Strategy: A History And The Craft Of Strategic Judgement

Strategy: A History by Lawrence Freedman is useful because it shows strategy as the long-running craft of navigating power, uncertainty, influence, persuasion, coercion, and political constraint. For education, governance, AI capability, and organisational change, the lesson is that strategy is not just a plan. It is judgement under uncertainty.

Introducing Strategy

Currently, I’m listening to the audiobook of Strategy: A History by Lawrence Freedman.

As the title suggests it’s a book about the vast history of strategic thinking and how strategy came to influence many different aspects of our lives including business, politics, and, of course, warfare.

This is a big book but will appeal to you if you’re interested in political or military history, but also if you’ve tracked the rise of strategy in contemporary business-think since the 80s and 90s.

More broadly, though, this book will also appeal if you’re interested in the mechanics of influence, persuasion, power, and manipulation as seen playing out in current events, news media, and often over social media.

The author, Lawrence Freedman, is – among other honours and awards – a Commander of the Most Excellent Order of the British Empire. Which means he’s a legitimate “Sir” as in he’s been knighted by the Queen.

In Freedman’s case, his award was for a lifelong distinguished contribution in the defence and international security fields. He knows what he’s talking about and his book stands out as a significant work and brilliant historical overview of strategy and strategic thinkers.

What’s it about?

Freedman’s treatment of the content draws from classic content found in the Bible and The Iliad, or drawing from the greats like Sun Tzu and Machiavelli but also ranges from the military strategies of Baron Henri de Jomini and Carl von Clausewitz, to the revolutionary strategy of Marx’s class struggles, to Peter Drucker’s insights into corporate strategy, game theory in economics and many others besides.

At the heart of strategy, Freedman argues, are core issues relating to manipulation and control, and the unpredictability of our environment. All of these contribute to the challenge and drama of strategy and the need for strategic approaches that are fluid and flexible.

Why Strategy Still Matters For Education, AI, And Organisational Change

This matters beyond military history or political theory. Education systems, organisations, and leaders now operate in conditions shaped by AI disruption, assessment uncertainty, institutional pressure, workforce capability gaps, and public trust questions. In that environment, strategy is less about having a perfect plan and more about reading the terrain, understanding incentives, recognising power, and acting with disciplined judgement.

Reflecting on the ideas

Listening to Strategy has been an interesting experience for me as I’ve been reflecting on the similarities between this and another area of interest for me – that of craft and craftsmanship.

I’ve written about craftsmanship extensively both on my blog and on Twitter, and I was struck early on by how many parallels I could draw. For example, it’s certainly true that the strategist is not a craftsman in the same way that a blacksmith is a craftsman.

The weapons that the strategist forges are more abstract, but I was reminded of the work of Hephaestus – the god of fire and metalworking who made all of the weapons of Olympus.

The weapons that the strategist forges – the twin swords of deception and coercion – he must also learn to wield with impunity and ease. But the strategist is more than this too and has other tools in his tool box including strength, guile, force, practical intelligence, and intuition.

These tools are abstract, yet lend themselves to very practical and, often, physical application. As with the craftsman, there is no separation between hand and head. He is, in fact, like the traditional craftsman, a man both of words and action.

29 Stratitudes For Strategic Judgement

The following “Stratitudes” are not a summary of Freedman’s book. They are prompts for thinking about strategy as a craft: how people use power, deception, timing, communication, escalation, and adaptation when outcomes are uncertain.

