We have reached the end of Year V for the Playing to Win/Practitioner Insights (PTW/PI) series. The appetite for PTW/PI pieces continues to amaze me. I would have never imagined it when I posted my first piece in the series on October 5, 2020. That is a bit more than five years ago (thanks to year-end summaries/commentaries in between). You can find all the previous PTW/PI here.
As I did with Years I through IV, I am providing a recap of Year V today.
A Recap of Still Another Year of Strategy
Strategists need to add a third lens to the economic lens and the user lens — the world lens that sees customers as members of communities, not as only individuals.
The current tension over tariffs is part of a wider realignment in the world political, economic and military order by which the post-World War II favoring of small nations over large is being reversed.
There are five different kinds of substitution that a company can face, and each has its own unique strategic implications.
4 ) Starbucks & Strategic Entropy
Starbucks recent challenge represents a classic case of strategic entropy, driven by both offensive and defensive forces. A good strategy protects energy rather than allow it to dissipate.
5 ) Management Tasks, Responsibilities, Practices & Playing to Win
In this classic, Peter Drucker provides a worker-centric view of companies and a view that is highly compatible with Playing to Win — in particular that strategy is an integrative tool.
6 ) Developing a Powerful How-to-Win
To develop a powerful How-to-Win, think about it as a portrait in which all the parts of it fit together and reinforce each other to tell a powerful story.
7 ) Will Artificial Intelligence Eradicate Practitioners of Strategy?
Yes and no. It will eradicate strategy tasks that seek the most common answer — and that may well be 50% of strategy jobs. But it won’t be able to develop unique solutions because it has no way to look for them.
8 ) Playing to Win & Regional Strategy
Playing to Win can and should be applied to strategy for geographic regions. All five of the questions pertain to regional strategy and the cleverest regions, like the Maldives, have clear — and successful — strategies.
There isn’t a big overlap between the Big 5 Personality Types or Myers-Briggs Type Indicator and strategy capability. There is a bigger overlap with Carol Dweck’s growth mindset and Angela Duckworth’s concept of grit.
10) Stop Working for Loser Strategists
Working for an incompetent strategist is deadly for your effectiveness. If you are, give it no more than two years of trying to remedy the situation before exiting in search of a better situation.
11) The Myth of Objectivity & Strategy
The obsession with bringing science into the non-scientific field of business has produced the myth of objectivity which produces damaging polarization and crappy decisions.
12) Dealing with Intuitive, Non-Strategists
Don’t despair because you think that a person not dedicated to analysis and suspicious of strategy won’t make strategic choices. Fix their most pressing problem and they will embrace strategy, even if you don’t call it that.
13) Training a Novice Strategist
The best thing you can do is help them shift four mindsets: 1) from formulating strategy to facilitating strategy; 2) from getting buy-in to generating internal commitment; 3) from crunching data to clarifying logic; and 4) from applying dueling frameworks to building an agglomerative model
14) Integrating Strategy with Planning & Budgeting Processes
Strategy needs to be proactively integrated into planning and budgeting processes because the latter processes will happen whether there is explicit strategy or not.
15) Generating Creative Strategy Possibilities
The three best tools for generating creative strategy possibilities are to: 1) apply analogies; 2) tackle perceived trade-offs; and 3) pay attention to anomalies.
16) The Trickiness of University Strategy
When they consider strategy, universities need to understand that they operate as a platform for multiple two-sided markets — an educational two-sided market and a research two-sided market. The trick is in devising a strategy that succeeds in both.
When thinking about Where-to-Play, an important feature is to consider the degree to which you want to choose a thin slice of value (e.g. the Android operating system) or a thick slice (e.g. the iPhone integrated hardware/software/app store solution).
To improve the likelihood that innovative change will be accepted make sure that the team reverse-engineers (using the What Would Have to be True tool) both the status quo and the innovative alternative so that it recognizes both have inherent risks, not just the innovative alternative.
19) Influenceability, Society & Strategy
Being influenceable is a prerequisite for being a useful member of society or a business team. If you aren’t influenceable, it is better if you are alone.
20) The Evolution of the Strategic Choice Structuring Process
I have just issued the fourth generation of the Strategic Choice Structuring Process, which has evolved over the past three decades as I have watched clients use it.
21) The Writing vs. Editing Distinction
A useful way to think about management is that their role is that of writers while boards just take on the role of editors. Problems ensue when boards take on the writing role.
22) Going on the Offensive with Creative Strategy
To innovate in the modern economy, you must accept that you can’t defend innovation. Rather you need to go on offensive against the idea that a continuation of the status quo is less risky than a well-considered innovative path.
23) Strategy, Artificial Intelligence & Entry Level Hires
The companies that are slashing entry level hiring because of artificial intelligence (AI) are making a major intervention into a complex adaptive system — their company — without having any idea of the effect, whether good, bad or indifferent.
24) Misplaced Shoulds in Strategy
People tend to want a lot of ‘should’ rules for strategy. I have few. But the most important should is that strategy should start from the reality of where we are today, not some idealized abstraction of what ‘should’ be.
