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This study explores the challenges faced by school principals, in Trinidad and Tobago, and the responses to these challenges as they negotiate the education system to make their schools more effective institutions of learning. The study focuses on system related challenges, and further reviews these challenges within the context of the current educational reform programs. Focus group and interview data from 22 principals and senior educators provide the data for the study. Results indicate that despite the constraints imposed by an overly centralized bureaucratic environment, principals through the use of creative strategies still find it possible to be effective. Emerging from the study is the notion of leadership as a subverting activity and the concept of “centrist leadership.” These conceptualizations of leadership emphasize in the first instant leadership behaviors seen as necessary to circumvent the bureaucratic constraints, and in the second instant, qualities deemed essential for effective functioning in a multi-ethnic, multi-religious society The latter is a concept we intend to develop further.

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