In the history of school management and leadership in the Caribbean, the principal has been the primary focus in the work of educational researchers. Over a decade ago, Trinidad and Tobago began its second major reform of its educational system. As part of the Secondary Education Modernisation Programme, school-based management was introduced and with it a restructure of the organisation of secondary schools that included the formal appointment of middle managers. This study focuses on the beliefs and values that shape and influence the practices of middle management in secondary schools in Trinidad and Tobago. In my exploration of their beliefs and values, four participants took part in one of the few studies conducted on the middle management in the secondary school in the country. By middle management I refer specifically to the Heads of Departments and Deans who are intermediaries between the senior management-Principal and Vice-Principal, and staff. For the theoretical framework, I chose Kamau Brathwaite's "The Inner Plantation." As educational institutions become more homogeneous and tied to global economic plans for expanding markets, the choice of a theory that has the potential to expose the ways in which secondary school middle managers are co-opted into feeding the global economy by the imposition of a market-driven model of school leadership and management is timely. To explore the beliefs and values of this tier of management, I employed the life history methodological approach as it offers a perspective of the major changes in an era of reform that have affected and continue to affect them, from their lived experience of a devolved version of school-based management. Based on this study, the Heads and Dean, resist the overseer role imposed upon them as they seek to live out their beliefs and values in their daily practices as advocates.