Shall I Compare Thee to a Leader? Shakespearean Insights into Modern Leadership

Between 1986 and 1997, as the editor of the Currency book series, I explored the concept of leadership as a catalyst for change in both business and society. During this time, I had the privilege of collaborating with remarkable CEOs such as Andy Grove of Intel, Dee Hock of Visa, Max De Pree of Herman Miller, Phil Knight of Nike, and Howard Schultz of Starbucks. My central question to each of them was consistent: What are the essential elements of great leadership, and why are truly great leaders so few and far between?

My exploration revealed a surprising truth: even these highly successful individuals, including the CEOs whose books I published, struggled to articulate the secrets of their success more effectively than an external observer. However, certain anecdotes, often shared off-the-record, hinted at a recurring theme at the heart of leadership – the significance of pretense, role-playing, and theatrical techniques. One story from Intel about Andy Grove particularly captured my attention. Grove insisted that his exceptionally intelligent but reserved managers attend a seminar known as “wolf school.” This training taught them how to confidently confront superiors and forcefully present their ideas. By projecting an unwavering belief in themselves, they could persuade Intel’s demanding managers of their proposals’ merit. Even if they lacked genuine confidence, they were instructed to act as if they possessed it. The underlying message was clear: embody power, and you will become powerful. Transform your hesitant voice into a commanding roar.

Intriguingly, many leaders I encountered seemed most effective when they were, paradoxically, least authentic. It was as though their leadership capacity was cultivated not through discovering their genuine selves, but rather through embodying a character. Roger Ailes, in a 1988 conversation, aptly described this phenomenon as the “theater of leadership.” I had recently published his book, You Are the Message, co-authored with Jon Kraushar, a guide to public speaking and media presence. Ailes, then an independent television producer and Republican campaign strategist instrumental in crafting Ronald Reagan’s memorable phrases like “It’s morning again in America,” believed that the more refined and deliberately constructed a public figure’s persona, the greater their mythic and influential power.

Concerns about such image crafting are understandable, especially coming from the individual who later founded Fox TV and championed highly partisan figures like Rush Limbaugh, Bill O’Reilly, Sean Hannity, and Alan Colmes—all masters of constructing larger-than-life public characters. Yet, irrespective of political perspectives, consider this aspect of Ailes’s insight: What if learning to consciously adopt a role is indeed a crucial element of leadership development? What if this role-playing becomes a form of inner cultivation—not merely a facade, but a method for internalizing beliefs and values, solidifying them as you consistently express them within your organization? Cognitive neuroscience reveals that repeated actions physically alter brain pathways. It’s conceivable that by performing the role of a leader, one can develop the courage, decisiveness, and judgment essential for actual leadership. Anyone familiar with theater recognizes the transformative power of a skilled director in turning a novice into a convincing king.

While wholeheartedly embracing a role can lead to pitfalls like overconfidence or arrogance, this doesn’t negate the value of theatrical arts in leadership development. It emphasizes the need for careful role selection. Spending time immersed in the experiences of kings, queens, and princes navigating the complexities of power, as depicted in Shakespeare’s plays, becomes invaluable.

Prince Hal’s Eloquence: A Leader Compared to a Budding Flower

The Royal Shakespeare Company (RSC) in England also recognizes the role of playacting in shaping leaders. As the RSC described in a playbill for a 2007 Henry IV performance: “Shakespeare and his actors could convincingly portray royal figures, speaking as kings and queens ought to speak. Did this suggest that leadership is a performance accessible to any talented individual, regardless of background?”

This realization led me to Stratford-upon-Avon, Shakespeare’s birthplace, to visit the RSC during their preparations for a season featuring Shakespeare’s history plays. It was a unique opportunity to study power and performance, observing how historical rulers grappled with critical decisions, responsibilities, and consequences. I sought to understand what leadership insights could be gleaned from watching a theater director and their team of voice coaches and dramaturges at work.

