Literature (Foster, 2004), agrees that there is a relative absence of research that documents the experience of male and female headteachers leadership in relation to school improvement. This qualitative life history study explores a male and female head teachers' experiences of leading school improvement in two secondary schools of Azeem Education System, Northern Areas of Pakistan. Semi-structured interviews, observations and document analysis were the main source of data generation. The study revealed that the context of leadership and school improvement are relative and are influenced by the contexts of a school and the communities in which the school is situated. The needs, demands and future trends as viewed in these contexts shape and guide headteachers' leadership practices and their school improvement efforts. So, an explanation of headteachers' experiences of leading school improvement also needs to be taken into account not only their personal skills but also to see, how well they were able to respond to the school context. Studies showed that gender may play an important role in teachers' ascend to headship. Male teachers have better chances to avail headship position due to their better academic qualification. While female may need to struggle longer to achieve better academic and professional credential in order to prove their ability of assuming headship position. In order to enhance headteachers' efforts in leading school improvement, some recommendations to the organization were made, that the organization needs to acknowledge headteachers' diverse leadership practices for school improvement. This also requires recognition of headteachers' unique life histories (personal and professional), which shape and guide their unique perceptions and practices of leading schools for improvement. In this connection, the study recommends that professional development programmes for headteachers may include life histories of the headteachers, in order to understand their perceptions and practices of leadership, particularly in the context of their efforts to school improvement.