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This paper examines perspectives of high school principals in Jamaica and how they make sense of their leadership praxis. This qualitative study brings into focus experiences of school leaders in low income countries such as Jamaica that are not fully represented in the extant literature, drawing on narratives of secondary school principals in traditional and non-traditional high schools. Findings reveal a) different approaches to leadership b) commitment to community, c) importance of leadership preparation and development, and commitment to curriculum development, Findings have implications for school leadership development to improve student outcomes especially in low income countries, support educators and policy makers to draw on knowledge emanating from those contexts to impact educational and school leadership policy making decisions.