Historically, influential leaders, particularly in politics, have drawn inspiration from Shakespeare. His plays are part of the curriculum at prestigious British barrister academies, the Inns of Court. Queen Elizabeth I transcribed parts of Henry V before addressing her troops against the Spanish Armada. Thomas Jefferson visited Stratford, reportedly even kissing the ground. Abraham Lincoln frequently read Shakespeare aloud to companions. Even today, Henry V is studied by Pentagon personnel in the Legacy Project for leadership development.

At Stratford, I began my conversation with RSC Artistic Director Michael Boyd by asking which Shakespearean leader he would choose to follow. Over a lunch of unappetizing beets and stew, Boyd cited Prince Hal, the central figure in Henry V.

Boyd explained, “Shakespeare explored various leadership styles: leading from the front, charismatic leadership, leadership by force. But in Hal, he showed a leader adapting to each moment’s challenges. Hal initially rejects authority, preferring a life of enjoyment. Yet, he is gradually compelled to embrace responsibility.”

Prince Hal, heir to a usurper king, initially distances himself from his father’s tainted reign. Boyd notes, “He shields himself from his privileged birth, rejecting the elite but ultimately accepting his royal duty. He sacrifices his dearest life to become a useful king.”

As Henry V, he becomes a pragmatic and decisive leader. His controversial act of banishing Falstaff, his close friend and mentor, upon ascending the throne, highlights his difficult choices. Boyd argues, “This doesn’t dehumanize Henry V. He is aware of his flaws and mortality, possessing humility. He reconciles with his father and prepares to embody the role of king. A leader without ambivalence about power is unconvincing.”

Prince Hal’s linguistic skill is crucial to his leadership. He adapts his tone to connect with diverse audiences, each style conveying power. Alison Bomber, the RSC voice coach, explains, “He has varied registers. He can speak to soldiers in their language, to churchmen in theirs. He can project authority with resonant vowels, and in battle, use sharp, forceful sounds.” He can even convincingly impersonate a tavern server, yet deliver regal pronouncements in moments of crisis. Laurence Olivier’s portrayal of Henry V often centers on these powerful speeches.

When asked if he saw modern parallels to Hal, Boyd mentioned Nelson Mandela, “due to his transition from opposition to leadership, maintaining integrity.” He also saw Hal-like qualities in Gordon Brown, then UK Prime Minister, hoping he would retain his “common touch.”

However, Boyd acknowledges that Henry V, while eloquent like Mandela, is not a saint. His war with France was based on a dubious claim, fueled by anger. Yeats observed that Shakespeare likely didn’t admire Hal, finding him too calculating.

For leaders balancing competing priorities, Hal’s perseverance is relevant. Boyd advises, “Fully engage in every part of the journey, even the conflicting parts. Embrace paradox. Self-doubt is key to Shakespeare’s great leaders.” Like a budding flower pushing through the earth, a leader must emerge through challenges and doubts.

The Sacrifice of Richard II: A Leader Compared to a Setting Sun

Effective leaders express strength not by suppressing doubt, but by integrating it. Boyd encourages actors playing kings to appear initially burdened. “Let the audience see the weight pulling them down.” But a credible leader must transition to vitality, authentically. Ultimately, “You understand your position and can look anyone in the eye, embodying the human range,” Boyd states.

Charismatic leaders accept their flaws. Boyd helps actors build confidence by exploring personal failings. “Dramatize moments of incompetence. Audiences root for the underdog, but vanity tempts shame. I aim to dismantle these embarrassments.” He might ask an actor to perform something obscene or demeaning in rehearsal to confront their shameful aspects.

Richard II embodies this complex leadership soul. Yeats admired Richard II as his favorite Shakespearean character: initially a flawed, self-absorbed leader who ultimately relinquishes his crown. Boyd advises, “Become Richard II, but play him strong, not weak.”

The play begins with Richard’s abuses of power, leading to his deposition by Bolingbroke (Henry IV). Richard eventually accepts his fate, realizing abdication is best for the kingdom. He achieves a poignant peace, contrasting with Bolingbroke’s burdened ascension.

Queen Elizabeth I reportedly said, “I am Richard II, know ye not that?” late in her reign. Whether referencing fears of assassination or something deeper, her composed rule amidst turmoil suggests she found self-possession in Richard’s example, allowing her to play her queenly role. Like a setting sun, Richard II, in his decline, reveals a different kind of powerful beauty.

