The current focus on instructional leadership within a high stakes accountability environment has frequently ignored the political role of school leaders. This article examines the perceptions of a group of new English headteachers to determine the features of their political role and their process in learning this role. The investigation is part of a larger study of new headteacher socialization that used a qualitative design with multiple case studies. The study found that these new headteachers confronted internal political issues, such as weak teachers, staff conflicts, resistance to change, and conflicts with parents as well as external issues, such as those involving governmental entities, the press, and the union. In responding to these political issues, the headteachers used trial and error, mentors/role models, and information gathering. The article ends with a discussion of the sphere of political activity among school leaders and the tactics for learning how to think and act politically. Implications for leader preparation and future research are also identified and discussed. (Contains 1 note.)