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Where Caesar Went Wrong: Anatomy of a Boardroom Coup

4/22/2016 David G. Pumphrey
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Where Caesar Went Wrong

Shakespeare’s play Julius Caesar does what Machiavelli’s The Prince, the classic book on power and politics, could never do in words: it demonstrates in dramatic form what takes place at the highest levels of dysfunctional leadership.

Julius Caesar, as chairman, or executive chairman, as we would know it in 21st-century corporate terms, wants to rise above all governance restrictions, brushing aside regulatory regimes in pursuit of power. He is intelligent, victorious, and popular but becomes blinded by hubris. There is a coup, and he loses his job and his life.

It is up to a less able and, in the end, not-so-successful chief executive officer, Marcus Brutus, to move against Caesar. Next up is chief operating officer Caius Cassius, who “project-manages” the execution brilliantly but is too impulsive to be a leader.

Other board members, Mark Antony and Octavius Caesar, are leaders-in-waiting, each brilliant and effective. But Antony is led astray by distractions such as wars overseas and his lust for Cleopatra. It is left to the patient Octavius to assume eventual control of the known world’s sole superpower.

The play provides lessons for us all in how to manage teams in times of transformation and change. For example, the rule of Rome by the triumvirate that followed Caesar’s assassination was an expedient strategy that did not work. Triumvirates rarely do. They are imbalanced, with two of the leaders able to gang up on the third, or each one potentially heading in his or her own direction. An exception in our day is Google, where an outsider was brought in to run the company with the two founders. That CEO, who successfully mentored the younger leaders, eventually became chairman, and the founders stepped up to assume leadership roles.

Nowhere is the true character of leaders more on display than in the refining furnace of disruptive change. They will be either shaped and strengthened by the experience, becoming stabilizing influencers, or destroyed by it, becoming indecisive loose cannons.

While the brightest and the best leaders are inevitably attracted to power—they want to make a difference, after all—they must be persuaded to put aside personal ambition for the intrinsically exciting goal of driving change.

Pride: The enemy of a united team

A company that has a culture of encouraging individual enterprise and a cooperative team dynamic will find that success is a natural consequence. The leader who can engage and align the team will truly add value and gain competitive advantage through accelerated performance.

The aim of a business is to gain market share by out-thinking its existing or potential competitors and organizing resources to secure and expand the market.

Certainly the Roman Empire had done just that under Julius Caesar. But pride is the enemy of unity, and a team once bonded in a common purpose will rapidly turn on itself if the leader starts to pursue an individual agenda.

The power struggles on Caesar’s team revolved around an aristocratic republicanism versus a democratic monarchy. Those struggles resulted in political and economic turmoil, leaders being killed, and wars fought. The voices of the people and the ruling classes were in conflict, which led to riots and deaths. In the end, a form of monarchical government was established by Julius Caesar’s political heir, adopted son, and grandnephew, Octavius Caesar, who became Emperor Augustus.

Shakespeare saw a similarity with what was happening in England during his time—social unrest, religious upheaval, overseas wars, rulers who used change for personal benefit, uncertainty about the royal succession, and an unstable ruling class.

How often do we see similar challenges in our corporations today? Differing opinions on governance, strategy, culture, markets, succession, and career progression lead to serious disruptions in the operations, profitability, and value of companies. When this is fueled by hostile factions with personal ambitions, corporations quickly lose their competitive advantage.

Shakespeare’s Julius Caesar embraces characters with differing leadership styles. In the cauldron of political turmoil, they demonstrate more frailties than strengths, though they have all had successful prior careers. We can learn much from these tragic heroes that is relevant to our corporate leaders today.

Julius Caesar

Chairman, or executive chairman

Of all the characters, Julius Caesar is the true tragic hero. At the start of the play, he has had a victory over his old rival, Pompey, and his hero’s deeds in winning wars have given him authority and majesty. He has brought peace and prosperity to Rome, and the name of Caesar is revered by all the people.

But success has gone to his head. Instead of putting the country’s (company’s) vision first, he becomes vain and disconnected from the people and his team. He is swayed by the opportunity to gain supreme power as a hereditary king. Perhaps he dreams of starting a dynasty—his lover and confidante, Cleopatra, could become Queen of Rome and their son, Ceasarion, next in line to the throne.