Charismatic Cleopatra: A Leader Compared to a Force of Nature

Shakespeare’s later plays shift focus from kings to women leaders. Characters like Cordelia and Cleopatra teach men about humanity and leadership. This shift might reflect Shakespeare’s personal experiences after his son’s death, leading him to spend more time with his wife and daughters.

How to portray a leader who is both deeply human and politically strong? Consider Cleopatra, the heroine of Antony and Cleopatra, which T.S. Eliot considered Shakespeare’s finest work. Tina Packer’s portrayal of Cleopatra highlights this charismatic queen.

Packer, founder of Shakespeare & Company, played Cleopatra in her late 60s, exceeding Judi Dench’s previous record. Dench initially hesitated, fearing she’d seem inadequate as the seductive queen. However, both Packer and Dench proved age enhances the portrayal of Cleopatra’s wisdom, maturity, and allure.

Watching Packer’s rehearsal, parallels to Hillary Clinton emerged. Initially, Antony overshadowed her, but Packer gradually commanded attention, becoming the performance’s center.

Cleopatra exudes charm. She embodies leadership as a “freewheeling, iconoclastic, joyous role,” as Harold Bloom described her, “the most vital woman in Shakespeare.” Despite Roman conquest, she resists despair, embracing pleasure and enduring Roman rule. Antony is captivated.

Cleopatra understands the significance of her losses. She represents Hellenic ideals against Roman legalism. Antony, weary of war, seeks the Hellenic world of beauty and culture she embodies. She champions beauty against law, a courageous stance even on stage. Like a force of nature, Cleopatra’s charisma is undeniable and transformative.

In the coming decade, institutions must embrace mature women leaders. As baby boomers age, women’s influence grows. They age more slowly and remain strong longer. Often seen as outsiders, they excel in leadership, managing states, people, and legacies, like Cleopatra, while valuing the “unmanageable, pleasure-seeking life force.”

Good-to-Great Leaders: Shall I Compare Thee To A Timeless Concept?

Henry V, Richard II, and Cleopatra are powerful leaders due to their complexity. Neither purely good nor bad, they transcend imperfections in service of duty without losing humanity – good-to-great leaders, mirroring Jim Collins’ company concept.

Alison Bomber distinguishes leadership styles through language. Evil characters like Henry IV and Richard III use “crunch phrases,” their language “tastes bad.” Benevolent rulers like Henry VI have “soft and open” language, full of vowels, lacking harsh consonants, beautiful but powerless.

Good-to-great leaders require “courage, space, and confidence to start and speak slowly. Time belongs to you. Great leaders even move slowly. Richard II speaks every word deliberately, wanting to be seen.”

Time, Bomber emphasizes, is key in Shakespeare, pronounced time-uh. “Breathe out fully to inhale deeply. This grounds the breath.”

Shakespeare’s greatest leaders are vulnerable, not grandiose. Richard II in RSC’s production removes his regal attire to reveal a smaller, radiant, human figure. He surrenders power to embrace humanity, achieving a greater majesty. Audiences respond to this authenticity, even if artifice, recognizing a genuine persona.

RSC trains actors to reduce tension, as audiences subconsciously read tension. Tension creates distrust. Bomber recommends “belly breathing” and jaw release. Realizing our mouths are less open than we perceive helps release tension.

In an increasingly pressured world, we need leaders who understand power’s price, exercise it responsibly, and value doubt, harmony, and beauty. We may need to cultivate these qualities within ourselves. Henry V, Richard II, and Cleopatra offer a language and framework for leadership. Perhaps CEO candidates should memorize and recite these roles in interviews. For aspiring leaders, let these inner sovereigns transform us.

Reprint No. 07402

Author profile:

Harriet Rubin ([email protected]) was the founding editor of Doubleday Currency. She is the author of The Mona Lisa Stratagem: The Art of Women, Age, and Power (Grand Central Books, 2007) and The Princessa: Machiavelli for Women (Currency, 1997). Her article “CEO Libraries Reveal Keys to Success,” mentioned on page 124 of this issue, appeared in the New York Times, July 21, 2007.

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