Recent research designed to advance understanding of educational leadership has described principals’ lives as beset by dilemmas. Drawing on studies of teachers’ dilemmas, researchers in the United States, Australia, and the United Kingdom have investigated the dilemmas faced by principals in an educational reform environment fraught with uncertainty and contradiction. By contrast, little research has been conducted on dilemmas faced by Hong Kong principals. The shortage of empirical work in this area is indicative of a more widespread neglect of investigation into principals’ lives in non-Western English-speaking contexts. Dilemma research conducted purely in such contexts disenfranchises large groups of principals, denies the identities of important racial, ethnic, and national groups, and risks restricting understanding to narrowly, even arrogantly, defined parameters. While the area of organizational culture has been researched extensively (e.g., Bolman & Deal, 1991), little work has been conducted into the influence of societal culture and context on leadership, organization, and management. This chapter purports to partly address this situation by investigating the role dilemmas play, or do not play, in the lives of a small group of Hong Kong principals.