This article uses interview data gathered from school leaders to recommend a framework for school leadership preparation and development (SLP&D) in Kenya. Data were gathered from head teachers and principals about the experiences that prepared them for leadership, the gaps in the existing SLP&D initiatives in Kenya, and how current initiatives could be improved. The findings revealed a lack of clarity with regard to SLP&D expectations among school leaders. However, the personal realities and needs of school leaders influenced decisions about when they took leadership positions, what they considered to be meaningful SLP&D, and the modes they preferred and engaged in. The need for a holistic approach to SLP&D was evident in the interconnectedness of: (a) their subjective realities, such as motivations and life commitments; (b) activities they engaged in for meaningful SLP&D, such as taking courses, gaining experience as they moved through the ranks, and mentorship; (c) what they considered to be the requisite competencies for school leadership; and (d) the systemic policies and practices they thought were essential, such as recruitment for SLP&D, standards, accreditation, funding, and partnerships. The article argues for a formalized SLP&D framework that embraces both the personal and contextual realities of the school leaders, the communities they serve, and the systems within which they work.