The recent decentralisation of authority to the community high schools highlights the changing nature and role of school leadership in the Solomon Islands. This study explores the context of school leadership for principals and deputy principals in the community high schools from the leader's perspectives. More specifically, what is it like 'being' an educational leader in the community high schools in the Choiseul province. This study attempts to describe the context of leadership using the leader's accounts of being in this role before and during their current school leadership position. This study was conducted as qualitative research and used a case study research approach. The school leaders of six community high schools of Choiseul province were participants in this study. Eleven school leaders, five principals and six deputy principals, took part in semi-structured interviews about the nature of their leadership context. The research question that acted as a guide to these interviews was: What is it like 'being' a school leader in a Community High School in the Choiseul province? Through semi-structured interviews with each participant, and the documents that were related to the school leader's position and role, the findings of this research raise a number of issues for those in leadership. This includes the impact of the remoteness and isolation that is seen as a major impediment to leadership preparation and ongoing professional development. The findings also showed that school leaders typically experienced an appointments procedure which was influenced by the local community. Since the community high schools were still being physically developed, the school's physical development was seen as a priority when it comes to the appointment. The research findings provide the basis for establishing policies and practices that might support and enable current and future school leaders in Choiseul in the future.