Traditionally, bureaucracy and centralization in relation to the administration and management aspects characterize the Greek educational system. The study of the role of school mentors {school head teachers) should be one of the most interesting studies, linking the past with the future of greek education. The precise description of the role from the government in the year 1985 and the change in the year 2002 could mean that the role maybe is different at the beginning of the 21th century in the educational system. The study examines the greek educational system thought the social -politics and historical perception at the end of the last century. Our research focuses on the study of the role in relation to specific aspects, duties and perspectives. We emerge the factors that affect as school, relations between heads and colleagues etc in the growth of possibilities and faculties of them to manage in the educational system. Every offers a definition what means «management», who faculties lead to the success, their confrontation from the historical social environment as well as practical advices for that it should are encouraged the new teachers, so that they claim places of power, avoiding stereotypes.