What Keeps Leaders Awake At Night — And Should It?

It is one of the most common questions asked of chief executives and board chairs: “What keeps you awake at night?” It’s meant to reveal the depth of their leadership, the gravity of their concerns, and the clarity of their strategic vision. The answers vary — from market disruption and regulatory pressure to talent retention, cyber threats, or reputation risk. And yet, for all its popularity, we rarely stop to interrogate the question itself. Should leadership really be a sleepless job? And if a leader is always awake at night, does that point to strength — or to something more…