25) Strategy & Non-Financial KPIs
Non-Financial KPIs are important for measuring strategy and making course corrections as necessary and the way to create them is to be guided by the What Would Have to be True that you created for the chosen strategy.
26) How I Do Strategy — Part One
These are the first two steps of the four-step process I use when I create a strategy for an organization that I lead.
27) How I Do Strategy — Part Two
These are the final two steps of the four-step process I use when I create a strategy for an organization that I lead.
28) Strategy for Organizations Without Competition
Why Playing to Win is applicable for strategy for government agencies, even though they have no direct competition.
29) Strategy & Your Investor Relations Organization
When it comes to making bold strategy choices, your Investor Relations organization won’t automatically be on side — unless you pay clear attention to it.
30) The Future of the Middle Class Depends on Frontline Service Jobs
Executives have a strategic choice whether to see their service workers as a frontline burden or frontline engine — only with the latter will the middle class in America prosper
Many executives have interpreted emergent strategy as a motivation/excuse for strategic nihilism. Sadly, it is both delusional and destructive — to be avoided.
Strategy work tends to be unhelpfully shallow because it uses faux science, which forces shallow analysis of a wide variety of topics rather than deep analysis of a critical few.
33) Technocrats vs. Strategists
CEOs operate along a spectrum from technocrat to strategists. The former creates limitations while the latter enables possibilities.
34) A Primer on Strategy Choice Chartering
In order to make strategy and action happen throughout a whole company, managers at every level need to thoroughly charter strategy choices and here are three concrete examples.
35) Revisiting my Definition of Strategy
After a quarter-century with my longstanding definition, I have updated my definition of strategy to focus it more on what is really important: compelling desired customer action.
Functions all have strategies whether explicit or not. What they do and do not do defines their strategy, and it is much better to make explicit conscious choices than just slide into a random set of actions.
37) The Future[s] of Business Education
There is a fundamental schism in business education by which it teaches two things that can’t coexist in business — that a valid inference requires a representative sample and students must always make rigorous, data-based decisions.
Culture change is difficult, and the proposed solutions are typically ‘wholesale.’ Changing interpersonal interactions is the key to culture change and the only way to accomplish that is with a ‘retail’ mindset.
39) Why the How-to-Win Strategy Choice is So Hard
The How-to-Win choice is hardest because the upstream choices are often flawed, it has the highest bar and there aren’t supportive systems. The key is to recognize it is hard, be patient and maintain the high bar of winning, not just playing.
40) What has Changed the Most for Strategy
Contrary to popular opinion, what has changed most is NOT increased VUCA. The two biggest changes for the context of strategy are fixed/variable cost mix and price/value discovery.
41) Something from Nothing Leaves Something
When you start with far fewer resources than competitors, don’t seek to emulate their unaffordable advantages, work, like Singapore did as a country, to find inexpensive sources of advantage that the well-resourced are unlikely to attempt to replicate.
42) Revisiting Management Systems
For the 250th piece in this series, I revisited the first in the series which was on the role of management systems in strategy. The way to think about the Enabling Management Systems box in the Strategy Choice Cascade is that it is the nervous system for strategy.
43) Diversification Can’t Disappear a Strategy Problem
A logical fallacy drives much unsuccessful diversification by way of acquisition. The motivation is to diversify away from a shareholder-unfriendly part of the portfolio. Sadly, it fixes nothing while creating more challenges.
44) A Leader’s Role in Fostering AI Superpowers
Everybody uses and worries about AI. To help AI have a productive impact on business and society, leaders need to master the five levels of augmentation through AI.
45) Thinking Intelligently about Corporate Purpose
Having a lofty corporate purpose doesn’t help make the world a better place unless it is seamlessly integrated with the other four strategy choices.
46) The Strategic Logic of the Netflix-Warner Bros. Deal
Unlike the previous AOL and AT&T acquisitions of the Warner assets, the Netflix deal makes strategic sense. But regulators need to look closely at its antitrust impacts.
47) Strategy & Connoisseurship
To become a great strategist, you need to build your connoisseurship in a similar fashion to the way in which sommeliers build theirs.
48) The Hidden Where-to-Play Element in Strategy
The fifth and largely hidden or implicit element of Where-to-Play is value system stage. To have a great strategy, this element of strategy choice must be made explicitly.
49) Strategy & Opportunistic Hold-Up
Valuable companies (and individuals) attract guileful actors who attempt to extract value from them through opportunistic hold-up. Guarding against it is a key element of a sustainable strategy.
David Kantor provides a useful model for strategists to understand themselves and the terms with which they work. There are three Heroic Modes, fixer, survivor, and protector that shape our behavior.
51) Becoming an Effective Strategy-Led CEO Advisor
Effective Strategy-Led CEO Advisor is the third step in a journey beginning with Strategist. Getting to the pinnacle requires curiosity, patience, honesty — and a lot of determination.
52) Fixing Strategy
Strategy is broken and needs fixing. The are five elements to fixing strategy, which needs to be performed by general managers, driven by imagination, guided by principles, iterative and distributed.



Thanks Alex. It is helpful for me to hear what are the most important takeaways for readers - especially engaged ones like you. Best, R
Thanks Netsanat. I will think about that is something to potentially do on Substack.