13 of the Best Books on Strategy

Ah, strategy. With an SNL skit, President Bush coinings the term ‘Strategery‘. Strategy is the effective approach to a goal. Any goal.  The better you are at strategy, the shorter the distance required to accomplish a goal. Strategy is about flexibility, options–putting people on the “horns of dilemma” because you have more strategic options available to pursue. Having multiple options nearly guarantees accomplishing at least one of the aims.

Strategy, according to Porter:

“Do what everyone else is doing (but spend less money doing it), or do something no one else can do.”

That definition skips the foundation of strategy. A foundation starting with military history. Strategy started as a military practice that was later adopted by the business crowd. The foundation in understanding strategy starts with understanding the military aspect. The ideas in these three foundation texts shape the business application of strategy.

Foundation on Strategy

1. Strategy by B. H. Liddell Hart

Strategy is the art of distributing and applying means to fulfill a goal. It’s not movement, but how effective that movement is. The perfect strategy remains accomplishing the goal without any serious loss. Executing the perfect strategy happens using the indirect approach along the lines of both least expectation and least resistance. Flexibility allows you to pursue alternative objectives putting your opponents on the “horns of dilemma.”

Dislocation and exploitation are the underlying fundamentals of a sound strategy. Concentrating on tactics means we forget “the necessity of making the enemy do something wrong.” Use speed along with the indirect approach. As Hart explains using strategy means “the longest way around is the often the shortest way home.”

2. 33 Strategies of War & 48 Laws of Power by Robert Greene

In 33 Strategies of War, Robert Greene created a list of 33 fundamental approaches and how to use them in all types of situations. The whole goal of strategy remains having as many different options as possible to accomplish the same goal. It’s to be flexible in the approach. Greene gives page after page over 33 different chapters filled with strategies to use–defensive and offensive. It’s a strategic action guide to help win all types of wars. That’s including Susan’s petty office battles.

3. The March of Folly: From Troy to Vietnam by Barbara W. Tuchman

Married to Failure, each story illustrates rejecting reason. Rejecting counsel in each case this book gives examples in history where failure wasn’t fate, but directly from the action or inaction of leaders. Those same leaders had strong council against those actions, yet decided to continue.

“when the soul is opposed to knowledge, or opinion or reason which are her natural laws, I call folly.” — Plato

This is a book about Ego. It’s example after example where “desire disagrees with the judgment of reason” and leaders persist in a faulty strategy. A strategy that pursues failure until it causes the fall of Troy. The stories show the failure to recognize the error, cut loses and pursue a different strategy. It’s protective stupidity. Protected from questioning. Protected from data that suggests different opinions. Protected from historical examples. The cure for the march of folly remains wisdom, moral courage, and reason. Create a strategy, but don’t be married to failure after the strategy is marching towards folly.

4. On Grand Strategy by John Lewis Gaddis

Yale Professor Gaddis brings his strategy class in book form with On Grand Strategy. Gaddis uses slices of historical texts and figures to deliver insights on strategy. From Thucydides to Lincoln, the indirect way and the difference between Foxes and Hedgehogs shows how the best strategist maintain a laser focus on the goal while also maneuvering past obstacles.

On avoiding strategic blunders, Gaddis notes “common sense, in this sense, is like oxygen: the higher you go, the thinner it gets.” Strategy across all time and space is about adjusting means to ends and having the patience across time to accomplish those ends.

5. The Book of Five Rings by Miyamoto Musashi

Musashi deals with the principles of strategy. Mastering the approach. The principles of strategy work regardless of fighting for yourself like Musashi or leading an army of 10,000. The principles are the same. It’s about managing the void. By knowing all the strategic approaches, you can know what doesn’t exist.

Mastering strategy is then mastering as a carpenter masters his craft–practice. A carpenter masters his craft using a master plan, masters the tools, and masters his men to build each house. A carpenter also sharpens his own tools. Musashi reiterates the need to practice and study all techniques to truly learn and master strategy. A carpenter uses the ideal rhythm to build a house. It’s neither speed nor a slow approach. It’s always a deliberate pace.

Biographies as Strategic Manuals

6. Napoleon: A Life by Andrew Roberts

One of history’s greatest military strategist highlights Napoleon’s revolutions in military supply, tactics, and planning logistics of warfare. Napoleon’s fascination with classic wars and Roman history started an education that would become not just a military genius but like “his own hero Julius Caesar, he was one of the greatest soldier-statesmen of all times” as described by Roberts.

More on Napoleon’s strategic genius: Napoleon’s Glance: The Secret of Strategy by William Duggan, The 33 Strategies of War by Robert Greene covers Napoleon in several parts of the book.

7. Washington: A Life by Ron Chernow

Even while losing more battles than he won, Washington is an example of losing the battle to win the war. Washington proves his strategic genius more in knowing how to keep the revolution alive in his troops for 8 years.

Study Washington as a strategic genius to highlight the differences between ambition without an end goal in mind (Napoleon) and Washington himself who’s one aim remained setting up a new nation. That aim is again served off the battlefield to set up the office of the president.

