Purpose: The purpose of this paper is to evaluate the quality of the current provision for school leadership in Kenya, the extent to which they have an impact on student outcomes and the return on school leadership preparation and development investment. Design/Methodology/Approach: The paper draws from educational leadership, management and administration courses delivered by universities and other institutions to aspiring and practising educational leaders in Kenya. It employs a method for evaluating return on leadership development investment first articulated by Eacott (2013). Findings: While there is growth in provision, consistent with international trends, this provision is more recognised for its standardisation than points of distinction; there is minimal attention to identified dimensions of leadership leading to higher student outcomes which raises questions regarding the universality of school leadership preparation and development curriculum; and the high course costs of current provision is an inhibiting factor in assessing the return on investment in school leadership preparation and development. Research Limitations/Implications: The study was limited to publicly available documents from a limited sample of institutions. There is a need for more studies in the area. Practical Implications: Institutions seeking to offer school leadership development have grounds on which to make decision about what programs their school leaders should undertake in terms of cost and quality. The study provides institution offering school leadership development courses evidence on which to base future policy direction. Social Implications: The findings provide a case for investing in school leadership development given the impact courses may have on student outcomes. Originality/Value: The paper provides a comprehensive overview of the current provision on school leadership preparation and development in Kenya. It contributes to its understanding in Africa in terms of quality, performance impact and return on investment.