Best of…Leadership Essays

A while back, spurred by a question from a leader I work with, I gathered a summary of some of my most read, or “best of…” essays over the last year or two.

Curating a new list for you here, I’ve collected a best-of, most-read, and most-commented essays centered on leadership and the ever-growing demands of leaders in our ever-changing world.

The Paradox of Leadership: To Lead Is to Disappear — because the strongest leaders make themselves less and less necessary, and that notion tends to run against nearly everything modern leadership culture rewards.

Leadership as Curation — because the leader’s real work is less about gathering more input and more about protecting the few things worth zoning in on and carrying forward.

The Confidence Con — because the doubt keeping you (and me) up at night is often proof you’re doing something that matters.

Improv Leadership — because everyone has a plan until, as Mike Tyson said, “they get punched in the face.” All violence aside, our readiness to adapt to the unseen and unpredicted is a decision.

Near Enemies of Trust — because the behaviors that erode trust fastest are the ones that look like good leadership but often undermine what great leadership cultivates.

The Useful Opponent — because a room that agrees too easily has already stopped protecting itself through healthy challenge and debate.

The Art of Better Listening — because being heard changes what people believe they’re invited and allowed to bring into the room.

Who Do We Root For? — because who a leader believes in becomes what the team grows into, whether it’s said out loud or not.

Why Good People Quit—and How to Keep Them — because your best people rarely leave for money; they leave for meaning, which few notice is missing.

Your AI Strategy is a People Strategy — because the technology is (really) never the bottleneck or the silver bullet; the culture and its conditions are always your secret sauce.

A personal note: I’ve spent close to three decades sitting across from leaders having the conversations these ten essays shine the spotlight on, and sketch the outlines of. Most of the leadership growth I’ve watched came from someone getting deeply honest, facing their bright spots and blind spots, and growing their interior game. In a sense, our leadership is about the capability already sitting there, unused, waiting on permission, waiting to be remembered.

If you want a more trusting team, a culture of belonging or a magnetic brand that attracts more of the right customers, I can help. If you'd like to explore if working together makes sense, drop me a line.

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