The Leadership Contradiction No One Talks About

The leadership contradiction no one names clearly: we ask leaders to embody uncertainty while designing systems that punish them for it.

First: McKinsey & Company’s study of Fortune 500 CEOs. Superficially, enlightened language: “curiosity,” “learning mindsets,” leaders who “admit they don’t know everything.” But read it again. Even the celebrated vulnerability, “bring your worst self”, is nominally a strategic problem-surfacing to maintain the machine. And even McKinsey can’t quite hide that it’s breaking people.

Second: A piece by about poker players that, inadvertently, maps our entire leadership moment and points out that when the game is life and not just numbers, connection matters more than optimisation.

I return to the tension of connection versus abstraction (again and again, SORRY!) because we need frameworks to see patterns, but when abstraction becomes untethered from the actual people, places, and histories, it loses what makes systems real.

Do we have it backwards?

The wisdom isn’t in doing more, faster, with greater optimisation, but in knowing when the framework helps and when to let it go. The heroic paradigm is collapsing under its own weight. Do we have the language and practice ready for what comes next?

Originally written for LinkedIn on 18 November 2025. View original →