<p>In <i>The Prince</i>, Machiavelli presents a set of generalisations about leadership that he has derived from his experience and scholarship. His concept of leadership is aligned with that of formal organisational leadership, and is therefore more narrowly focused than much modern leadership literature, which also brings the concepts of informal and egalitarian leadership under its aegis. Having been written long before many of the assumptions that have accumulated around modern leadership publications, Machiavelli provides a fresh and realistic view of formal organisational leadership whose insights have value for modern business leaders. He identifies what he refers to as the virtue of a good leader but, by contrast with modern usage, his idea of virtue concerns leaders’ energy and will to do whatever is needed to accomplish their goals. He makes the case that most leaders have a particular cast of mind, which causes them to lead in fixed, unvarying ways, and makes it difficult for them to adapt to changing circumstances. Thus, leaders are likely to be successful only when they encounter circumstances that suit their particular kind of virtue. And even then, unforeseeable ill fortune that they cannot guard against may frustrate their endeavours. Much leader-centric organisational research presumes too much for the salience of leadership in explaining organisational outcomes, and pays too little attention to the contexts in which leadership is exercised, the processes over time whereby leaders carry out their work, and the unforeseeable events that can overturn the best leaders’ plans.</p>