The critical role of the school leader has received considerable attention in the school reform agenda over the last several years. Recently English headteachers have encountered increased scrutiny and increasingly complex jobs as greater accountability has been emphasized. The headteacher’s role in school improvement and the changing nature of the role suggest the need to investigate how new school leaders learn their jobs, i.e., their socialisation to the leader role and the outcomes of this learning for school reform issues. This investigation of the socialization methods and outcomes of new English headteachers used a qualitative design with multiple case studies. The study focused on four new headteachers who were all current headteachers of primary schools in the same local education authority in England. Data were collected using standard qualitative methods of interviewing, observing, and document analysis. Three on-site interviews with each headteacher were conducted during the first year of interviewing and a fourth interview was conducted during the following year. Along with interviews, observations were conducted of each headteacher’s behavior in staff meetings; impromptu conversations with staff, students, and parents; parent meetings; and board of governors’ meetings. Documents included newsletter and public relations materials, materials distributed during meetings, and annual reports. In addition to an identification of the socialization methods and sources for these new headteachers, the paper and presentation will identify the personal, role, career, and organizational outcomes of their socialization. The paper will also discuss implications for leadership role and development in a complex reform context.