If you don’t devour history, you have no business calling yourself a strategist

From August 2025 -- Thoughts on history and strategy after a lousy musical in Toronto and a great podcast

How can you call yourself a business or technology strategist if you wouldn’t devour history? What other discipline offers such training data — gathered over millennia — on the idiosyncrasies of human endeavor? What else provides such insight into the dividing line between victory and catastrophe in human institutions? Literature sometimes helpful too.

History shapes the world we live in, creating the cultural, demographic, geographic, and economic factors that determines the success or failure of a strategy. I visited Toronto this weekend. Think of the history required to create a wealth, English speaking business nexus for an independent state – right on the northern shore of Lake Ontario!

An indifferent musical and a superb history podcast caused me to ponder the nature of strategic competence, the intersection of elite culture and strategic competence and how CIOs must use facts to shape corporate decision-making.

My son Matthew didn’t think much of “Natasha, Pierre and the Great Comet of 1812.” “It wasn’t about anything,” he observed. It’s fascinating to watch Matthew become more incisive each year, and he’s quite correct here. How does one start with one of the most important, infuriating novels of the 19th century and extract triviality? (Question for Update readers: who among you aspired to be Pierre and who Andrei? I wanted to be Rostov, but knew I never could be.)

CIOs need to assemble the facts that will drive better decision-making -- and understand them in the context of management dysfunction so to create impetus for better decision-making. What biases does the rest of the executive team have? What facts will help them transcend those biases and put aside internal maneuvering to focus on how to create massive value from technology?

Strategic competence as the father of victory

I read War and Peace on Wharton trip in 1995, plowing through it on bus rides through China. My classmates thought me odd. Except for John Ferrari, who told me he read War & Peace sitting in a tent in Saudi Arabia in 1991, waiting for Desert Storm to start. Turns out, he retired from the Army as a Major General. (https://www.aei.org/profile/john-g-ferrari/)

Tolstoy was a loon, but he asked two essential questions: why do people sacrifice for a cause — and what comes of that sacrifice? He dismissed the importance of commanders in favor of the Russian soul. What authored Edward Tufte’s devastating chart of Napoleon’s advance to and retreat from Moscow? Tolstoy offers millions of small decisions by millions of Russians – what Peter Turchin describes in “War and Peace and War: The Rise and Fall of Empires” as “asabiya” or the willingness to engage in collective sacrifice for the greater good.

At some level this is true. The willingness of troopers to fight rather than flee divides victory from defeat. But Tolstoy waves away strategic and organizational context. Frontiviki (i just couldn’t resist the anachronism) at Borodino and Smolensk fought to defend their homeland rather than prosecute some foreign adventure. The Russian Army may not have demonstrated the intellectual leadership in that era that it did in the early 1930s, but it roughly kept pace with post-1789 military innovation. Yes, court politics had a baleful influence on assignment of commands, but Kutozov, Bagration, Wittgenstein had all learned hard lessons in the near-constant combat that followed Bastille. Forget about the national soul: history suggests good troopers fight for competent leaders.

Take the Russo-Japanese War of 1905, which Sarah Paine described in her Dwarkesh podcast. (

) Same great Russian soul, but Japan handed the Tzar his backside. Yes, the war happened on Japan’s doorstep and thousands of miles from Moscow and Russia’s industrial base. That mattered, but only so much. The Russia Army was reasonably modern in 1812. By 1905 it was a laggard, in part because the officer corps valued social prestige over technical innovation. Even worse Tzar Nicholas elevated favorites based on personal loyalty rather than competence. Generals who, per Paine, could not read a map or identify a howitzer will not make good operational decisions. And will not command the confidence of their troops – elite incompetence makes asabiya impossible.

Paine points out that Japanese leadership demonstrated strategic competence and won. Russian leadership demonstrated strategic incompetence and lost. Which all but resolves to a tautology — winning states make decisions that create victory; losing states do not.

Elite culture as the midwife to strategic competence

Who can fail to marvel at Japan’s progression from the Meiji Restoration to Tsushima Straits to the deck of the USS Missouri in Tokyo? From near-total isolation to a seat at the top table of great powers and mastery of the East Asia littoral to calamity and occupation — all within one individual’s lifetime. How did this happen. Paine argues that hubris born of success replaced strategic discipline. And then she observed that after 1945, a second Meiji generate created the prosperous and democratic Japan that serves as an important pillar of the international order today.

The culture of elite decision-making is always and everywhere a puzzle. The British Empire reached flood tide after Versailles. Barely more than two decades later it was a strategic bankrupt. By 1918 the British Army had mastered combined arms and invented a new form of warfare. (https://www.nids.mod.go.jp/english/event/forum/pdf/2014/04.pdf?utm_source=chatgpt.com) Two decades later it stumbled through operations in Norway, France and North Africa. His Majesty’s government underwrote the invention of radio and the tank. Yet the Wehrmacht used them via Blitzkrieg to weeks across France in weeks.

