Seven Leadership Secrets from Shakespeare

A Five Minute Read

illiam Shakespeare – who would have turned 453 peopleon Sunday, if he hadn’t died 401 years ago Sunday – wrote a bit about kings, warfare, diplomacy, and the application of power. In other words, about what it is to be a leader. Specifically, a bad leader.

Bad behavior rules the canon. Being a humble, virtuous man did not make for great drama four centuries ago any more than it does now. (No one watches House of Cards, Scandal, or Billions for inspiring messages of hope).

Some plays offer little for today’s world: Macbeth is a charismatic but weak man goaded into becoming king by his wife, who ultimately exerts all authority. That’s certainly a tale of little relevance today, as is Lear, a king who descends into madness after transferring power to his daughters.

Shakespeare’s kings serve as a helpful primer on what not to do.

Having the Title Does Not Make You the Leader

Richard II’s flaw – besides being a scheming, greedy tyrant – comes from his sense of “royal privilege”. He believed that, as king, he was God’s chosen ruler; as such, whatever he wanted, God wanted, so he should have.

Not all the water in the rough rude sea
Can wash the balm off from an anointed king;
The breath of worldly men cannot depose
The deputy elected by the Lord

How often do we see others assume the mantle of leadership – from first-time floor supervisors to presidents and CEOs – presume that, because they are The Boss, whatever they say goes? Even if it were true, what good can come from building resentment and disparaging the very people we are supposed to inspire? (Rhetorical question!)

These tales always become ones of comeuppance; in this, Henry Bolingbroke, rightfully angered by his (and his family’s) treatment at the hands of the king, brilliantly builds a coalition and overthrows Richard.

That Said, Don’t Be Afraid to Lead

Bolingbroke was a great leader. Inspired by his mistreatment, he deposes the king and launches the House of Lancaster. But something happened between the curtain dropping on Richard II and opening on Henry IV, Part One. A brilliant tactician in taking power, as King Henry IV, he is incapable of actually using his power.

He tries to govern via bureaucracy. He fights battles (literally) on many fronts, attempting to prove his legitimacy and hold onto power. His creative energy was spent getting the job, and then on keeping the job. At no point does he articulate a vision for England, beyond getting his stolen silver back. Luckily, in modern times, we don’t see people leading campaigns for jobs, only to find out they don’t know what to do once there.

Uneasy lies the head that wears the crown

At some point, we all feel a sense of “imposter syndrome”. Surely, the thinking goes, there must be somebody better, or smarter, or more tactful, to be doing this than I. This is normal, and probably helps keep us grounded and humble, on our toes. Henry thought himself a fraud: Even after leading the movement against divine right, he started believing he had indeed usurped the throne, and lacked authenticity. This obsession hobbled his ability to lead.

Don’t Presume the Team Is Aligned

Skipping a generation brings us to Henry VI, a king so dysfunctional it took three plays to cover his failures. (Although the first of the three, “The Phantom Menace”, is just not very good.) Henry VI is nowhere near the leader (or man) his father was, and he starts to lose control of the French territories that Henry V had so masterfully won. (And because it’s a woman, of all things, besting him, he makes sure she is vilified as a witch and a whore).

Let me embrace thee, sour adversity;
For wise men say it is the wisest course.

His team fractures, and he is unable to hold them together. They quickly take sides and declare their allegiance:o underscore the complete lack of control, they wear red “I’m With York” or white “Lancaster Rocks!” roses to announce their loyalty (hence, “The Wars of the Roses”).

This lack of alignment leads to war and carnage. Today’s leaders aren’t faced with as much swordplay, but failure to engage the organization during troubling times – such as the loss of a territory – only begins to sow insubordination. (Even today, there are American Airlines pilots who still wear their “Cactus Finger” lapel pin protesting the 2005 America West merger with USAirways.)

Don’t Forget to Be Human

Shakespeare glosses over the Edwards – IV, who had a brief tenure in the middle of Henry VI’s reign, and later succeeded him; and V, who never made the highly-regarded/mostly meaningless 100-day mark – but goes all in with Richard III, as conniving and venal a character as ever staged.

Bacon said he was “a good lawmaker” – in other words, a policy wonk – but no one has ever had anything else nice to say. Afflicted with minor scoliosis (that “a good tailor” could have hidden, according to the Daily Mail), Shakespeare created the popular image of a monster – a “poisonous toad” with a twisted head, mismatched legs, a horrible lurch and a limp arm – that remains to this day.

So what was really wrong with the guy? Besides the fact that he sentenced his brother, the heir to the throne, to the Tower of London? And then dispatched assassins? And that he seduced the widow of Henry VI’s son, whom he had killed, putting the moves on her in front of the slain body of her father? Who just so happened to be Richard’s mentor? And he himself did the slaying?

He adopts a public persona of being a humble servant, lacking in pretentiousness and overflowing with piety, then executes his main detractor and spreads illegitimacy rumors about his competition. (We can all be thankful modern-day campaigns don’t behave this way).

Richard so wanted power that he did anything and everything to get it. Like Bolingbroke, he had no plans for what to do once in power. He did not want to lead, but to command. He wanted people to bow before him, and he found a way to make that happen. His violent and reprehensible path to the throne left little support or affiliation, and he realizes how alone he is whilst preparing for (what became) his final battle. Hell, even his horse famously left him.

Don’t Be Paranoid

Richard III – like another Richard, years later – saw enemies everywhere. If you look for adversaries, you will find them. Even if they weren’t foes to begin with, presuming that others are out to get you – or your job – leads to the leadership behaviors (secrecy, duplicity) that fuel rebellious fire.

If You Don’t Want the Job, Don’t Take the Job

Henry VI was regarded as a decent, honest guy – but had no desire to be king. Whether he was fundamentally unfit, or just had no interest in the job, he didn’t do it well. Many people take on roles because they feel it’s “what’s next”; even if it’s a necessary stepping stone, a lack of desire is easily read and leads to a lack of engagement. Henry IV didn’t want the job, either – he just didn’t want Richard II to have it.

Don’t Ignore Succession Planning

Shakespeare’s eight history plays treat Leadership as a family business – which was largely true for the Houses of Plantagenet, Lancaster, and York. In fact, Lancaster sets the prototype for the rise and fall of a family business – Henry IV builds the foundation, his irresponsible son rises to the challenge and flourishes in every respect, and the third generation lets it go to hell.


All is not winters of discontent in Shakespeare’s plays; in fact, for Henry V, almost all is well. From his proto-Ted Talk on the eve of Agincourt to his ability to build alliances, he was – and remains – a highlight of Western history. But St. Crispin’s Day – October 25th – is a more appropriate time to review his success.