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 worrying beneath the surface?

The Power Behind the Question

The question is powerful because it strips away the formalities of strategy documents and board reports. It goes straight to the heart of leadership consciousness. A CEO’s response often reveals what truly matters to the organisation and what occupies the space between success and failure. But there’s another way to interpret it: what keeps a leader awake is often what the governance systems around them have failed to anticipate, mitigate, or delegate. In that sense, the question can expose as much about organisational weaknesses as it does about leadership priorities.

When Sleeplessness Signals a Deeper Problem

If sleeplessness is a constant companion, it may not be a badge of honour. It may instead signal that too much is centralised in the leader’s head. It might suggest that risk frameworks are inadequate, delegation is poor, or the board is not providing sufficient strategic oversight. It might even indicate that there is no clear succession plan, that organisational culture is weak, or that decision-making is reactive rather than proactive. Good governance is supposed to enable leaders to sleep — not keep them awake.

The Right Kind of Restlessness

Of course, no leader will ever sleep entirely soundly. Leadership is, by its very nature, a burden of responsibility. There are questions that should cause discomfort even in well-run institutions. These are the questions of purpose and legacy: Are we still solving the right problems? Are we creating value for stakeholders in a rapidly changing environment? Are we building a culture that outlasts individual personalities? Are we preparing the next generation to take the baton forward? Healthy restlessness around such questions is a sign of maturity, not dysfunction.

Governance That Lets Leaders Sleep

But sleepless nights over issues that could have been prevented — like repeated operational crises, compliance breaches, or predictable financial shocks — point to governance failures. Boards exist precisely to create the conditions where leaders can focus their anxiety on the future, not the past; on strategic direction, not daily firefighting. When systems of accountability, internal control, risk oversight, and decision-making are strong, the nature of what keeps a leader awake shifts. It becomes less about fear and more about foresight.

Leadership Maturity: Peace of Mind, Not Panic

The most effective leaders are not those who never sleep, but those who sleep well because they have built institutions that can function without them. They design governance systems that anticipate risks before they become crises. They invest in people and structures that enable decisions to be made at the right levels. They empower management teams to execute without constant supervision. And they cultivate boards that both challenge and support, creating the confidence to look beyond the immediate horizon.

Perhaps then, the real question is not “What keeps you awake at night?” but “What have you put in place so that you can sleep?” Because leadership that is perpetually anxious is not necessarily leadership that is effective. It might be leadership trapped in a cycle of short-term crisis management. And governance that leaves leaders awake every night may not be governance that is doing its job.

In the end, sleeplessness is not a sign of dedication — it can be a sign of dysfunction. Leadership maturity is measured not by how many hours a leader lies awake worrying, but by how deeply they trust the systems, people, and governance structures around them. If leaders must stay awake, let it be to dream of the future, not to fear the present.

Max Manzi is a Chartered Governance Professional & Advocate, currently serving as the Chief Governance & Legal Officer at aBi Finance Ltd, a wholesale impact finance solutions provider, catalysing the transformation of Uganda’s agricultural finance ecosystem.