Why every entrepreneur should read Shakespeare

Disclaimer — if you can’t make it to the end of this article

The “Bard of Avon” is incontestably one of the most iconic literature figures of all time. His early plays, mainly comedies and tragedies, were later regarded as some of the most genuine works ever produced in these genres. His works are portraying the complexities of human psychology which offer lessons of leadership, management, and communication principles to contemporary managers.

Some of Shakespeare’s plays, such as Henry V, Julius Caesar, Othello, King Lear, Macbeth, or Hamlet have often been considered valuable sources of consultation to corporate practitioners in terms of managerial counseling. Persuasion and motivational speaking, as represented by characters like Henry V or Julius Caesar, are considered to bring great contribution to the process of gaining the respect of employees or even handling competition.

Since the concept of business has extended its boundaries to a roaring global level, many corporations are now cross-cultural, leading to a symbiosis of different types of leadership and management principles and style, concluding in a multitude of multicultural shaped mentalities and personalities co-existing and collaborating for the sake of the greater profit.

King Lear and the fool — William Holmes Sullivan

Books such as “Power Plays”, written by John O. Whitney and Tina Packer, and “Bardisms: Shakespeare for All Occasions” are works presenting Shakespeare as a “management consultant” which can always offer guidance for executives regarding their careers in the contemporary sea of sharks that we name business. Shakespeare has been considered a genius for his works, filled with lessons, principles, and practices of management.

Although vastly regarded as an exceptional artist, it is rather intriguing to acknowledge the fact that Shakespeare was in his time known as a businessman who overcame his condition to enter a world of luxury.

His abilities to manage people, market his talent, network with those in power not only aided him in running The Globe Theatre in an admirable manner, but turned him into the witty masterpiece creator, still preaching loudly, hundreds of years after his death.

He also received lessons of leadership from his father, who was a businessman, too, consolidating his ability to deeply analyze the challenges and opportunities brought when engaging the world of business. For these reasons, Shakespeare stands today in front of us through his works of undoubted genius as a resource, waiting to be exploited by curious, assertive minds.

A portrait of a genuine leader throughout history

It is safe to say that Shakespeare’s plays are stories about leadership rather than romantic love (ask anyone who actually read his works). His stories relate the rise and fall of their protagonists which, if analyzed and pondered upon, have the potential to answer many contemporary dilemmas the businesspeople that we know are currently facing. For this reason, many corporate leaders have found inspiration in the dramas of the Bard of Avon.

Many of the mistakes of Shakespeare’s most representative characters are similar to the ones happening in contemporary boardrooms and offices around the world. In Timon of Athens, for example, Lord Timon learns a precious but painful lesson about wealth, reputation, excess, and responsibilities. He spends excessively on luxurious banquets and on his image as a generous ruler, a habit which, against the warnings of his friends and councilors, leads to quantitative debt.

When he began to realize the outcome of his behavior, it was way too late to change, so Timon chose to isolate himself and avoid taking responsibility. His poor leadership choices and failure to anticipate the results of his own actions have turned his character into the epitome of the weak leader.

Similarly, traits such as charisma, diplomatic skills, and the sense of responsibility that helps the successful leaders in Shakespeare’s plays can be the same characteristics that contour the great contemporary leader. Othello, one of the most representative characters in Shakespeare’s works, is first presented to be a very dislikeable character and a rather ineffective leader.

However, when urged by Iago to hide from Brabantio’s rage, Othello refuses to run away and shows the courage to face the consequences of his actions, a trait of a leader who is willing to undertake responsibilities. Shakespeare later convinces us of Othello’s astonishing abilities to a greater extent at the point where he maturely and promptly receives threats of arrest for his audacious behavior, but still stands tall for his principles.

Warren Bennis, the distinguished professor of business at the University of Southern California, notes that “The Complete Works of Shakespeare” is the best read on Leadership and Change a young mind can ever find. He underlines the vision of heroic leadership that is presented and frankly states that nothing else than courage will get your people to march in the same direction as your ideas and visions go.

The importance of risks and sacrifices in leadership

“Shakespeare’s understanding of human behavior allows him to “wield the scalpel”, says Professor James Shapiro of Columbia University. He explains how Shakespeare has gained the needed intellectual ability and general managerial information to be capable of exploring leaders’ interaction with each other, their reaction to events such as threats, and the opportunities to build alliances and coalitions in order to gain power or influence in a certain field.

