This paper reports on a study that explored eductional reform in the secondary sector in Trinidad and Tobago (T&T) by analysing the Ministry of Education's policy documents and examining perspectives on the impact of the current reform agenda from the point of view of practitioners: school supervisors, principals, and teachers. A qualitative interpretive research design was used, which employed a range of data collection methods including questionnaires, document analysis, and interviews. The paper argues that a different, more inclusive and participatory approach to leading context-specific school improvement is required for policy initiatives to be successful. An evidence-based model that takes this approach into consideration is proposed. The model, though premised on findings within the T&T context, can be applicable to other contexts.