5 Must-Live-By Rules From History’s Masterminds

If Shakespeare, Alexander Hamilton or Sophocles taught an MBA class today, what would they say on the subject of leadership?

Now we might know.

In my forthcoming book, The Greats on Leadership: Classic Wisdom for Modern Managers, I explore the best leadership ideas of the past 25 centuries, using timeless authors such as Plato, Churchill, Shakespeare, Austen, Hamilton and Lincoln as guides.

Here are five timeless pieces of leadership advice from a few of those masterminds:

1. Machiavelli: Make big changes stick.
“It should be considered that nothing is more difficult to handle, more doubtful of success, nor more dangerous to manage, than to put oneself at the head of introducing new orders.”

That statement sits at the heart of Niccolo Machiavelli’s The Prince, one the most infamous leadership books ever written. For several hundred years after its 1513 publication, it was regarded as a how-to book for tyrants, dripping with sinister advice. In recent decades, however, it has been defended as a steadfastly practical examination of what does and doesn’t work for a leader who wants to make big changes.

Machiavelli knew cultivating change is one thing, while sustaining it another. He tells us, “Better to be feared than loved,” but when it comes to making change stick, this tough leader advises us to pay attention to the soft stuff: how people feel about the changes in question. Force may work in the short term, but in the long run, an effective leader knows it’s a matter of winning over hearts and minds. “For a prince it is necessary to have the people friendly,” says Machiavelli, “otherwise he has no remedy in adversity.”

2. Shakespeare: Stay in the learning zone.
Shakespeare’s Henry V, known for his inspiring speeches, is also the most self-reflective leader. But he never falls prey to analysis paralysis. In a crisis he moves forward, listening and course-correcting as he goes, transforming hatred and violence into lessons for a better future. He brings the same spirit of learning to his team members.

On the eve of his make-or-break battle with the French at Agincourt (Act IV, Scene i), a disguised King Henry roams through the army camps to discover the soldiers’ mood and what they think of him. The overheard conversations, not all of which are flattering, lead him to consider what it means to be a king. His musings reveal a leader in the learning zone—where our mistakes, my mistakes and their mistakes are pondered as one interconnected whole.

Later, right before the battle, he motivates his vastly outnumbered troops with a speech that, far from inciting fear or anger, appeals to their sense of pride and unity: This day’s anniversary “shall ne’er go by,” he says, “but we in it shall be remembered—We few, we happy few, we band of brothers.”

3. Jane Austen: Help people achieve their own greatness.
Jane Austen’s Emma features a heroine who loves to develop talent but takes the wrong approach. Emma Woodhouse’s excitement about one of her mentoring projects is reminiscent of some present-day managers’ misplaced enthusiasm for talent development. Watch how the “handsome, clever and rich” Emma pictures herself coaching her protégé: “She would notice her; she would improve her… she would form her opinions and her manners. It would be an interesting and certainly a very kind undertaking.”

Emma’s coaching efforts are well meant, but here’s the problem: Instead of cultivating people’s strengths, she tries to fix their weaknesses. The results are terrible. Her mistake is the same as that of the manager who writes employee development plans citing “opportunities for improvement,” or the supervisor who conducts “coaching sessions” telling you exactly how to do your job (which usually means exactly how they do it).

Leaders, Austen suggests, should spend less time trying to mold their team in their own image and more time helping them become better, stronger versions of themselves.

4. Plato: Be fair; be flexible.
Plato’s The Republic (featuring his famous teacher, Socrates) explores the surprisingly complex idea of what is due to groups, individuals and even parts of us.

The central question of the dialogue is, “What is justice?” Up front, someone says justice means being truthful and paying one’s debts—following the rules, one might say. But Socrates rejects this definition, citing the example of someone who borrows weapons from a friend only to find later that the friend has gone violently insane and wants the weapons back. Do you hand them over? Of course not.

This seemingly trivial example is actually quite serious: Justice can’t mean following the letter of the law, because we can always think of special circumstances, often having to do with a person’s intent or character, which would call for a different approach. Rules and policies are well and good, but if we don’t show appropriate flexibility—giving people their due diligence based on their role and the circumstances—we’ll be seen as unjust. Conversely, leaders who know when to bend the rules can be exemplars of justice.

5. Mary Shelley: Face your monsters.
Imagine making a bold move: an investment in critical new software, or a bet on an innovative product. Soon after rollout, you realize all’s not well. The software isn’t working. The product is flopping. It’s a nightmare.

What do you do? Do you run from the “monster” you’ve created? Or step forward and see how you can help?

In Mary Shelley’s Frankenstein, a cowardly leader runs from his scary creation. In one scene from the book, Dr. Frankenstein and his creature meet in a lonely forest. Frankenstein thinks he’s a dead man, but all the monster wants is to be heard. “I ask you not to spare me,” he says, “Listen to me, and then… if you will, destroy the work of your hands.”

Leaders show courage when they face their adversaries, but they show greater courage when they face up to their responsibilities. Often, that means standing calmly in front of your “monster” and listening to what it has to say.

By Jocelyn Davis