There is increasing pressure on small island states to reconceptualize education policies, education management practices and curriculum to address the emerging issues caused by global economic, social and cultural changes. It has generated increasing demands on limited available resources which is further confounded by the often contradictory yet legitimate advice provided by international and local experts. This paper reflects on the changing expectations to provide a critical analysis of the challenges facing education planners in small developing countries. It challenges them to move beyond the stereotypical ways of thinking about education development while acknowledging the role played by previous educational development models.