He has it all, and yet when his “executive team” begins to plot against him, he doesn’t see it coming. He has no idea there is a conspiracy forming. He is a leader who is no longer aligned with his leadership group; he is out of step, and he has lost their support in the most dangerous way.

In the following passage, one of the Roman senators has begged Caesar to have mercy on the senator’s banished brother. Caesar shows no flexibility. In fact, he is breathtakingly arrogant, likening himself to the fixed North Star.


I could be well moved, if I were as you:

If I could pray to move, prayers would move me.

But I am constant as the northern star,

Of whose true-fixed and resting quality

There is no fellow in the firmament.

The skies are painted with unnumbered sparks:

They are all fire, and every one doth shine;

But there’s but one in all doth hold his place.

So in the world: ’tis furnished well with men,

And men are flesh and blood, and apprehensive;

Yet in the number I do know but one

That unassailable holds on his rank,

Unshaked of motion. And that I am he . . .

Julius Caesar (Act 3, Scene 1)

Caesar’s arrogance and a susceptibility to flattery lead to his demise. Moments after delivering this speech, Caesar is assassinated by the very people he thought he controlled with his charisma.

Marcus Brutus

Chief executive officer and conspirator

Marcus Brutus is a conscientious, reflective, and considerate leader who has given his life’s work to the cause of Roman liberty—“the noblest Roman of them all,” as Antony says later in the play. No one can doubt Brutus’s pure motives.

Brutus is devoted to Caesar as his leader. He has great integrity and leads from the front. Unfortunately, he lacks Caesar’s charisma and appears solemn and humorless. But worse than that, he has a wavering quality and is prone to misjudgment. He is not a confident political or military leader.

He is famous for his logic, but his arguments are flawed. When asked by the conspirators to join them, Brutus hesitates. He is torn between his loyalty to Caesar and his loyalty to the state. In the following speech, Brutus effectively talks himself into joining the conspirators by recalling the principle of the preemptive strike.


It must be by his death: and for my part

I know no personal cause to spurn at him

But for the general. He would be crowned:

How that might change his nature, there’s the question.

It is the bright day that brings forth the adder,

And that craves wary walking. Crown him that,

And then I grant we put a sting in him

That at his will he may do danger with.

The abuse of greatness is when it disjoins

Remorse from power; and to speak truth of Caesar

I have not known when his affections swayed

More than his reason. But ’tis a common proof

That lowliness is young ambition’s ladder,

Whereto the climber upward turns his face;

But when he once attains the upmost round,

He then unto the ladder turns his back,

Looks in the clouds, scorning the base degrees

By which he did ascend. So Caesar may.

Then, lest he may, prevent. And since the quarrel

Will bear no colour for the thing he is,

Fashion it thus: that what he is, augmented,

Would run to these and these extremities.

And therefore think him as a serpent’s egg,

Which hatched, would as his kind grow mischievous,

And kill him in the shell.

Julius Caesar (Act 2, Scene 1)

The fatal flaws that destroy Brutus the CEO are all related to judgment. He could execute a plan, even while not understanding the “why” of it. He allows the conspirators to take advantage of his honor; he believes everything everybody tells him, and, in his idealism, he thinks he is doing the right thing for the good of Rome, and this, too, blinds him.

Caius Cassius

Chief operating officer and conspirator

Caius Cassius is a passionate, intense, and highly energized individual. He is a pragmatic organizer and a shrewd negotiator. He is the behind-the-scenes operations man. But he is also a compulsive plotter and malcontent.

Envious and resentful of Caesar, Cassius is the lead conspirator, but he needs the imprimatur of the trustworthy Brutus in order for the conspiracy to succeed. Cassius is a scornful type who is not afraid to play one person against another to achieve his ends. In the following speech, he tells Brutus a story about Caesar’s weakness in order to persuade Brutus to join the conspiracy. This speech shows Cassius seething with envy but also shows his great ability to weave a tale and draw his listener in with persuasive language.

Cassius persuades Brutus to join the conspiracy. His passion and language have a profound impact on the thoughtful Brutus. Note the different techniques he uses: humor, storytelling, flattery, an appeal to Brutus’s honor, and—perhaps most powerful of all—Cassius shows Brutus how he can take charge of his own destiny: “The fault, dear Brutus, is not in our stars / But in ourselves, that we are underlings.”

