy exercise is likely to have limited value.

6) Strategic Choice Chartering

Strategy is created throughout the organization and hence the chartering of strategic choices is a very important leadership skill.

7) From Laudable List to How to Really Win

Much of strategy involves making lists of laudable things to do but that don’t add up to a winning strategy.

8) Strategy as a Practice

Strategy is a practice and that the only way to get good at strategy is to practice the practice.

9) Strategy & Time

You should do strategy when your What Would Have to be True is no longer true, not on some calendar cycle.

10) Playing to Win for Social Sector Organizations

How to apply Playing to Win to social sector organizations of all sorts.

11) Strategy & Design Thinking

How to integrate key Design Thinking attributes into the Playing to Win strategy process.

12) Strategy & Integrative Thinking

How key Integrative Thinking attributes can and should be integrated into the Playing to Win strategy process.

13) On the Inseparability of Where-to-Play and How-to-Win

Avoiding the trap of considering Where-to-Play and How-to-Win independently rather than in tandem.

14) The Trap of Presiding Over Strategy

Business leaders should not see their job as presiding over strategy but rather engaging deeply in strategy.

15) Is Strategy in B2B Dramatically Different than in B2C?

There are more similarities than differences between B2C and B2B strategy.

16) My Business is Too Fast-Moving for Strategy

It is both specious and dangerous to argue that your business is too fast-moving to do strategy.

17) Playing to Win and Scenario Planning

How to integrate Scenario Planning attributes into the Playing to Win strategy process.

18) Distinguishing How-to-Win from Capabilities in Your Strategy Choice

How to untangle Capabilities from How-to-Win and think about Capabilities in the Strategy Choice Cascade.

19) The Two Rules that Monopolists Ignore at Their Peril

This was the least successful of the 52 posts. Must not have felt sufficiently practitioner focused, but it identifies important watchouts for monopolies.

20) Strategy vs. Planning: Complements not Substitutes

The second most read post provides the key distinction between Strategy and Planning.

21) The Motivation for Strategy

Insights on the first box in the Strategy Choice Cascade — the Winning Aspiration.

22) The Tragic Futility of Investing to Catch Up

Investing to catch up competitively has much lower utility than investing to leapfrog competition in order to win.

23) The Role of Strategy in Achieving Managerial Effectiveness

Managerial effectiveness is aided by clear strategy, not independent of it.

24) Reliability versus Validity in Strategy

The implications for strategy of two opposing forces in business — producing a consistent replicable outcome and producing an outcome you would actually want.

25) Where’s the Business Model in Playing to Win?

Your business model is neither independent of nor fits in one box of the Strategy Choice Cascade but is a part of all five boxes.

26) The Shift from Pre-Competitive to Competitive

The dynamic by which industries shift from a pre-competitive state to a competitive state and implications for strategy.

27) Can You Be Both Cost Leader & Differentiator?

For short periods you can be both but in due course, competition will make you choose.

28) It’s Time to Toss SWOT Analysis in the Ashbin of Strategy History

The most controversial and widely read of the whole series. Many readers assured me that SWOT isn’t that bad — hardly an endorsement of the tool!

29) It’s Time to Accept that Marketing and Strategy are One Discipline

The second most controversial and third most read. Many readers explained that scholarship and current practice disagree with me. But my job is to fix faulty conventional wisdom, not bow to it!

30) Manipulation of Quantities & Appreciation of Qualities

The modern strategist needs these two skillsets, but modern education favors manipulation of quantities over appreciation of qualities.

31) Strategists: Stop Obsessing about Averages

Strategists pay too much attention to averages, which reinforce the status quo, rather than outliers, which give clues to where the future is leading.

32) What is Digital Strategy, Anyway?

There are three forms of digital strategy with differing potential for your overall strategy.

33) Overcoming the Pervasive Analytical Blunder of Strategists

The analytical blunder strategists make when they take data from the past to make inferences about the future.

34) Your Personal Playing to Win Strategy

The application of the Playing to Win strategy framework to your personal career.

35) From Strategy to Planning

How to productively link your planning to your strategy.

36) Asking Great Strategy Questions

The three classes of questions to review and test strategy; questions about logic, fit, and distinctiveness.

37) It’s Time to Accept that Pay for Performance Doesn’t Work

Pay for performance doesn’t help cause productive actions to be taken on strategy; in fact, it causes the opposite.

38) Playing to Win & Agile

How Agile principles can be integrated with the Playing to Win strategy process.

39) Balancing Exploration and Exploitation

In service of great strategy, one needs to balance exploration of things in which the organization is now not expert with exploitation of things in which the organization is expert.

40) The Delusion of Revenue Forecasting

Revenue forecasting is largely a waste of time because the decision to send revenues to the organization doing the forecasting is completely in customer hands.

41) It’s All About Confidence

Successful branding is all about building customer confidence.

42) Can your Strategy Pass its Most Important Test?

The most important test of your strategy is the can’t/won’t test: are you confident that competitors either can’t or won’t successfully replicate your strategy.

43) Playing to Win & Sales

The important role of sales in strategy and the underappreciation of sales in business school curricula.

44) Diversity & Strategy

Diversity of viewpoints is critical to great strategy and that to leverage that diversity, you need to utilize the Integrative Thinking toolbox.

45) Compelling Communication for Your Strategy

In communicating your strategy, less is more, and a picture is worth a thousand words.

46) The Proper Role of the Chief Strategy Officer

The proper role of the CSO is to: 1) facilitate the creation of strategy; 2) coordinate the creation of strategy; and 3) ensure the consistency of strategy.

47) Should We Listen to Customers?

The wrong question is whether we should listen to customers. Instead, it should be in what way we should match how we listen to customers with the strategic task at hand.

48) Strategy & Boards of Directors

Most management/board relationships are set up for disappointment. The key to success is a better when and a more nuanced what.

49) The Battle for the Soul of Strategy

The battle in strategy theory between the positioning school and the resource-based view of the firm is silly; we need to integrate aspects of both into a better strategy theory.

50) Strategy in the Face of Discontinuity

The important role that What Would Have to be True can play in helping you determine strategy in the face of discontinuity.

51) Strategy & Transformation

The four keys to transformation success: strategy, patience, resilience and growth.

52) Why do Strategy, Anyway?

The importance of engaging in strategy in order to learn faster than competitors so as to beat them.

Where From Here?

That is 85K words of PTW/PI, more than the original Playing to Win book’s 67K words. Two publishers have suggested publishing A Year of Strategy as a book — who would have known, publish it first for free, then as a book? I guess when you are at 256K views (and counting), that is evidence of an audience, so I will do that.

I am going to take a break on the weekly PTW/PIs. I plan to continue writing on Medium, but 1,500–2,000 words/week is a bit too taxing and has crowded out other writing — my HBR Senior Editor, David Champion, is still waiting for my next new magazine piece.

My plan is to get even more reader driven. Twenty of the 52 were motivated by reader questions, so readers have already played a big role (thanks!). But I welcome with open arms more ‘what about X/how should I think about Y’ questions. I am planning to broaden from the core Playing to Win theme, so other strategy and/or management questions are entirely welcome. I may do a number of miniseries (say 4–6 pieces rather than 52!) each around a particular theme and have had suggestions already that lend themselves to that format in that the answer has several distinct components and won’t fit into one sub-2000-word piece.

Thanks for spending A Year of Strategy with me and watch for my next Medium piece within a month.



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.