If my book The Greats on Leadership has whetted your appetite for classic authors with insights for leaders, here are a few dozen more. They’re grouped under seven common leadership challenges. All are available on amazon.com or at your public library.
1. AVOIDING LEADERSHIP TRAPS
When leaders stumble, it’s often because they’ve decided that being right is more important than being effective. The following books and stories illustrate the many forms of this central trap and the difficulties of climbing out once you’ve fallen in.
- Aesop’s Fables. Apollonius of Tyana, a first-century philosopher, said of Aesop: “Like those who dine well off the plainest dishes, he made use of humble incidents to teach great truths.” Among the fabulist’s many enlightening tales for leaders are “Belling the Cat” (about wishful thinking) and “The Eagle and the Jackdaw” (about overreaching).
- Animal Farm (George Orwell). It can be read as a satire, a dystopian picture of the future, or a roman a clef about the birth of the Soviet Union. Students of leadership should read Orwell’s story with an eye to the saying of John Stuart Mill: “Bad men need nothing more to compass their ends, than that good men should look on and do nothing.”
- Dream of the Red Chamber, also called The Story of the Stone (Cao Xueqin). One of China’s four great classical novels, this is the story of the aristocratic Jia family—once prominent, now in decline. As the story opens, their remaining wealth and power depend largely on one daughter’s position as an Imperial Consort. Where did they go wrong?
- “Last of the Troubadours” (O. Henry). It is the early twentieth century in the Texas-Mexico borderlands, but in this short story the world still consists of barons, workers, and troubadours. When one of the barons faces a problem and one of the troubadours tries to solve it for him, we see the disastrous consequences of misdirected initiative.
- “Melian Dialogue” in Chapter XVII of History of the Peloponnesian War (Thucydides). What happens when a group of leaders misunderstands the nature of power and miscalculates the amount of power they possess? In the tragic aftermath of their wartime parley with the Athenian navy, the citizens of tiny Melos learn that hope is not a strategy.
- The Orestia (Aeschylus). This trilogy of plays tells of a series of vendettas within a family, sparked by a father’s sacrifice of his daughter and ending with a son’s murder of his mother. In each case, the killer believes revenge is required by the gods, but each act of revenge only succeeds in arousing a different god’s wrath.
- Othello (Shakespeare). Othello, a great general held at arm’s length by those he fights for, is brought down by a devious advisor who plays on his insecurities. Like Melville’s Billy Budd, the story shows how a leader’s fears—fueled by ego—can blind him to the distinction between truth and lies, saints and snakes.
2. THINKING AND ACTING STRATEGICALLY
People often imagine that “strategic” means “coldly objective.” These classics teach us that the most strategic leaders are in fact those who attend to, and wrestle with, the messy emotions of their allies and adversaries.
- The Art of War (Sun Tzu). Napoleon and Douglas MacArthur claimed to have drawn inspiration from this text by ancient Chinese general and philosopher Sun Tzu (“Master Sun”). It addresses not only military strategy but also such topics as diplomacy, public administration, maintaining energy, and exploiting enemies’ weaknesses.
- The Odyssey (Homer). Homer’s epic poem centers on Odysseus, hero of the Trojan War, and his ten-year postwar voyage home to Ithaca. His metis, or cunning intelligence, allows him and his men to escape myriad traps and dangers along the way; meanwhile Penelope, his wife, must use her own tactics to foil a pack of unwanted suitors.
- On War (Carl von Clausewitz). Prussian military theorist Clausewitz might have titled his masterwork On the Execution of Large-Scale Initiatives Involving Fallible Humans with Incomplete Information. His theories are the basis for such present-day aphorisms as “the fog of war” and “no battle plan survives contact with the enemy.”
- “The Purloined Letter” (Edgar Allen Poe). This classic tale of blind spots shows us how a thing can be both invisible and in plain sight. The key to discovering the well-hidden, says mastermind C. Auguste Dupin, is not to look harder in all the usual places, but rather to step back and look for that which seems out of place.
3. LEADING ACROSS BOUNDARIES
This challenge is about working with people outside your sandbox: people over whom you have no direct authority and who may see the world very differently from you. The books below offer helpful theory and examples.
- Abraham Lincoln (Godfrey Benson, Lord Charnwood). This 1917 book has a place among the best two or three Lincoln biographies. Charnwood, a British academic and masterful storyteller, focuses on how Lincoln balanced principle and prudence in order to collaborate with all kinds, twist a few arms, and achieve great things.
- The Arthashastra (Chanakya). Its political pragmatism, seen particularly in its seven strategies for dealing with neighboring powers, has caused this ancient Indian treatise on statecraft to be compared to Machiavelli’s The Prince. Its scope, however, is far broader, covering all the qualities and practices of the Rajarshi: the wise and virtuous king.
- The Golden Bough: A Study in Magic and Religion (James George Frazer). To read this classic work of anthropology is to gain an appreciation of the myths that underlie and unite disparate human cultures. The thinkers who acknowledge a debt to it range from Hemingway to H.P. Lovecraft, T.S. Eliot to Ezra Pound, and Freud to Joseph Campbell.
- “In a Grove” (Akutgawa Ryūnosuke). Akiro Kurasawa used this 1922 short story as the basis for his film Rashomon. When a samurai is found dead in a bamboo forest, three eye-witnesses present contradictory versions of what happened. The story and the film ask whether “the truth,” filtered as it must be through perspective, is ever accessible.
- Persuasion (Jane Austen). Anne Eliot, unmarried drudge for her lazy, obnoxious family, seems anything but influential as this book begins. As the story unfolds, however, her quiet, graceful competence develops into a force that moves events and draws admirers. She starts out too easily persuaded; in the end, she is the persuader.
