This research explores the constraints experienced by island school leaders in implementing changes in their schools to improve the quality of education in the Maldives. It examines educational leadership in a developing country that is striving but struggling to meet global educational goals and build on its indigenous roots. The aim is to evaluate educational change rooted in Western ideology against that rooted in the unique culture of the Maldives, considering the perceptions of Maldivian head teachers. The primary concern is to give a voice to Maldivian school leaders and their perspective on the constraints they meet. To understand this fully, it is also necessary to look at the perceptions of other stakeholders and the interactions between them.