The final thing I’ll say about strategy is that the military metaphors break down pretty quickly in modern software contexts.
You’re not trying to “crush” or “defeat” an adversary, but use strategy to compel customer behavior in ways that helps them achieve their unmet needs in ways that also contribute value to your organization.
There’s no military strategy that can help you do that…
Yes, business strategy is mostly about competition to be chosen or favored, not at crushing an opponent. And, businesses compete every day, militaries only sometimes. Still, the idea of seeking an advantage pervades both.
Rumelt liked PTW - he mentions it as a positive example in some of his interviews. Martin isn’t a gracious in his book review of Good Strategy / Bad Strategy.
I think the difference is that Rumelt is a career academic, and Martin played the role of both the academic as well as the practitioner, and continues to coach CEOs to this day.
It has been edited to become a successful business book. The most important part is hidden at the end of the book - the actual strategy process - and it doesn’t really outline business strategy design well, as the examples are about product strategy. The where to play / how to win cascade’s real-life value in combination with starting the process with goals, is quite likely to lead to logical shortcuts and bad strategy.
Hi Joachim – If I understand correctly, you find the breaking down of the five boxes across the first chapters of “Playing to Win” less helpful than the later “Think Through Strategy” and “Shorten Your Odds” chapters? If that’s so, I’d like to hear more about your thoughts behind that.
Yes - compare this with his newer writing on his practitioner blog: https://rogermartin.medium.com/the-strategic-choice-structuring-process-5e116b12ae1f -- the trap of PTW is that it provides a very easy pathway down the wishful thinking strategy creation process. And in the end you even have a nice, one-slide PowerPoint that documents your impressionistic strategy. I don't believe any moment that this is what Martin wants people to do, but it is the most likely path they will follow. Organizations need help with strategic thinking and decision-making, PTW provides some of this as an afterthought - which is easily overlooked. I like Rumelt's bluntness better - by the way, he did a fair bit of consulting work too. Also have a look at Jeffrey Meiser's work: https://warontherocks.com/2024/05/bringing-a-method-to-the-strategy-madness/ (I built a causal strategy canvas based on his work).
Out of the 39 books listed here, only 1.5 are authored by women. That's one book and one co-authored book. Less than 4%. I really appreciate your work, Richard, but I'd like to challenge you here to expand the scope of what you consider foundational. Thanks.
Lot's of interesting stuff here but I would also have some fiction on this list: Wolf Hall as an exemplar of leadership; and Heart of Darkness as a warning about the risks for starters.
This is SO cool. I'm doing a strategic thinking ultralearning project involving reading 20 books on strategy, watching 6 courses, and creating 5 digital products. It's lit. You and anyone else in the comments can check it out here.
Strategy is so often framed around war and business, and so that’s where most of the material is found. Which of the above hit the hardest for you in a broader sense? Put another way, do any of the above make you feel better at strategy and better able to win in any endeavor—poker, monopoly, fantasy football—and make you see the basic idea of something in a completely new way? Which of these should fascinate and change someone who is not high up in business and not in the military etc.?
• What about _influence_ strategies? Soviet defector Yuri Bezmenov told us that only 15% of the KGB budget went for espionage, the rest was for trying to mold opinion in other countries. Jack Dziak’s book _Chekisty_ goes into how this was done
• Your readers will want to get the edition of Sloan’s General Motors book with the introduction by Peter Drucker, as his own professional, intellectual interactions with the Corporation let him place Sloan’s work in a larger context. And Sloan’s is a fine work. A chapter or two bog down in minutiae, but overall it’s interesting, even exciting in places. How does one simply invent the world’s largest, most successful industrial corporation from a place of debt and chaos? Basically Sloan and his contemporaries drafted a big sheet of paper about 1922, laid it all out. But the GM of 1922 didn’t look much like the grand design. Models, divisions were in disarray, so there was a lot of work to fit the template over the Corporation. And Sloan readily acknowledges failures along the way, the times they went off-script for reasons good or bad, but the master plan was always there to return to, rather than the irrational pronouncements of one all-powerful dude, as at Ford
Turns out I have a _lot_ of reading to do on strategy. For anyone who wants it, here's a little spreadsheet with all the above data + an Amazon search link (you'll have to pick which version you want for many of these books). https://docs.google.com/spreadsheets/d/1aIfqCfDadSfzraKnJQ_jzYTb0jc5CHX3lz2dyEMAOWU/edit?usp=sharing
Lad
For business strategy: + Rumelt's 'The Crux' as it matures his approach and Martin's Playing to Win (while older and flawed, still a valuable read).
The final thing I’ll say about strategy is that the military metaphors break down pretty quickly in modern software contexts.
You’re not trying to “crush” or “defeat” an adversary, but use strategy to compel customer behavior in ways that helps them achieve their unmet needs in ways that also contribute value to your organization.
There’s no military strategy that can help you do that…
Yes, business strategy is mostly about competition to be chosen or favored, not at crushing an opponent. And, businesses compete every day, militaries only sometimes. Still, the idea of seeking an advantage pervades both.
Hi Richard - Thanks so much for reviewing & for your wise response.
You have a way of capturing the essence of strategy through the most apt metaphors.
I'll go back and revisit military strategy through the lens of seeking an advantage.
If your readers here haven't yet done so, I highly recommend your interview with Lenny Rachitsky:
https://www.lennysnewsletter.com/p/good-strategy-bad-strategy-richard
I think the big thing is not to “make” strategy and give it to others to “execute” – it’s to coach them to create their own strategies
I believe what Rumelt said Not To Believe Anything with Winning and simple framework - like Martin’s book. I want to know his perspective.
