From Jesters to Late Night Hosts: Why Leadership Needs Criticism

Modern jesters: Jimmy Kimmel and Stephen Colbert

In medieval courts, the jester could tease the king. Sometimes it was brilliant, sometimes just cruel, but the point was that someone could say what others wouldn’t.

We still have jesters. But in the USA, Stephen Colbert’s Late Show was recently cancelled, with its final episode scheduled for 2026. Two days ago, Jimmy Kimmel’s show was indefinitely suspended.

Here’s what I keep coming back to. The occupational hazard of leadership is narcissism. Power invites it. And the only real antidote is criticism. Sometimes fair, sometimes not, but without it, narcissism grows unchecked.

I know this in a small way. I teach leadership, and I’ve caught myself hesitating to step into roles because I wasn’t sure I could handle the sting of criticism. That’s why I admire my students in politics or business who take it on anyway. They live with that sting every day.

But if you accept leadership, especially political leadership, you play a dangerous game if you don't protect your critics. Silencing them tells everyone else to protect your ego instead of speaking the truth. And once that happens, the temptations of power become even harder to resist.

Lao Tzu wrote: When the best leader’s work is done, the people say it happened naturally.
To me, the real measure of leadership isn’t how loudly you’re cheered. It’s whether you can keep listening when it hurts.