The Five Books That Taught Me Most About Leadership

Only one of them is actually a book on leadership

Graeme Keith
10 min readMar 8, 2021


Photo by j zamora on Unsplash

The five books that taught me most about leadership are

  1. On Grand Strategy by John Lewis Gaddis
  2. War and Peace by Leo Tolstoy
  3. The Open Society and its Enemies by Karl Popper
  4. Talleyrand by Duff Cooper
  5. Middlemarch by George Eliot

By leadership, I mean the act of forging and articulating a vision and then engaging and motivating individuals in its execution. A critical component of this process is how the vision evolves, perhaps an expansion in scope or an intensification of its message, but most importantly, how the vision adapts when it runs into the unpredictable brute reality of the world.

I do not restrict leadership to management; this is not necessarily a list for CEOs and other hierarchical heads; this is as much about intellectual and moral leadership as managing your subordinates.

There are many ways books can teach us about leadership. By example is the simplest, which is why biographies can be such a rich source (though not, typically, authorized or autobiographies, which tend to be post-rationalized journey-to-success narratives rather than authentic accounts of personal struggle).

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Because the conception, articulation and evolution of vision is so essential a part of leadership, books that themselves articulate or embody visions are immensely rich resources, as are books that describe how vision evolves through discourse with society and the world.

The execution of a vision through leadership entails the motivation and engagement of individuals, so books that develop our human sympathy and our ability to connect and understand others are equally indispensable.

This article is not so much about these particular five books as about how we can learn about leadership from reading books like these: novels, political and philosophical works, biography, history and, now and again, books on leadership.

On Grand Strategy by John Lewis Gaddis

On Grand Strategy. John Lewis Gaddis. 2018. Penguin

In On Grand Strategy, Gaddis articulates his own vision of grand strategy as “the alignment of potentially unlimited aspirations with necessarily limited capabilities” and how that alignment is “necessary across time, space and scale” He describes how strategy is conceived and nurtured in the “relationships between the general and the particular — between universal and local knowledge” and how the “practice of [strategic] principles must precede their derivation”.

He achieves this through a breathtaking breadth of example. Part of his message is the universality of his vision for all kinds of leadership: military and political to sure, but also moral, intellectual and artistic. So he weaves a dense tapestry of narrative, drawing together military strategists (Xerxes, Pericles, Napolean and Kutuzov, Clausewitz), political strategists (Augustus, Machiavelli, Philip of Spain & Elizabeth I, Lincoln), moralists, artists and intellectuals (St. Augustine, Tolstoy, Isaiah Berlin). He shows how they create their visions and how they’re guided by them; and in doing so creates his own vision, by which he is guided. He…

“…seek[s] ‘knowledge of the past as an aid to the understanding of the future, which in the course of human things must resemble if it does not reflect it.’ [Thucydides] For without some sense of the past the future can be only loneliness: amnesia is a solitary affliction. But to know the past only in static terms — as moments frozen in time and space — would be almost as disabling, because we’re the progeny of progressions across time and space that shift from small scales to big ones and back again. We know these through narratives, whether historical or fictional or a combination of both. Thucydides and Tolstoy are, therefore, closer than you might think, and we’re fortunate to be able to attend their seminars whenever we like.”

War and Peace by Leo Tolstoy

War and Peace. Leo Tolstoy. 1865. Penguin

Tolstoy is the warp through which Gaddis weaves his great tapestry on grand strategy, because Tolstoy, like Gaddis, simultaneously creates and is guided by his own epic poetic vision. Tolstoy is both an exemplar and a preacher of strategic principle.

Tolstoy most obviously preaches his vision of leadership in the contrast he draws between Napoleon and the commander in chief of the Russian forces during Napoleon’s campaign, General Kutuzov. In Gaddis’ words “Kutuzov leads from a lower altitude than Napoleon: that keeps his head out of his own clouds”.

Here’s Tolstoy, for example, describing Napoleon’s delusions of executive agency at the battle of Borodino:

“From the battlefield, adjutants he had sent out… …kept galloping up to Napoleon with reports of the progress of the action, but all these reports were false, both because it was impossible in the heat of battle to say what was happening at any given moment and because many of the adjutants did not go to the actual place of conflict but reported what they had heard from others; and also because while an adjutant was riding more than a mile to Napoleon circumstances changed and the news he brought was already becoming false.

