Come TREK With Us

Overview

Shakespeare’s plays tell the stories of some of history’s greatest leaders, capturing their triumphs—and their failures. In language unmatched before or after, he portrayed how to inspire people, navigate conflict, and make the most difficult of decisions. It is no surprise that his works continue to shape leadership thinking today: books such as Shakespeare in Charge: The Bard’s Guide to Leading and Succeeding on the Business Stage and The Bard & Co.: Shakespeare’s Role in Modern Business testify to the enduring relevance of his insights, while his greatest speeches remain studied in leading MBA programs worldwide. 

This Executive GlobeTREK Leadership Sabbatical takes participants directly into Shakespeare’s world. Across a 10-day journey, executives will watch his most famous plays performed at the Globe Theater in London and in Stratford, where Shakespeare was born. Through conversations with actors and directors, along with reflective dialogue among participants, leaders will explore how Shakespeare’s characters illuminate challenges that resonate in boardrooms today. Beyond his plays, participants will also discover Shakespeare as a savvy entrepreneur who thrived not only in theater but also in real estate—a multidimensional leader in his own right.

Why London and Stratford-upon-Avon

London provides the stage where Shakespeare built his career not just as a playwright, but also as a bold entrepreneur. Here, he co-founded the Globe Theatre, mastered the use of print for rapid distribution, and demonstrated how creativity and commerce can intersect. London’s dynamic mix of history, scholarship, and contemporary leadership voices makes it the ideal setting to explore Shakespeare’s business acumen, his command of language, and his enduring relevance for today’s executives. 

Stratford-upon-Avon, Shakespeare’s birthplace and final home, embodies the roots and legacy of the man behind the works. This setting highlights how personal origins, values, and community connections influence leadership identity. Today, it is also home to the Royal Shakespeare Company, where his words continue to be brought to life.  

Together, London and Stratford-upon-Avon create a powerful setting for exploring both the artistry of Shakespeare’s language and the multidimensional leadership lessons his life continues to inspire. 

What You’ll Experience

As we stand in the Globe Theatre, we follow in the footsteps of Shakespeare and find ourselves immersed in the world of drama, ethical dilemmas, and leadership.  As we interact with world-class actors, directors, theater professionals, and entrepreneurs, participants will:  

Explore Shakespeare as an entrepreneur by visiting the Globe Theater and examining how he leveraged publishing, speed to market, and property ownership to build his career. 

Engage with scholars and practitioners from universities and cultural institutions, gaining fresh insights into leadership, communication, and influence. 

Strengthen executive communication by drawing lessons from Shakespeare’s most powerful speeches and applying them to modern leadership challenges. 

Reflect on personal leadership brand through structured writing exercises and simulations that connect Shakespeare’s words to professional contexts. 

Experience Stratford-upon-Avon—Shakespeare’s birthplace and retirement home—and discover how roots and legacy shape leadership identity. 

Learn from performance and practice with activities led by the Royal Shakespeare Company, including using Shakespeare’s language in real-world leadership simulations. 

Examine questions of ethics and values through the lens of Shakespeare’s characters, weighing timeless dilemmas of loyalty, ambition, and justice. 

Objectives: 

Engage in guided inquiry about what fuels motivation  

• Explore the power of language and performance by leaders to inspire others  

• Examine questions of ethical decision-making and values through the lens of Shakespeare’s characters 

• Reframe leadership story by drawing wisdom from one of history’s greatest dramatists. 

• Strengthen their capacity to inspire teams by harnessing the art of language. 

• Gain practical tools from reflective writing, simulations, and dialogue with experts. 

• Apply Shakespearean lessons on communication, persuasion, and influence to executive contexts. 

• Draw leadership insights from Shakespeare’s plays and characters. 

• Connect entrepreneurship, legacy, and cultural context to leadership development.