Playing To Win

Another Year of Strategy

A Playing to Win/Practitioner Insights Year II Retrospective

Roger Martin
8 min readOct 31, 2022


Source: Roger L. Martin, 2022

When, in early fall of 2020, a client asked me for advice on how to think about the fifth box in my Strategy Choice Cascade, I decided to answer it by writing a Medium piece called The Role of Management Systems in Strategy. My client was appreciative, and many other readers liked it. I enjoyed their commentary and questions, so I kept writing, establishing a weekly rhythm and publishing one Playing to Win/Practitioner Insights (PTW/PI) piece every Monday morning for 52 consecutive weeks from October 5, 2020 to September 27, 2021. The following week, I published a retrospective: A Year of Strategy. Then I took three weeks off from PTW/PI, and then started again, publishing for another 52 consecutive weeks from November 1, 2021 to October 24, 2022. Now I am publishing Another Year of Strategy: A Playing to Win/Practitioner Insights Year II Retrospective. You can find the previous 105 PTW/PI here.

The PTW/PI series has garnered over 700K views and 120K followers. The articles total 180K words, more than two and a half times the original Playing to Win book’s 67K words. It has been fun, especially responding to reader questions. I always welcome ‘what about X’ and ‘how should I think about Y’ questions and try to respond to as many of them as I can.

As I did with Year I, I am providing a recap of Year II (below) today. Then, over the next five weeks, I am going to count down the five most viewed Years I & II articles, starting with #5 and finishing with #1, along with commentary as to why I think each resonated to such a great extent with readers.

And then, I will start into Year III of PTW/PI!

A Recap of Another Year of Strategy

1) The Role of Industry in Strategy

The job is to understand your industry so that you can encourage the evolution of your industry in a way that benefits your strategy.

2) Strategy and [Re]Organization

Reorganizations can’t make organizational walls disappear. They can only move walls to new places. So, think carefully about to where you will move them or else the unintended consequences of reorganization will be worse than the problems you are trying to solve.

3) Stop Letting OKRs Masquerade as Strategy

This one raised plenty of hackles. I argued for limits on the use of OKRs. That turns out to be an outrageous thought for many OKR fans.

4) The Secret to Knitting Strategy Together Corporate-Wide

To build a strategy corporate-wide, you need to start at its coalfaces — where customers decide whether or not to buy your offer — and build up from there, not down from the top.

5) Singing the Data Analytics Blues

Beware of hypothesis free data mining, complexity that overwhelms data analytics, and the inability of data analytics to predict the future.

6) The Lost Art of Strategy

Why and how strategy became a lost art in modern business, and what I am trying to do to fix that fundamental problem.

7) How to Make Your Partnerships Strategic

A partnership enables both parties to facilitate mutually desirable strategic outcomes. Otherwise, it is not a real or sustainable partnership.

8) Is Strategy a Zero-Sum Game?

It is only a zero-sum game when you accept the economist’s view of Where-to-Play. Seek out a distinctive Where-to-Play and you can encourage and promote winning for multiple players, to the benefit of both competitors and customers.

9) Competing Against Big New Entrants

Reverse-engineer the strategy of big new entrants to determine whether to up your game and fight, adopt key features of their strategy, or exit.

10) Business Strategy and/or Military Strategy?

There is much to take from military strategy that is useful in business strategy. However, its core principles must be modified not imported whole.

11) Strategy in High-Growth Industries

Recognize that high growth is a transient phenomenon. Make sure to think ahead about positioning in the end-game, and, in the meantime, be vary of overvalued equity.

12) Don’t Let Them Compel You to be Stupid

How to avoid the inevitable problems of overvalued equity, which is always a threat to encourage you to make stupid decisions.

13) Strategy for Startups

Yes, startups do have time for strategy. Plus doing the thinking behind strategy gives them the best opportunity to learn and improve.

14) The Impossibility Theorem

Take care to avoid creating a situation in which there is no overlap between people with the requisite capabilities for the job and people willing to accept the job.

15) Are You Building a Strategy Tower of Babel?

To avoid becoming a modern Tower of Babel, it is critical to standardize on a single language system for strategy — regardless of which one you choose.

16) The Great Resignation Should be No Surprise

The Great Resignation should be seen as a logical consequence of the breaking of a habit — working at the office.

17) What End of Advantage?

While the end of competitive advantage is a cool-sounding slogan, the opposite is happening in modern business as advantage is becoming more entrenched.

18) How to Get Buy-in for Your Strategy

Don’t attempt to achieve buy-in. Build commitment into strategy during its creation.

19) Corporate vs. Business Unit Strategy

Start with the indivisible level and aggregate in a way that builds reinforcing rods across businesses.

20) Understanding the True Building Blocks of Corporate Strategy

The fundamental building block of corporate strategy, the country/offering combination.

21) Who Owns Whom?

Take great care to ensure that you own your models rather than your models owning you.