The marshals and generals, who were nearer to the field of battle but, like Napoleon, did not take part in the actual fighting and only occasionally went within musket range, made their own arrangements without asking Napoleon and issued orders where and in what direction to fire and where cavalry should gallop and infantry should run. But even their orders, like Napoleon’s, were seldom carried out, and then but partially. For the most part things happened contrary to their orders.”

(This passage resembles nothing so much as the daily operation of a modern international corporation.) Contrast this with (the fictional) Prince Andrei’s reassuring reflections on General Kutuzov

“…he will hear everything, remember everything, and put everything in its place. He will not hinder anything useful nor allow anything harmful. He understands that there is something stronger and more important than his own will — the inevitable course of events, and he can see them and grasp their significance, and seeing that significance can refrain from meddling and renounce his personal wish directed to something else.”

Tolstoy’s explication is poetic, but Tolstoy’s Kutuzov embodies Gaddis’ vision of leadership.

The less obvious lessons of leadership in Tolstoy are essentially human. As another of Gaddis’ grand strategic heroes Isaiah Berlin explains, Tolstoy wrote War and Peace to unveil his vision of historical exigency, but Tolstoy was too scrupulous a chronicler and too subtle an observer of human nature to subordinate his characters and their responses to historical events to a prescribed vision. Here, for Berlin, lies Tolstoys greatness; this absolute authentic rendering of humanity is absorbed into his great historical vision, which is made all the greater for it.

For the student of human nature, War and Peace provides insight into the inner workings of our fellow man on a scale to match Tolstoy’s historical vision, from the lowliest private to the greatest generals, from the salons and drinking dens of Moscow and Petersburg to the battlefield of Borodino.

The Open Society and its Enemies by Karl Popper

The Open Society and its Enemies. Karl Popper. 1945. Routledge

The Open Society, written as an intellectual bulwark against all forms of totalitarianism, right and left, has lost a little of its urgency since the collapse of communism. But as an impassioned articulation of Popper’s vision of a humane, reasonable, just and free society, it has lost none of its grandeur or persuasive power.

Like Tolstoy, Popper is both preacher and exemplar. His vision, descended directly from Socrates (via John Stuart Mill), is a civilization that is tolerant to all who are not intolerant, and (in opposition to Mill) that acts towards the minimization of suffering, as opposed to the maximization of happiness or well-being. The latter, he argues, is apt only to produce well-meaning dictatorships.

Writing in exile during the second world war, Popper’s vision stands in stark contrast to the totalitarian ideologies then ravaging the globe. Popper’s elucidation of enlightened leadership is cast largely by critique of the great intellectual leaders who — unwittingly and often with the best of intentions —have betrayed the civilization to which Popper aspires.

Take his assault on Plato’s Republic (a classical forerunner of many an international corporation), where he lambasts the Plato’s ideal of the philosopher king (read demagogue CEO) and extols the legacy of Socrates

“What a monument of human smallness is this idea of the philosopher king. What a contrast between it and the simplicity of humaneness of Socrates, who warned the statesman against the danger of being dazzled by his own power, excellence, and wisdom, and who tried to teach him what matters most — that we are all frail human beings.”

But he saves his most incandescent rhetorical heat that arch “thought-leader” Hegel

“Hegel… …was a flat-headed, insipid, nauseating, illiterate charlatan, who reached the pinnacle of audacity in scribbling together and dishing up the craziest mystifying nonsense. This nonsense has been noisily proclaimed as immortal wisdom by mercenary followers and readily accepted as such by all fools, who thus joined into as perfect a chorus of admiration as had ever been heard before.”

Talleyrand by Duff Cooper

Talleyrand. Duff Cooper. 1932. Vintage

Though no-one’s model of moral leadership, Duff Cooper makes a compelling case for Talleyrand’s claim to exemplary political leadership, steering both himself and his fatherland through surely the most tumultuous period of European history.

