The concept and practice of strategic planning, while entrenched in educational institutions in the West, is just catching on in Kenya. While literature emphasizes the importance of collaborative strategic planning, it does not indicate the challenges presented by collaboratively engaging in strategic planning. This article reports on findings of a study of how one Kenyan secondary school engaged in strategic planning. The study aimed to find out how the various stakeholders in the school are involved in strategic planning. The study adopted a qualitative case study approach. Data were collected through semi-structured interviews and document analysis. Findings show that, although the school stakeholders were involved in different ways in the strategic planning process, the school did not achieve a collaborative strategic plan because the stakeholders approached the process disjointedly. In addition, lack of knowledge about what strategic planning constitutes rendered some of the stakeholders passive participants. Findings illustrate that strategic planning is a concept and process that is challenging for school stakeholders and hence, for contexts similar to the one in which the study took place, there is need for sensitization and training of school stakeholders on the strategic planning process in order to build capacity for schools to reap benefits from it.