Rumelt liked PTW - he mentions it as a positive example in some of his interviews. Martin isn’t a gracious in his book review of Good Strategy / Bad Strategy.
I think the difference is that Rumelt is a career academic, and Martin played the role of both the academic as well as the practitioner, and continues to coach CEOs to this day.
Thanks man for your clarification.
Really! The feud is hard to follow. :)
A very polite, asynchronous, and one-sided feud. ;)
What are the biggest flaws you see with “Playing to Win,” Joachim?
It has been edited to become a successful business book. The most important part is hidden at the end of the book - the actual strategy process - and it doesn’t really outline business strategy design well, as the examples are about product strategy. The where to play / how to win cascade’s real-life value in combination with starting the process with goals, is quite likely to lead to logical shortcuts and bad strategy.
Hi Joachim – If I understand correctly, you find the breaking down of the five boxes across the first chapters of “Playing to Win” less helpful than the later “Think Through Strategy” and “Shorten Your Odds” chapters? If that’s so, I’d like to hear more about your thoughts behind that.
Yes - compare this with his newer writing on his practitioner blog: https://rogermartin.medium.com/the-strategic-choice-structuring-process-5e116b12ae1f -- the trap of PTW is that it provides a very easy pathway down the wishful thinking strategy creation process. And in the end you even have a nice, one-slide PowerPoint that documents your impressionistic strategy. I don't believe any moment that this is what Martin wants people to do, but it is the most likely path they will follow. Organizations need help with strategic thinking and decision-making, PTW provides some of this as an afterthought - which is easily overlooked. I like Rumelt's bluntness better - by the way, he did a fair bit of consulting work too. Also have a look at Jeffrey Meiser's work: https://warontherocks.com/2024/05/bringing-a-method-to-the-strategy-madness/ (I built a causal strategy canvas based on his work).
Can you point me to which chapter in PTW? Or the microeconomics part? Thanks
But not as a substitute for strategy - as a way to bring it to life once you have it
My work leading software teams means I need to use different industry-standard ways to set goals – OKRs and KPIs can be helpful tools
I think you have to immerse yourself in all of them and pick & choose the pieces that resonate with your approach
And yes, there’s no one right way to do strategy
Wait what? Prof. Rumelt on Substack? Instant subscribe.
Out of the 39 books listed here, only 1.5 are authored by women. That's one book and one co-authored book. Less than 4%. I really appreciate your work, Richard, but I'd like to challenge you here to expand the scope of what you consider foundational. Thanks.
Thanks for the wonderful list! A couple of titles I wasn’t aware of. One title I’d suggest: Edward Luttwak’s https://substack.com/@edwardnluttwak?r=xjk3&utm_medium=ios&utm_source=profile Strategy: The Logic of War and Peace
Agreed.
Lot's of interesting stuff here but I would also have some fiction on this list: Wolf Hall as an exemplar of leadership; and Heart of Darkness as a warning about the risks for starters.
https://thesilkroadnexus.substack.com/p/from-humanoids-to-ai-agents-how-autonomous
The Boyd book is full of fake stuff
This is SO cool. I'm doing a strategic thinking ultralearning project involving reading 20 books on strategy, watching 6 courses, and creating 5 digital products. It's lit. You and anyone else in the comments can check it out here.
Love the mention of Chanakya btw.
https://www.notion.so/introspective/Template-Strategic-Genius-Ultra-Learning-Project-8-Months-March-8th-November-8th-2025-1-1c4af94c5f8d80569977d33d557e13aa#1c4af94c5f8d816c8e42d0c6c0ddf45b
https://rogermoser.substack.com/
33 strategies of war ?
I’ve been looking for something like this!
Strategy is so often framed around war and business, and so that’s where most of the material is found. Which of the above hit the hardest for you in a broader sense? Put another way, do any of the above make you feel better at strategy and better able to win in any endeavor—poker, monopoly, fantasy football—and make you see the basic idea of something in a completely new way? Which of these should fascinate and change someone who is not high up in business and not in the military etc.?
Great list, thanks for it
• How do the “36 Stratagems” relate to Sun Tzu?
• What about _influence_ strategies? Soviet defector Yuri Bezmenov told us that only 15% of the KGB budget went for espionage, the rest was for trying to mold opinion in other countries. Jack Dziak’s book _Chekisty_ goes into how this was done
• Your readers will want to get the edition of Sloan’s General Motors book with the introduction by Peter Drucker, as his own professional, intellectual interactions with the Corporation let him place Sloan’s work in a larger context. And Sloan’s is a fine work. A chapter or two bog down in minutiae, but overall it’s interesting, even exciting in places. How does one simply invent the world’s largest, most successful industrial corporation from a place of debt and chaos? Basically Sloan and his contemporaries drafted a big sheet of paper about 1922, laid it all out. But the GM of 1922 didn’t look much like the grand design. Models, divisions were in disarray, so there was a lot of work to fit the template over the Corporation. And Sloan readily acknowledges failures along the way, the times they went off-script for reasons good or bad, but the master plan was always there to return to, rather than the irrational pronouncements of one all-powerful dude, as at Ford
More here:
https://americanbusinesshistory.org/the-greatest-businessman-in-american-history-alfred-p-sloan-jr/
Strategist’s bookshelf? Right here
https://substack.com/@tedgioia/note/c-115310548?utm_source=notes-share-action&r=qpok