Talleyrand was an aristocratic bishop at the outbreak of the French Revolution. Through a combination of good luck and good timing, he managed to avoid the bloodshed of the reign of terror, sent to to England then exiled to the United States. Returning to France after the fall of Robespierre, he served as Foreign Minister to the Directory, but later allied himself to Napoleon, whom he subsequently served for following decade. Eventually disillusioned by Napoleon’s foreign policies, Talleyrand distanced himself from the Emperor and began to form alliances with others of Europe’s great powers. These machinations together with his extraordinary diplomatic skill made Talleyrand indispensable to the restored Bourbon dynasty. His extraordinary career had a fitting coda in his role in the July revolution, and the succession of yet another dynasty of French Royalty.

Such an uncanny instinct for survival suggests cynical opportunism and low cunning rather than masterful strategic statecraft and Talleyrand is an unlikely candidate for exemplar of unwavering vision. Such is the genius of Duff Cooper’s exegesis (and obvious, profound, respect) that Talleyrand is persuasively portrayed as not only faithful to every regime he served, but faithful to a clear unwavering vision for European peace and unity.

Talleyrand thus serves us as an extreme example of how a vision can be forged despite the backdrop of the most tumultuous chaos and, literally, terror; and how that vision can evolve and guide action despite the most astonishing reversals of political fortune.

“Talleyrand… …never found his defender in France. Yet it is not for the French to decry him, for every change of allegiance that he made was made by France. Not without reason did he claim that he never conspired except when the majority of his countrymen were involved in the conspiracy. Like France he responded to the ideals of 1789 and believed in the necessity of the Revolution; like France he abominated the Terror, made the best of the Directory, and welcomed Napoleon as the restorer of order and the harbinger of peace: like France he resented tyranny and grew tired of endless war and so reconciled himself to the return of the Bourbons…Constitutional monarchy, the maintenance of order and liberty at home, peace in Europe, and the alliance with England, to these principles he was never false — and he believed that they were of greater importance than the Kings and Emperors, Directors and Demagogues, Peoples and Parliaments that he served.”

Middlemarch by George Eliot

Middlemarch. George Eliot. 1871. Penguin

Where the obvious lessons on leadership in Tolstoy are explicit and the less obvious lesson found in his profound psychological authenticity, in George Eliot, the obvious lessons are exactly in the searing luminance of her analysis of human motives.

Nathan Sheppard in The Westminster Review, of which Eliot herself was an editor, wrote shortly after Eliot’s death,

“George Eliot is the greatest of the novelists in the delineation of feeling and the analysis of motives... She reaches clear in and touches the most secret and the most delicate spring of human action...”

Such is her intense affinity with her characters that like Tolstoy, Eliot can draw you into a deeply felt, vigorous dislike for some figure, only to melt that antipathy away in a single shaft of sympathetic insight. Unlike Tolstoy this is the aim of her craft, in her own words “uncovering human lots and seeing how they are woven and interwoven”.

This sympathy and understanding is essential to enlightened leadership and in this, all of Eliot’s novels and short stories serve as a rich source. But Middlemarch, A study of Provincial Life — the interwoven tales of an English Midland Town around 1830 — is a much richer seam of, less obvious, leadership inspiration.

This is because the three main protagonists of the novel all aspire, in each their way, to lead, and all fail: The doctor Lydgate, whose plan was to do good small work for Middlemarch and great work for the world; the scholar Casaubon whose unfinished book, The Key to all Mythologies remains to be condensed from “a formidable range of volumes” to “fit a little shelf”; and Dorothea “enamored of intensity and greatness”, who, “rash in embracing what seemed to her to have those aspects” marries Casaubon.

They do not fail in spectacular ways, nor are their failures post-rationalized turning points in a journey-to-success narrative. They fail as real humans fail. They make poor, ill-informed choices. They stumble, they blunder. Their failures are unheroic, provincial.

Their failures are our failures, the failures of our fellow travellers and the people we aspire to lead. Eliot through “the habit of thinking herself imaginatively into the experience of others” (a habit she ascribes to one of her tiny handful of unfailing heroes, Daniel Deronda) teaches us the same. We learn from all the all too human errors of her characters, not only to avoid those same blundering choices, but also to respond compassionately and sympathetically when they inevitably befall us.

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Graeme Keith

Mathematical modelling for business and the business of mathematical modelling. See for a categorized list of all my articles on medium.