This research explored the nature and conduct of successful leadership in the context of Cyprus; how policy and school contexts and heads' experience influence headship leadership. The empirical findings of this study draw upon ethnographic methods rooted within the naturalistic paradigm in order to illuminate the complex and dynamic nature of headship leadership in a specific country context. A group often successful heads in urban primary schools of Cyprus was selected. Data was collected through observations, a review of a number of schools' documents and semi-structured interviews carried out with each of the successful heads and with people that had everyday conduct with them. The overall findings provided empirical evidence of the complexity of successful head teachers day-to-day practices and pointed to the positive and negative in themes of 'policy contexts', 'the values of society' and 'school and experience contexts'. These results support earlier evidence on successful leadership but also extend this. The evidence from this research has important implications for head teachers' learning and development and the role of the government in raising standards of schooling in Cyprus.