4. COACHING AND DEVELOPING OTHERS
These works get at the heart of coaching, which has nothing to do with telling and everything to do with showing, questioning, and involving. We learn that the key to developing talent is to draw out what is there, rather than try to inject what is not.
- A Christmas Carol (Charles Dickens). The subject is “grasping old sinner” Ebenezer Scrooge and his conversion to wise, kindly benefactor to the poor of London. The lesson is that people can change for the better, but only if someone opens their eyes to who they once were, who they are now, and who they really want to be.
- Experience and Education (John Dewey). The twentieth century’s most famous proponent of interactive learning, John Dewey must roll in his grave every time a manager does a PowerPoint info-dump. In this short book, he criticizes “static” teaching methods and explains how to create experiences that foster real learning.
- Meno (Plato). Are leaders born or made? It all depends on whether virtue can be taught—the question posed in this famous dialogue. Among the many truths to be gleaned from Socrates’ conversation with young Meno, perhaps the most important is that learning is the process of awakening the knowledge that’s already within.
- Silas Marner (George Eliot). Like A Christmas Carol, this is the story of a miser and misanthrope transformed. The change in Silas Marner, however, is brought about not by all-knowing spirits but by a child whose trust reconnects him to his community, demonstrating that those who simply have faith in us are often our best teachers.
5. DRIVING CHANGE OR INNOVATION
Change initiatives invariably kick off with a great deal of fanfare. Just as invariably, enthusiasm wanes. The following classics provide insight into the sober side of change: what it feels like (for real) and how to make it happen (for real).
- “Hyperion” (John Keats). Change is never welcomed by everyone. This unfinished poem about the fall of the old gods, led by Saturn, and the rise of the new, led by Jupiter, conveys what it feels like to be on the losing side of a change and shows the various ways in which the defeated ones cope with a new order.
- Life of Caesar (Plutarch). Here are Julius Caesar’s triumphs on the battlefield, his takeover of the Senate, his ascension to supreme power, and, finally, his betrayal and murder. While there’s plenty here about military strategy, Plutarch places far greater emphasis on Caesar’s ability to win support—from foot-soldiers and kings alike.
- “Of Custom, and That We Should Not Easily Change a Law Received” (Montaigne). The famous essayist writes about the extraordinary force of habit in our lives. If you’re excited about a change or innovation, reading “Of Custom” will dampen your enthusiasm; failing to heed Montaigne’s advice, however, may land you in worse straits later on.
- Speech on Reconstruction (Abraham Lincoln). Lincoln was a masterful executor of change, engineering one of the most complex political transformations of modern times: the abolition of slavery in America. In this, his last speech, he reveals a deep awareness of the effort required to keep a nation moving up the long hill of Reconstruction.
6. MOTIVATING A TEAM
Motivation is a matter of understanding why people do things and then tapping into that why. These speeches, war stories, and essays show how leaders can unleash the energy of their team and direct it toward a goal—even one that requires great sacrifice.
- “Ain’t I a Woman” (speech by Sojourner Truth). In this plea for women’s rights (delivered extemporaneously to an 1851 Women’s Convention and later transcribed in several versions), well-known abolitionist orator Truth connected with her audience in a way that was, according to one present, “magical.”
- “Battle of Thermopylae” in Histories, Book VII (Herodotus). A doomed rearguard of 300 Spartan soldiers held the pass at Thermopylae against the Persians, a hundred times their number. Ever since, this famous battle has been used as an example of how a small but free people defending their native soil can outfight a horde of coerced invaders.
- First Inaugural Address of Franklin D. Roosevelt. With the nation in the grip of the Depression, the thirty-second President of the United States began his inaugural address by stating, “The only thing we have to fear is fear itself.” Without denying the time’s dark realities, he urged that problems be faced in the “warm courage of national unity.”
- “I Have a Dream” (speech by Martin Luther King, Jr). Toward the end of the speech, King departed from his prepared remarks in response to Mahalia Jackson’s cry, “Tell them about the dream, Martin!” The next day, an article in the Los Angeles Times said King’s “matchless eloquence” had inspired the “conscience of America.”
- Talks to Teachers on Psychology and to Students on Some of Life’s Ideals (William James). James, the father of modern psychology, adopts an accessible style in this collection of lectures on the human mind and our motivations. Start with “The Laws of Habit,” “The Will,” and “On a Certain Blindness in Human Beings.”
7. BUILDING PRESENCE AND CONFIDENCE
From these classics we learn, first, that loud is not the same as powerful; second, that position and wealth are not substitutes for character; and third, that even the dispossessed can find the strength to be leaders.
- The Jeeves canon (P.G. Wodehouse). Rich and idle Bertie Wooster can’t seem to stay out of the soup. Fortunately his valet, Jeeves, is equal to every predicament flung his way. The quintessential servant leader, Jeeves could foil a hostile takeover while picking out your clothes for the day. Aspiring mainsprings have no better role model.
- Meditations (Marcus Aurelius). His empire beset with famines, plagues, and crumbling frontiers, this Roman emperor turned to Stoic philosophy. He wrote the Meditations for his own improvement; its theme is captured in one of his precepts: “If you are pained by any external thing, it is not this that disturbs you, but your judgment about it.”
- Their Eyes Were Watching God (Zora Neale Hurston). In this seminal work of both African-American and women’s literature, Janie Crawford narrates her life story. Married as a teenager, she escapes one husband, outlives another, and kills a third. As she grows, she finds her voice, learning first to speak out; later, to be silent when she chooses.
- True Grit (Charles Portis). “People do not give it credence that a fourteen-year-old girl could leave home and go off in the wintertime to avenge her father’s blood,” says Mattie Ross, the heroine of this Old West adventure. She teams up with a mean drunk named Rooster Cogburn, and together they show that leaders come in unexpected forms.