8. Genghis Khan and the Making of the Modern World by Jack Weatherford

Genghis Khan conquered more than twice as much as any other man in history. Surprisingly without Ego. Khan refused to have anyone paint his picture. When he died there were no monuments built. No one knows where he’s buried. He believed the law of the Eternal Blue Sky ruled over rulers and commoners alike. He introduced a new system based entirely on merit, loyalty, and achievement.

Like Napoleon, and later Erwin Rommel, Genghis Khan exploited speed, adopted new technologies, and perfected siege warfare.

9. Hannibal by Patrick Hunt

Hannibal might be one of the top strategists of all time. Even more apparent is the impact Hannibal had on Rome’s military strategy as Scipio Africanus adopted most of Hannibal’s tactics and strategy. From humbling Rome, to influencing the policies Rome would adopt to later defeat him.

Not only does strategy shine throughout Hannibal’s campaigns but leadership lessons abound. Hannibal was right with his men in each maneuver. Never taking asking his men to take the risk he wasn’t willing to take. Humbly sleeping on the ground with nothing more than a blanket galvanized loyalty amount all ranks of his men. While other generals allowed themselves to take the comforts of war along the road, Hannibal’s focus remained building support among allies and fellow Carthaginians alike.

Modern Strategy

10. Strategy Paradox by Michael E. Raynor

It’s the business equivalent of B. H. Liddell Hart showing that businesses need to have options. Strategic flexibility. Committing to one strategy increases the likelihood you will be both massively successful and massively unsuccessful depending on an unpredictable future. Other companies not willing to commit end up in mediocrity.

“Extreme positions in strategic space create the highest levels of profitability but also create the highest levels of strategic risk and hence failure.”

Since companies can’t know the future, companies can’t know if they are fighting the last war. It’s impossible to know if you should learn from defeat, success or rewrite the rules entirely. Even in the face of unavoidable uncertainty, the future still requires a commitment. The solution, according to Raynor, set up multiple parallel options. This gives you the flexibility to choose the winners as the future unfolds. It goes back to Hart’s maxim of pursuing alternative objectives.

11. Billion Dollar Lessons by Paul B. Carroll,‎ Chunka Mui

As the saying goes, only fools learn from their own experience. Billion Dollar Lessons dives into the biggest failures in strategy, failures from synergies, financial engineering, roll-ups, staying the course, consolidations and other painful lessons. It provides a blueprint on creating a culture and process to avoid blind spots in shaping strategies.

Just being aware of bad strategies doesn’t prevent them from happening. The best cure to avoid bad strategies involves empowering a devil’s advocate and fixing the flaws the devil’s advocate identifies. Learn from history. Deciding how to decide before a new strategic vision is needed ensures the right process is used. It’s deciding how to identify the right strategy to support the right desired outcome.

12. Blue Ocean Strategy & Blue Ocean Shift by W. Chan Kim, Renée Mauborgne

blue ocean strategy

Red Ocean. Blue Ocean. The choice is yours. Like Morpheus offering Neo a choice: Red Pill or Blue Pill. The red ocean is bloody. It’s filled with benchmarking, fighting for a smaller and smaller portion of an already shrinking pie. It’s insanely competitive.

Or there’s the blue ocean. The blue ocean is redefining the competition and making them irrelevant. It’s growing the overall pie and winning big. It’s about creating entirely new markets free of competitors.

In 2001, China entered the World Trade Organization. Since then the world has experienced a glut of supply. The entire world has become a red ocean. We’re all swimming in bloody, strong currents. It’s hyper-competitive today. And it’s not going to get any less competitive. It will be more competitive going forward. Using the Blue Ocean Strategy framework, your company can move away from head-on competition.

13. Strategy Rules: Five Timeless Lessons from Bill Gates, Andy Grove, and Steve Jobs by David B. Yoffie  and Michael A. Cusumano

Gates, Grove, and Jobs operated in a new competitive environment. They were the first to identify and successfully compete from building platforms instead of individual products. Platforms take advantage of network effects, which in turn, create stronger and stronger platforms.

Today’s competitive landscape cope with platforms, network effects, and shifting tech trends across more industries than just the tech sector. At the peak of their leadership, the combined market cap of Microsoft, Intel, and Apple was $1.5 trillion. Strategy Rules looks across these three leaders to find commonalities and core strategies used. Uncovered during the study of Gates, Jobs and Grove are five timeless lessons all types of companies can use to compete.

Other Notable Books on Strategy

The Art of War by Sun Tzu, On War by Carl von Clausewitz, The History of the Peloponnesian War by Thucydides, The Art of Strategy by Avinash Dixit, Competitive Strategy and Competitive Advantage by Micheal Porter, Buck Up, Suck Up . . . and Come Back When You Foul Up: 12 Winning Secrets from the War Room by James Carville & Paul Begala, The Lords of Strategy by Walter Kiechel, Playing to Win: How Strategy Really Works by Alan G. Lafley and Roger Martin, HBR’s 10 Must Reads on Strategy.

Crafting a Strategic Vision

Read to hone your strategic mind. Step back to consider all options to craft a strategic vision. Choose the right tactics to support the strategy that’s most effective at accomplishing the overall goal. Finally, study strategic failure to uncover the lessons of history.


This is part of a Real World MBA curriculum. Other parts of the curriculum include Management, Decision Making, Startups, Execution, Career Success, Finance, Dealing with People, Communicating, Ethics, Biographies and Marketing.