What if the best lessons in leadership came not from success stories, but from characters undone by their own flaws?
That’s the question John Miles, writer, founder of professional development startup Inkpath, and former head of training in the humanities at the University of Oxford, explores as a contributor to The Arts of Leading: Perspectives from the Humanities and the Liberal Arts, edited by Edward Brooks and Michael Lamb.

In this interview, Miles reflects on Shakespeare’s evolving view of power – and how the playwright’s most compromised, contradictory characters might still have something urgent to teach us about what it means to lead.

Read an adapted excerpt from The Arts of Leading.

Your chapter in The Arts of Leading juxtaposes Shakespeare’s early plays with his later work, and highlight how even his ‘bad’ versions of characters offer insights into leadership. What does the evolution of Shakespeare’s writing reveal about his developing thoughts on leadership?

It’s difficult to say much about Shakespeare himself, but the scope of his later plays broadens in comparison.

In the later Folio text of King Lear, for instance, the Fool interjects with a prophecy whose garbled anachronism collapses the whole (epic!) play into a passing moment in history. It’s as if Lear’s leadership and decisions are suddenly inconsequential in the grand scheme of things.

Leaders are considered through a longer lens, just as we all will be as time marches on – no doubt Shakespeare was as conscious of this as anyone else.

Do you think Hamlet’s deliberation could be seen as a strength rather than a flaw in leadership?

Although it is wrapped up in procrastination, Hamlet’s deliberation is also a kind of resistance against his “sea of troubles.”

Everything afterwards is capitulation: to how everyone expects him to act, to history, to the familiar tropes of the traditional revenge hero. And, of course, to our expectations as playgoers – he’s locked inside a fifth act which is as terrible as it is inevitable.

He stops leading and follows. His thinking is his strength. His tragedy is that thinking is rendered meaningless by the play’s end. For a fleeting second, his philosophy imagines a place where being a good person and a great leader aren’t mutually exclusive.



What can we learn from ‘imperfect’ models rather than always aspiring to polished perfection?

It’s easy to see Shakespeare’s characters as moral lessons. But they’re more complex than that – and shaped by their circumstances as much as their flaws.

The challenge is to see these imperfect models as products of their environment. People don’t act badly in a vacuum. Their context matters. That doesn’t absolve them – but it complicates them.