Ant warfare 

Or Chimpanzee politics 

It’s not like you get to choose

Learning the craft of strategy
Means learning how to forge and wield
The twin swords of
Deception and Coercion
With impunity and with ease

The craft of strategy involves
Graduated escalation
From nuisance
To real pain
To absolute dread

Coercion now
Begets coercion later
Lesson in there

Deceit and cunning
Are tools of the underdog
As a man obedient to God
Just read your Bible

The strategist
Is both a man of words
And of action
A true barbarian

Strength
Guile
Force
Deception
All tools in the strategist’s toolbox

Strategy requires practical intelligence

Be more like Odysseus

Practical intelligence is strategic intelligence
But it’s also intuitive

Coalitions are a source of strength
And instability

“Social media is Sophist media” – Plato

Corrupt the enemy from within

Famine is more terrible than the sword

The capacity to deceive
And on a large scale

Annihilation or attrition

Exhausting your enemy is also a strategy

If you have the time for it

Strategy is inherently political

If you think your strategy is immune

To the influence of politics and politicking

Then you’re deluded

Convey menace
Provide assurance

Control the territory

Or

Control the communications

Long-range aerial bombardment
(This tweet is not about military air power)

Popular demoralisation
Demotivation
And panic
At scale
These are all strategies of war
Sound familiar?

Brain warfare
Aim for the head
Seek to confuse and disrupt

Psychological dislocation

Super man

or

Super Monkey

Choose

The strategist
Should think
In terms of
Paralysing
Not killing

Dislocation
Dissolution
Disruption
The three Ds of military strategy

Form a coalition
Or disrupt one

ο στρατηγικός άνθρωπος
The strategic man
Understands risk

Real life
Is more like Poker
And less like chess
To encourage uncertainty
This is the application of Game Theory
In the Craft of Strategy

Who Should Read Strategy?

If you’re a student of history or war you’ll probably enjoy reading or listening to Strategy by Lawrence Freedman.

I’m neither of these things but I was still drawn in and I think the reason was that I have enjoyed the work of Robert Greene who wrote 48 Laws of Power.

Greene’s books, while less about strategy in the sense that Freedman discusses, do deal with power and manipulation in very practical ways. If you like Greene, I think you’ll appreciate Strategy.

This is a long book whether you listen to it or read it. If you want to follow Freedman’s history of strategy in more detail, the book is available in audio, Kindle, and print formats.

• If you’re short on time, I would recommend getting the audible version of Strategy. This is what I did.
• If you don’t want to take up physical space on your already overcrowded bookshelf or bedside table, then get the Kindle version of Strategy.
• If you’re just a stickler for the old fashioned dead tree kind of consumption then you can get the print version of Strategy here.

Strategy is often treated as planning, but Freedman’s history shows something more difficult. Strategy is the craft of acting when power, uncertainty, incentives, and human behaviour cannot be fully controlled. That is why the book still matters for education, AI, governance, and organisational change. The question is rarely whether a plan exists. The harder question is whether people have the judgement to act well when the plan meets reality.

Related Strategic Pathways

• Consulting / AI, Capability & Education Change
• AI Capability & Judgement
• Educational Thought Leadership
• Education Is A Wicked Problem
• NZQA Micro-Credentials
• Power: A Smart Person’s Guide to Understanding It

FAQ: Strategy, Judgement, And Organisational Change

What is Strategy: A History about?

Strategy: A History is Lawrence Freedman’s broad history of strategic thinking across war, politics, business, economics, literature, and social life. It traces how people have tried to use power, persuasion, deception, timing, and judgement to shape uncertain outcomes.

Why is Strategy: A History useful for educators and leaders?

It is useful because education and organisational change are not purely technical problems. Leaders have to navigate competing incentives, institutional politics, uncertainty, trust, and limited information. Freedman’s history helps frame strategy as disciplined judgement, not just planning.

What does strategy mean beyond military history?

Beyond military history, strategy is the work of choosing how to act when the terrain is uncertain, people have different incentives, and outcomes cannot be fully controlled. It applies to education systems, governance, AI adoption, workforce capability, and organisational change.

How does strategy relate to power and influence?

Strategy always involves power and influence because it deals with how people try to shape behaviour, decisions, attention, resources, and commitments. Freedman’s book is useful because it shows that strategy is never separate from politics, persuasion, communication, and trust.

How does strategic judgement matter in education and AI change?

AI change creates uncertainty around assessment, capability, authorship, governance, and institutional trust. Strategic judgement helps organisations decide what to protect, what to redesign, what to test, and how to act before the whole environment becomes clear.