Most of the leaders we have set as examples were facing situations of great challenge, be it war or psychological turmoil. We cannot speak about a 21st-century war between nations, but we can undoubtedly discuss upon the races of corporations towards the top of the “food chain”, the contests between assertive, hungry entrepreneurs.

In Shakespeare’s Henry V, the English king needs to go against all odds on the eve of the Battle of Agincourt. His troops are outnumbered, discouraged and doubtful of a victory against the French. However, in a rousing speech to his top generals, he declares:

“‘Tis true that we are in great danger;

The greater therefore should our courage be, […]

We few, we happy few, we band of brothers;

For he to-day that sheds his blood with me

Shall be my brother; be he ne’er so vile”

Henry V, Act IV, Scene iii

Historians approximate the number of English soldiers to have been around 8000 men, while the French were represented by an army of nearly 30.000 soldiers. The risks that Henry V takes are unbelievably courageous and required an immense level of trust in his army.

The English achieve a smashing victory the following day and Henry’s military genius is widely recognized up to this day. This play and many others have served modern leaders such as Winston Churchill, standing as a strong metaphor for the triumph of effective leadership.

A person ready to take risks depicts a strong character, confident enough to understand that no matter the consequence, pacing forward is absolutely paramount in order to achieve greatness, for the road to success will always require one to step out of their comfort zone and embrace the unknown, and sometimes the odds that stand against them.

Risks not only involve a battlefield or somebody’s life, but it is represented by every occasion to achieve a goal or to overcome a situation which requires one to assume the possibility to lose a fight, a property, a life, or something way less. Coriolanus represents an example of a leader unwilling to exit his comfort zone and abandon his principles for the sake of adaptation to a different type of ruling than the one to which he was accustomed.

His undeniable strength and courage turned him into a great military asset, but given his conservative mindset, Coriolanus sees adaptation to any type of leadership different from his authoritarian, military-like style as an attack on his integrity and does not wish to risk it by no means. Had he adapted to a different type of leadership, Coriolanus might have become one of Shakespeare’s greatest military and political leaders, for his competence as a strategist is undeniable.

Leaders and the Force of their Discourse

A business executive can gain a notable advantage by learning to become a great story-teller so that he can always explain his ideas and visions simply and clearly to his colleagues and partners. Richard Olivier’s consultancy work on myth drama is based on the knowledge that every teacher, be it a parent, a professor or a coach understands the power of transforming a less into a clear, understandable story.

He says it is part of human nature and an authentic method of learning, it is used both for children and for well-educated adults, given the ease and the accessibility it offers, but also the effect it proves to have in making people of all ages understand even the most complicated and sophisticated concepts. Shakespeare’s leaders, often great story-tellers themselves, give us plenty of examples of the art of negotiation, persuasion, or motivational speaking.

Genuine leaders passionately believe that they can make a difference, reason for which, in many of his plays, Shakespeare presents The Leader as a powerful speaker who breathes life into their visions and sees exciting possibilities for the future, all this spoken into an utterly persuasive manner.

Shakespeare proved that leaders search for opportunities to change the status quo, to improve and embrace the novelty, the positive and innovative thinking, as well as convincing others, to be open-minded, and to accept challenges as they represent a ticket to long-term success. A leader that has the ability to effectively communicate his vision, also shows the wisdom required to properly manage the resource he possesses be it physical or human.

“Nothing is either good or bad, but thinking makes it so.”

Hamlet, Act II, Scene ii

By using a stern, yet temperate approach in front of the public even in situations that represent defeat, the speech induces a certain encouraging feeling that will undoubtedly contribute to a positive psychological impact of the situation upon the employees. A powerful speaker is thus to be followed and supported for his persuasion abilities.

Accomplishing the extraordinary in organizations is, undoubtedly, a major challenge, and a leader will always notice the quantity of effort that has been invested in getting the work done. They will, consequently, try their best to keep alive the hope and determination of their army, of soldiers or employees. We can fearlessly say that leaders do celebrate accomplishments and know that one of the best ways to assure stable, sustainable progress in an organization is to make people feel valued for their efforts.

