International research has indicated, inter alia, that headteacher’s leadership skills are crucial for quality and effectiveness of educational organizations, in both primary and secondary educational level. The paper discusses issues involved in headteachers’ duties and responsibilities and demonstrates perspectives of educational leadership within school units in Greece. It does so with specific reference to the findings of a long-scale, nation-wide research that focuses on educational management and leadership in Greek primary and secondary education. Data derive from questionnaires that have been completed by Greek headteachers depicting their self-concepts and viewpoints about school management and leadership and their own role within the specific (highly centralized) educational system and institutional framework. Data analysis reveals different forms of duties (administrative, managerial and pedagogical) and specifies the time allocated to the aforementioned duties by headteachers. Specific conclusions are drawn in regard to their perceptions on their workload, time management and overall effectiveness. Indications for training needs are also given. Moreover, the research examines the role of the school leader in facilitating communication and interaction with stakeholders in education. Finally it addresses the links and interconnections between theory and practice in educational leadership and illustrates distinct characteristics of educational administration and management in Greek primary and secondary education.