To be successful, leaders must understand the people they lead and the complex nature of the environment within which they function. Such contextual knowledge influences leadership styles and behaviors. While research has shown that intrasocietal contextual differences are associated with different styles and different degrees of effectiveness of leaders, it may be that cross-national contextual differences are even more significant. To gain a deeper understanding of such differences, the authors examine how leadership styles and effectiveness are conceived by principals and other senior educators in Trinidad and Tobago and compare such conceptions with those documented in the literature that is focused on Western, more industrialized societies. (Contains 7 footnotes.)