A recently announced government initiative for educational reform in Cyprus has set school autonomy high on the agenda. This article aims to throw more light into this effort, while localizing the intention for decentralization within the context and peculiarities of the Cyprus educational system. In particular, this article outlines the challenges arising for school leaders, when the reform moves towards implementation of the trends under discussion. In the light of the relevant literature, this article proceeds to recommendations; specifically, the role of school leadership with regards to the establishment of accountability as well as the reform of the organisational culture at the school level.