This study sought to investigate the factors that influence school planning in Community High Schools in Solomon Islands. In particular, it examines principal's perceptions of having worked with school plans. While the international literature focuses on school planning and the planning process, much of this literature relates to western contexts which are sometimes irrelevant to the context of a developing nation such as the Solomon Islands. Thus contextual specificity is an important underlying factor in the study. This qualitative research gathered the stories of community high school principals on Makira Island through semi-structured interviews. These interviews were analysed on a case by case basis and then analysed using a thematic analysis approach. While school planning is critical for schools, this study showed that most principals in community high schools in the Solomon Islands do not have the confidence to formulate, implement, and successfully evaluate a school plan. Key findings of this research include the urgency of providing professional development and ongoing support for Community High School principals, the role and priority of interpersonal and school-community relationships, the critical importance of school planning as a process, and the notion of seeing a school plan as a working, living document that supports the activity and development of a school. Amongst the implications from this research is the need for current and future school principals to undergo professional development which is geared towards improving principal's understanding and skills in school planning. A thorough understanding of the essential elements of the school planning process, alongside ongoing support, will greatly enhance current and future community high school principals' capacity to improve planning in their schools.