22) Exploiting Analogy

Always ask: How might I apply the learnings from another situation to my situation? That will help you exploit the full power of analogy.

23) Strategy, Disruption & You

Technocrats tend to be shattered by the power of disruption. Instead, be a strategist and learn from disruption to build a better strategy.

24) The Presumption of Guilt

The presumption of guilt kills innovation. Utilize the presumption of innocence to give innovation a chance.

25) Talent Strategy in 2022

Stop trying to fit people into organizational boxes. Instead design organizational boxes to fit people.

26) Corporate Purpose & Strategy

Only if your corporate purpose drives selection bias, in employees, customers, and capital providers, that is helpful to your strategy is a useful corporate purpose.

27) Getting It Done

Work on developing your skills in Choice Chartering and then utilize the tool consistently in order to get things done.

28) Strategic Breadcrumb Spacing

Familiarity is extremely important to the subconscious, which is critical in driving behavior. When changing something familiar, changing it slowly to avoid shocking the subconscious.

29) Information Technology & Strategy

The three rules of flattening information technologies (IT) and the three ways to align strategy with IT.

30) The Design School Advantage

If you want to learn tools and techniques for analyzing and optimizing what is, go to business school. If you want to learn tools and techniques for creating what does not now exist, go to design school.

31) Organizational Strategy & Job Titles

The modern decision factory should organize around timebound projects, not unchanging jobs, and titles should reflect the projects for which each person is responsible.

32) How to Prevent Data Analytics from Wrecking Your Strategy

Don’t limit the data sources for inferences; don’t flatten data into its most unidimensional form; and don’t be convinced by data that something is undoable. Otherwise, data analytics will wreck your strategy.

33) Sustainability Strategy

How to use The Virtue Matrix tool to create a sustainability strategy.

34) Small is Beautiful

Why it is important in the modern era to pay serious attention to small and medium sized customers and be more careful about your economics in serving large customers.

35) A Management System for Forgiveness

The five characteristics of a management system for forgiveness that will minimize the destructive organizational impact of cover-up.

36) How to Compel Customer Action

Planning focuses on the independent variables that the company controls, while strategy focuses on the key dependent variable — the customer — which the company doesn’t control. That is why its strategy must focus on compelling to customers to take desired action.

37) My Love/Hate Relationship with VUCA

It has always felt that the world is more VUCA in the present than it was in the past. But that is an illusion because the past is always more resolved than the present.

38) Winning the Long Game of Strategy

Sometimes you have to take a step back and endure short term pain in order to win the long game of strategy.

39) Segmentation & Strategy

Segmentation is not deterministic; it’s probabilistic. You don’t determine customers’ segment; they do. Segments aren’t homogeneous; they are heterogeneous.

40) The Delusion of Single-Point Accountability

Single-point accountability is mainly a fantasy. Figuring out how to collaborate is more useful than fantasizing about single-point accountability.

41) Untangling Value Proposition & Competitive Advantage

Value Proposition is the value you produce for your target customers versus the cost of delivering it. Competitive Advantage is how to do it in a superior fashion to competitors.

42) What Makes for a Great Strategist?

The three mindset do’s and three mindset don’ts, plus the three skills necessary to be a great strategist.

43) What Would Have to be True?

Why What Would Have to be True (WWHTBT) is a more powerful question for strategy than the more common: What is True?

44) Why Planning Over Strategy?

Why Planning has triumphed over Strategy in the modern economy and the system that supports this damaging outcome.

45) Strategy for Generating Trial

How to generate valuable trial with a promise that minimizes monetary, temporal, and emotional friction for the target customer.

46) Quiet Quitting & Strategy

Understanding the role of abstract purpose, simpleminded motivation, and unfair distribution of benefits in the Quiet Quitting phenomenon.

47) Becoming a Better Strategist

The three mindsets and the three skills that you need to practice in order to become a better strategist.

48) Shutting Down Losers

How to overcome the shared economics argument in order to shut down losers that shouldn’t be allowed to continue to hurt the overall performance of the company.

49) Owner Economics & Strategy

How to think conceptually about the oft used but fallacious ‘owner economics’ argument that underpinned disastrous acquisitions including AOL/Time Warner and AT&T/Time Warner.

50) Strategy & Sunshine

Remember that the sunshine on your face creates a shadow behind you. In strategy, that makes it important to always consider the shadows that your successful strategy inevitably casts.

51) The Precision Modern Company

The goal of the modern company is to place each activity with an organization in which the jobs involved are critical to their competitive advantage. Talent will produce at its best when it is in a place that values their talent at the highest level.

52) My Least Favorite Business Book of All Time

Why Execution: The Discipline of Getting Things Done by Larry Bossidy and Ram Charan is my least favorite business book of all time.


Hope this overview helps you go back to find PTW/PI pieces that address questions or issues that you have.

And thanks for spending Another Year of Strategy with me.



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.