PTW/PI All-Stars Book Club – Chapter Six
The Lost Art of Strategy
Welcome to Chapter Six of the Playing to Win/Practitioner Insights (PTW/PI) book club. Again, in the spirit of a book club discussion, I have responded to all previous comments and will continue to do so. Of the 37 all-star pieces out of the 260 in the series, the randomizer picked The Lost Art of Strategy as the sixth chapter. This one is the second from the third biggest category – screeds – which I defined in Chapter Five. You can find the whole PTW/PI series here.
My Reflections on This Piece
The core reflection is that I wrote the original article five years ago and everything I discussed has gotten worse – sigh. But on to further thoughts…
I have a long history with strategy, a business discipline/practice that has been around since the foundation of Boston Consulting Group (BCG) in 1963. I started working in strategy in 1981, so I have been practicing strategy for 71% of its 63 years of existence.
I view the 1970s and 1980s as the heyday of strategy. In the 1960s, it was still emergent. But by the 1970s it had become big but was still new and exciting. And it was proprietary. Even by the end of the 1970s, there were few strategy courses or professors. For example, while I was an MBA at Harvard Business School in the 1979-1981 period, there was exactly one strategy course in the entire curriculum (Mike Porter’s second year elective).
But strategy built massively in the 1980s. It was a great time. BCG grew to global size and scale and was joined by spin-off Bain & Company in 1973, and Monitor Company opened shop in 1983 – all three of which primarily worked on strategy. McKinsey never did but tried hard to catch up by adding strategy to its longstanding practice areas.
However, the art and practice of strategy turned dramatically for the worse in the 1990s. There was a huge ramp up in strategy professors as strategy became the fastest growing discipline in the business academy in the 1990s. They made it a consequential academic discipline at business schools. However, along with that came a powerful lurch in the academic/theoretical direction. Suddenly there were academic strategy theoreticians everywhere. Don’t get me wrong. I always like a good theory. But like Karl Weick, I care about whether a theory is useful – or not so much. And most of this new crop of academic strategists didn’t care deeply about utility in the business world. And the defining feature of the strategy academy was jealousy of Mike Porter. They wanted strategy to be approved and owned by the academy, not shaped by a best-selling book.
In terms of the utility or lack thereof of formal strategy education, I remember that at Monitor, like the other ‘strategy consulting firms,’ we used to hire the best and brightest both out of elite undergraduate and MBA programs. But in the early 1990s, we concluded that a liberal arts undergrad from Williams or Swarthmore knew as much useful stuff about strategy as an MBA from HBS, Wharton or Stanford, and much to the dismay of the latter, we put the MBAs in the same intake training program as the liberal arts undergraduates and started them all from scratch on strategy. Suffice it to say, we weren’t at all sold on the value of academic strategy research and teaching.
And at the same time, ‘strategy firms’ stopped doing much strategy, as I discussed in detail last week, and instead started spending their time kiting best demonstrated practices around industries to converge their clients on doing the same thing as their competitors – hardly true strategy.
Now the proverbial ‘best and brightest’ mainly go into private equity. And the ones that go to the so-called ‘strategy consulting firms’ have been taught little useful about strategy at business school and then go on to get taught how to do digital transformation, overhead cost reduction, and post-merger integration.
As a result, there is no consistent source of strategists in the modern world and little development of strategists in it. I wish that wasn’t the case – but it is. It is truly becoming the lost art.
And as strategy has gone into decline, the great enemy of strategy, planning, has struck back. Planning was dominant all the way through the 1950s and 1960s. Technocrats like Robert McNamara, whiz kid and US Secretary of Defense during the central period of the Vietnam War, were the rock stars and their tool was planning. They planned so as to control the future – which sadly cooperated only rarely.
The failure of planning helped the original ascendency of strategy. But planning bided its time during the heyday of strategy and then reasserted itself. I have written plenty about the modern dominance of planning over strategy, so I won’t repeat it all. But if you are interested, see here, here, here, and here for my commentary. Planning is a comfortable and familiar thing. It is safe and easy. Strategy is hard to do in practice. For the latter, it is not sufficient to teach a bunch of analytical tools and believe that is enough. Strategy requires true choice, which is challenging and is why strategy is becoming the lost art.
Despite the wild enthusiasm for Artificial Intelligence (AI), which has exploded since I wrote The Lost Art of Strategy five years ago, I don’t see AI as restoring the lost art. As I have pointed out in a previous piece in this series, AI is a mode-seeking device. It doesn’t search for the unique. It searches for what is most frequent. In many respects, AI is benchmarking on steroids – and in strategy, benchmarking is for losers. There is no question to me that AI can be useful to experienced strategists, for example in assembling, crunching and displaying data, but it can’t turn a planner into a strategist.