And yet… bankruptcy was not catastrophe. In “How the War Was Won,” Philips Payson O’Brien demonstrated how Great Britain, no less than the United States, prevailed by dominating the “air-sea super-battlefield.” (The world needs a subway series. It also needs a debate between O’Brien and Richard Overy, who wrote “Why the Allies Won,” on the origins of victory.) Yes, the Spitfire was beautiful, but it also held its own with anything the Luftwaffe could put in the air (https://hushkit.net/2018/04/17/spitfire-versus-messerschmitt-bf-109-a-comparison-of-the-spitfire-and-the-bf-109-in-the-early-years-of-world-war-ii/). Think of the imagination and grasp of systems thinking demonstrated in the “Dowding System,” which combined the Spitfire and Radar into the world’s first integrated air defense system.

Did I mention how British boffins invented the discipline of operations research (yes I love history but operations research is pretty awesome too!) to win the Battle of the Atlantic, perhaps the most important one of the entire war? (Definitely read “A Game of Birds and Snakes” — the war gaming was wild — and “Engineers of Victory.”) Need I mention intelligence coups like that of the Double-Cross Committee and Operation Mincemeat. (Amy and Matthew took me to see the recent show. The musical numbers are wonderful. As for the book? I preferred Ewan Montagu’s telling of the story in “The Man Who Never Was,” which I read as a kid.) Perhaps Panzers within sight of Dover and Heinkels over Coventry cause elites to prioritize the essential over the peripheral?

Culturally, how did this all happen? Where did the gentlemanly amateurism Corelli Barnett described in “The Collapse of British Power” (which I think I read on a trip to Australian in 1995) curdle into anti-intellectualism and suspicion of, even contempt for, technical expertise? How did the same cultural matrix that elevated plodding, unimaginative leaders like Percival and Ritchie also produce innovative mavericks like Slim and Wingate?

Facts as a driver of elite culture

So what do CIOs do in the face of poor executive decision-making? If we believe (per BH Liddell Hart) that strategy is the linkage of ends and means, then three questions matter in the context of any strategy, even strategies related to how companies derive value from technology.

What ends matter to you? As Paine pointed out, the Japanese Empire had a much better grasp of its ends in 1905 than the Russia one. Port Arthur was existential to Japan and peripheral to the Tsars. Because Japan grasped its ends, it saw when it reach the culminating point of victory and quickly ended the war by requesting mediation from Teddy Roosevelt.

Where do you connect ends and means? Yes, I have to read “Victory to Defeat,” (about the British Army’s interbellum decline in operational art), but it may be more interesting than important. O’Brien is probably right that Allied (American no less than British) deficiencies on land battle paled in significance compared to their innovation and success at sea and in the air.

But most importantly: how do you create an institutional culture that demands rigorous strategic thinking about technology, especially from its senior leaders? How to you get CEOs, CMOs, CFOs and the who have never thought rigorously about technology and who may barely understand it? Especially in advance of calamity or near-calamity.

How do you expunge anti-intellectualism from a culture? How do you celebrate and reward technical innovation? How do you force managers to engage in hard trade-offs (that lie at the core strategy!) rather than waving them away? How do ensure you make decisions predicated on demands on the external environment rather than placating internal constituencies? How do you create space for people closest to the cold face to surface unpleasant realities? Here is Overy’s point — the Allies had better decision-making processes than the Axis. (Both “Ministers at War” by Jonathan Scheer and “The Washington War” by James Lacey also provide important color here. Also O’Brien’s biography of Admiral Leahy). Even Soviet decision making improved after the wars initial months. Yes Marshal Zhukov was a monster, and he lived by a moral code we lack the capacity to imagine. But spare a thought for the man who walked in Joseph Stalin’s office to deliver news the zhvod didn’t to hear.

I don’t have an answer, but I have a hypothesis. Back in 2001, I spent every other week in London for six months. American Airlines loved me more than mother.

After the very final meeting for the project. I realized that I had hours until I had to leave for LHR and that I had spent all my time in London in client conference rooms and hotel bars so I went for a walk. I stumbled on an ANZAC day commemoration and stood among (and I exaggerate here not a whit) a crowd of people sobbing in the street. Lest we forget.

I wanted to see Downing Street, but even before 9/11 it was blocked off, so I paid a few quid to tour the museum they made of Churchill’s war time bunker. It was touristy and tacky, but Churchill’s conference room was fascinating — it looked as it a operations review deck had exploded there. The walls were covered with, well, slides — tonnage launched versus tonnage sank per month, average calories consumed by age per person per day and the like? Who, I wondered, must have created these charts for Churchill? Someone like me?

Organizational change management (as opposed to change control) is epistemological. My old professor Burr Litchfield (Dispute the proposition that the world needs more history professors named after Aaron Burr — I dare you!) used to say “In political science, they have the theories Here in the history department we are the custodians of the facts.” Just like this faceless people who created charts for Churchill, astute CIOs must be custodians of the facts.

But not only custodians of the facts — CIOs must understand them in the context of potential management dysfunction so to n create impetus for better decision-making. What biases does the rest of the executive team have? What facts will help them transcend those biases and put aside internal maneuvering to focus on how to create massive value from technology. (I could reference the Boyd cycle here, but wont because it’s become such a cliche.)

And CIOs must be as Zhukov, willing to march into Stalin’s office with unpleasant news and choices. Fortunately, it’s been decades since a CEO dispatched a partner of the Firm to the basements of Lubyanka and even then it only happened a couple of times. (Interestingly, the All Russia Insurance Company built Lubyanka before the revolution as its headquarters.)

How do CIOs develop the organizational insight and create the required facts to help the executive team make better decisions

?