Although there is an extensive literature across a range of national contexts concerning the evolving role of the school leader, little has been written about the rapidly expanding world of international school leadership. This paper focuses on the top tier of leadership of international schools by drawing on semi-structured interviews with 12 school principals in Malaysia, during which they reflected on the nature of their job and the routes they had taken to headship. It is argued that although the overwhelming majority had taken a school leadership qualification and found elements helpful, they felt that it did not adequately prepare them for their role. Several ways in which international school leadership differs significantly from educational school leadership in other contexts are identified, with principals needing to pay attention to loneliness, transience, cultural differences, governance, business elements, and managing school composition. By identifying key challenges faced by international heads, and by charting the paths that individuals take towards headship, this article seeks to understand the nature of senior leadership in international schools.