One of the central goals of this PTW/PI series is to help strategy become less of a lost art by providing practical advice on how to really do strategy – with now over half a million words of free strategy content.
Reader Comments
As with last week’s screed, there were lots of positive comments on this one: “Everything you say here is absolutely true,” “I agree,” “Brilliant article” (x2), “Great article and great insight,” and “Awesome article! Well done!”
The dominant reaction to the piece was to point to the confusion over what strategy truly is. Many saw the vacuum of confusion about strategy enabling the rise of tacticians/planners. I think the commenters are right.
One reader observed that Agile is often used as “an excuse to have no strategy, do little to no market intelligence, and just randomly try a bunch of things.” I am not sure that is generally true, but I sometimes think that Agile aficionados like to put strategy and Agile in opposition. They aren’t inherently, as I have discussed before in this series.
The single most interesting reader comment was the following very accurate observation: “We are linear, goal-oriented organisms in a cyclical, circular, reciprocal, feedback-generated reality.” Yup. That helps to explain why planning dominates strategy and technocrats are more prevalent than strategists in the modern world of business.
Not every reader was an enthusiast: “Strategy as a process is trivial… [it is] knowing what sequence of actions will result in the desired outcome. The reason why most strategic advice is crap is because its coming from someone who doesn’t actually know how to come up with those action sequences.” Not exactly sure what the prescription of this view was. But it was stated with enthusiasm!
Without further ado, the original article…
Chapter Six
I have become increasingly troubled by a phenomenon in strategy — enough that I have decided to try to do something about it. Strategy is becoming the lost art and I have launched a restoration project. And as part of that project, I am making my 6th Year II Playing to Win/Practitioner Insights (PTW/PI) piece on The Lost Art of Strategy. You can find all previous PTW/PI here.
A Bit of History
When considered in the context of the evolution of the practice of strategy, I have had an interesting career. I was a full-time strategy consultant for 17 years, then I served as a business school Dean (and professor of strategy) for 15 years (during which time I continued to advise on strategy on the side), then I transitioned from academic to full time strategy advisor/writer over the past 8 years.



Roger, one additional turn of the screw on why planning keeps winning.
Planning is *organizationally compatible* in a way that strategy never can be. It produces shared documents, aligns calendars, generates the feeling of progress, and never requires anyone to confront the possibility that the firm's theory of winning is wrong or nonexistent. Strategy demands the opposite: uncomfortable truths about competitive reality, genuine uncertainty held open rather than collapsed into false confidence, and consequential choices that create visible losers before they create system-level winners. Organizations are coordination machines, and coordination selects for agreement, predictability, and the suppression of disruptive ambiguity. Those are the exact conditions under which strategy suffocates.
This is also why the AI problem is worse than benchmarking on steroids. AI gives organizations an extraordinarily efficient way to scale the *appearance* of strategic thinking (the polished frameworks, the well-structured scenarios, the articulate slide decks) without any of the painful judgment underneath. If firms were already substituting planning theater for strategic judgment, they can now produce that theater at industrial scale and with greater plausibility.
Strategy is not a lost art because we forgot the techniques. It is a lost art because the institutions we built are allergic to the conditions it requires. Your restoration project matters because what has to be restored is not knowledge of frameworks but organizational tolerance for the discomfort that real strategy produces.
Hi Roger!
The Lost Art of Strategy is one of the most fascinating topics in the field of strategy. Thank you for writing about it! An entire book could be written on it alone with so many examples that are seen everyday.
I thoroughly enjoyed all of your insights, especially the sections on the history of strategy and what happened with the key players who shaped it. It was really great.
What concerns me most is humanity’s growing habit of rushing everything—eating fast, reading fast, watching videos at double speed, and now even thinking fast.
I’m not against speed when it makes sense, but not everything should be rushed.
This raises some important questions (please don't answer them for me!, I just wrote them to reflect about what is happening).
How can a business leader truly understand what’s happening across all business dimensions if they demand answers desperately and urgently right now?
How will their mind form accurate hypotheses about the situation?
What happens when decisions are made so quickly that the choices were flawed from the very beginning?
Will those hasty decisions end up wasting significant time, money, and resources?
My final reflection on this is:
Are we entering an era in which deep thinking and reflection themselves are becoming also another lost art?