This paper arises from a Kenyan headmaster's personal observations of U.S. principals. As a case study, it provides an analysis of U.S. educational leadership by comparing the roles of U.S. principals and Kenyan headmasters. Similarities and differences in roles are noted as they emerge from the values of the two cultures. The impacts of the different approaches to school leadership are considered, especially as they allow for insights into potential alterations in the practices of U.S. principals. The paper concludes with a series of recommended strategies for change in school leadership, which answer the needs identified in the current literature on educational reform.