“Once more unto the breach, dear friends, once more;

Or close the wall up with our English dead.

In peace there’s nothing so becomes a man

As modest stillness and humility;

But when the blast of war blows in our ears,

Then imitate the action of the tiger. . .

Henry V, Act 3 Scene I

“Shakespeare has a perfect ear,” says Ralph Allen Cohen, executive director at Shenandoah Shakespeare’s American Shakespeare Centre. “He caught the rhythms of speech; he was able to hear and imitate.” Shakespeare’s works are filled with motivational speeches and inspiring leadership know-how.

“All the world’s a stage”

One of his most quoted phrases, the phrase represents the beginning of a monologue from one of the Bard’s most famous plays, As You Like It. This speech compares the world to a stage and life to a play and makes a classification of seven stages of a man’s life. This passage has led to multiple philosophical discussions over time for Shakespeare’s ability to synthesize the patterns of a person’s life or even career into a passage not 30 lines long.

All the world’s a stage,

And all the men and women merely players;

They have their exits and their entrances,

And one man in his time plays many parts,”

(“As You Like It”, Act II, scene vii)

One of the interpretations of this passage contours the importance of effectively evaluating the strength of a leader’s greatest asset: his councilors, advisors, or even friends. Although, all individuals, separated, are “merely players”, their exits and entrances are absolutely essential for the development of a series of situations.

This series of happenings can influence the success of an emerging business, a revolution in an industrial field, a notable discovery, or a mere important agreement or contract. Let us take as an example the assassination of Julius Caesar and the conflict between Mark Anthony and Brutus.

This conflict could be considered rather instructive from the point of view of corporate minds, for its comparability to a board room conspiracy in terms of organizational reforms. A boardroom massacre resulted when the future governance of Rome came up as an issue on the agenda, concluding with Caesar being brutally removed.

Such crisis situations are created by Shakespeare to underline the importance of carefully managing the human resource a leader can operate, the large significance of listening, analyzing, and adjusting to the advice and opinion of the ones that represent a leader’s potential support.

A second interpretation places the leaders of today’s financial world on a tremendously large stage, the 21st-century world of business. The players are engaging in a series of duels for supremacy and creating competition and the relative balance between the fieriest contestants for power, wealth, and social status. These players are constructing the world we live in day by day, creating businesses, products, and services, mentalities, and principles.

The “stage” will always be craved by players of significance, people that can be a great asset to our society. Inspired by the strong Shakespearean characters such as Othello, Henry V, Julius Caesar, Mark Anthony, a young businessman may step into “the lion arena” ready for a fair fight, for he has gained knowledge of the strategies of leadership, the cunning works of the unjust, the threats and chances the partners and opponents have to offer.


Throughout this paper, we have analyzed the deeds, the speeches, and the ways of Shakespeare’s leaders, some driven by power, some by wealth, and some by justice. Nobody can precisely define the traits the genuine leader needs to possess in order to rightfully take this title, and yet we can all agree that weakness can never be one. Do we thus encourage authoritarian leadership?

William Shakespeare’s plays create the prototype of a rather unbalanced leader in terms of being earnest, courageous, imposing respect, and gaining control of armies or peoples and even regarding their methods of embracing the voices and advice they receive. In some cases, we proved that a “good” leader is not necessarily an efficient one.

As shown above, Timon of Athens surrounds himself with flamboyant banquets that create an image of generosity and never-ending wealth, but the collapse of his rule doesn’t fail to happen as a consequence of bad leadership, lack of courage, and sense of responsibility when facing the result of his deeds. Othello, as a contrast, proves to be brave enough to face the duke and the senate for his inappropriate actions, but ends up committing the horrifying murder of Desdemona, blinded by jealousy.

Characters like Julius Caesar are developing an authoritarian leadership, which proves to be effective in terms of justly ruling his empire, but defective when it comes to his collaboration with the senate and advisors.

Shakespeare’s work necessitates a careful study, but if understood and valued for what it represents, it can represent an immensely valuable resource for all leaders. The wisdom of the Bard lies within the pages of his masterpieces, waiting to be explored, deciphered, and exploited by businessmen and politicians, military strategists, lawyers, professors, leaders of all mentalities and cultures, authoritarian or not.

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