The leadership lesson here is sound in that top team executives sometimes fail to speak up (“we are underlings”), but the solution offered by Cassius is rotten to the core and demonstrates his lack of ethics. For Cassius, the end justifies the means.


I cannot tell what you and other men

Think of this life; but for my single self

I had as lief not be as live to be

In awe of such a thing as I myself.

I was born free as Caesar, so were you;

We both have fed as well, and we can both

Endure the winter’s cold as well as he.

For once, upon a raw and gusty day,

The troubled Tiber chafing with her shores,

Caesar said to me, ‘Dar’st thou, Cassius, now

Leap in with me into this angry flood

And swim to yonder point?’ Upon the word,

Accoutrèd as I was, I plungèd in

And bade him follow; so indeed he did.

The torrent roared, and we did buffet it

With lusty sinews, throwing it aside,

And stemming it with hearts of controversy.

But ere we could arrive the point proposed

Caesar cried, ‘Help me, Cassius, or I sink!’ . . .

[So I, upon my shoulder, from the waves

Did bear] the tired Caesar: and this man

Is now become a god, and Cassius is

A wretched creature, and must bend his body

If Caesar carelessly but nod on him.

He had a fever when he was in Spain,

And when the fit was on him I did mark

How he did shake. ’Tis true, this god did shake. . . .

Ay, and that tongue of his that bade the Romans

Mark him and write his speeches in their books,

‘Alas,’ it cried, ‘give me some drink, Titinius,’

As a sick girl. Ye gods, it doth amaze me

A man of such a feeble temper should

So get the start of the majestic world

And bear the palm alone. . . .

Why, man, he doth bestride the narrow world

Like a colossus, and we petty men

Walk under his huge legs and peep about

To find ourselves dishonourable graves.

Men at some time are masters of their fates.

The fault, dear Brutus, is not in our stars

But in ourselves, that we are underlings.

‘Brutus’ and ‘Caesar’: what should be in that ‘Caesar’?

Why should that name be sounded more than yours? . . .

Now, in the names of all the gods at once,

Upon what meat doth this our Caesar feed,

That he is grown so great?

Julius Caesar (Act 1, Scene 2)

Cassius is a leader who can get results but at a fatal cost to the organization. Toward the end of the play, Brutus and Cassius quarrel as Rome descends into civil war. Cassius believes that it’s fine to bend the rules and take a few bribes in order to get things done—the end justifies the means. But Brutus sticks to his principles. Cassius’s true nature is demonstrated at the Battle of Philippi, where his impulsiveness and impatience lead to his undoing. Wrongly believing that the battle is lost, he kills himself, so as not to fall into the hands of the enemy.

Mark Antony

Director and political heir to Caesar

Mark Antony is a complex character. He is the antagonist to Brutus and Cassius, but his motives are not pure. He is loyal to Caesar but is ambitious for his own ends.

Antony confronts the conspirators as a revenger on behalf of the people but also as a pragmatic politician sounding out what is in it for him. He is articulate, persuasive, menacing, and, above all, manipulative. He is a larger-than-life character who parties a lot and enjoys the arts, whereas his enemies are a more serious and politically minded group.

In his speech to the people after Caesar’s death, Antony positions himself as the obvious heir, who will give them the political and economic future they desire. He faces an initially hostile crowd, but through brilliant oratory, Antony quickly makes them question their assumptions about Caesar and therefore about the conspirators. Are they really “honorable”?

The lesson here is that leaders need to be aware of what motivates the individual members of their team. Are team members running their own agendas at the expense of the corporate goals?

Antony is an opportunist who ultimately defeats Brutus and Cassius and survives the Battle of Philippi. He later goes on to another major campaign in Egypt, where he takes Caesar’s former mistress, Cleopatra, as his lover.

Antony is a leader who is highly capable but who has no scruples. He exploits people around him to achieve, by fair means or foul, his own ends.


Friends, Romans, countrymen, lend me your ears:

I come to bury Caesar, not to praise him.

The evil that men do lives after them;

The good is oft interrèd with their bones.

So let it be with Caesar. The noble Brutus

Hath told you Caesar was ambitious:

If it were so, it was a grievous fault,

And grievously hath Caesar answered it.

Here, under leave of Brutus and the rest—

For Brutus is an honourable man;

So are they all, all honourable men—

Come I to speak in Caesar’s funeral.

He was my friend, faithful and just to me;

But Brutus says he was ambitious,

And Brutus is an honourable man.

He hath brought many captives home to Rome,

Whose ransoms did the general coffers fill.

Did this in Caesar seem ambitious?

When that the poor have cried, Caesar hath wept:

Ambition should be made of sterner stuff.

Yet Brutus says he was ambitious,

And Brutus is an honourable man.

You all did see that on the Lupercal

I thrice presented him a kingly crown,

Which he did thrice refuse. Was this ambition?

Yet Brutus says he was ambitious,

And sure he is an honourable man.

I speak not to disprove what Brutus spoke,

But here I am to speak what I do know.

You all did love him once, not without cause:

What cause withholds you then to mourn for him?

O judgment, thou art fled to brutish beasts

And men have lost their reason. Bear with me:

My heart is in the coffin there with Caesar,

And I must pause till it come back to me.

Julius Caesar (Act 3, Scene 2)

Antony, one of the non-executive directors, is ultimately unable to create positive and stable environments in which to resolve problems. He is a true example of a leader who runs his own agenda at the expense of the corporate goals.

Octavius Caesar

Director and Caesar’s grandnephew and political heir

Octavius Caesar is 18 years old when Julius Caesar is assassinated and 21 years old at the Battle of Philippi. He is one of the three political heirs to Caesar, together with Mark Antony and Marcus Lepidus. The three of them rule the Roman world after the fall of the Republic.

Octavius plays a secondary role to Antony in this play, but the final lines of the play come from Octavius, honoring Brutus’s death and declaring the battle over. The following two speeches are the last in the play. Note the difference in tone between Antony’s emotional appeal and Octavius’s neat pragmatism.

Octavius is the young aspirant for future honors and success. He rarely makes a political mistake, and, following Antony’s inevitable demise, he finally achieves his desire, ruling over Rome as the Emperor Augustus.

Like the best chief executives, Octavius, while clearly ambitious, has played the long game and thought through the ending (his ascent to the top job). He has sized up the situation and taken his team into his confidence. They are engaged and aligned behind a purpose.

Praising the former leader to retain the loyalty of his devoted followers is a time-honored practice, taken up by both Antony and Octavius.


This was the noblest Roman of them all:

All the conspirators save only he

Did that they did in envy of great Caesar;

He only, in a general honest thought

And common good to all, made one of them.

His life was gentle, and the elements

So mixed in him that Nature might stand up

And say to all the world, ‘This was a man!’


According to his virtue let us use him,

With all respect and rites of burial.

Within my tent his bones tonight shall lie,

Most like a soldier, ordered honourably.

So call the field to rest, and let’s away,

To part the glories of this happy day.

Julius Caesar (Act 5, Scene 5)

Octavius understands the key issues. He takes the bones of Brutus—all the real and imagined evils that died with him—and, in a marvelously theatrical gesture, buries the past, takes control, and shows his team the way forward.


Members of our Roman “boardroom team,” despite their many individual strengths, fail to operate as leaders in an effective and functioning team.

Today’s business world is characterized by transformation, change, and disruption, and the same dynamic applies now as then: order gives way to chaos whenever hubris is allowed to develop. The senators who brought down Caesar had ample warning of impending danger. Their mistake was a disorderly, short-term fix to a long-standing issue, which led to even more disorder. Octavius learned the lesson well. His patience and superior planning showed what true leadership is all about.

About the author: David Pumphrey is a partner emeritus of Heidrick & Struggles’ CEO & Board Practice and a life member of Bell Shakespeare, the Australian performing-arts company. The author would like to thank James Evans, associate director of Bell Shakespeare, for his contributions to this article.

This article was adapted from Where Caesar went wrong: Anatomy of a boardroom coup, one of two publications marking the 400th anniversary of Shakespeare’s death. For the full version, click the download link above.

For Shakespeare’s mind for the future: A modern-day tale, a commemorative collection of articles, click here.

David G. Pumphrey Partner Emeritus +61 2 82052000

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