The purpose of this research is to examine the views of the potential secondary school Headmasters about the legal framework concerning their selection, as it was implemented in 2011. The research was conducted in June, 2011 with the help of 80 candidates out of a whole of 110 who had applied for the position of the school Headmaster in the secondary schools of West Attica. The methodological tool used was a questionnaire and the result analysis was carried out according to the statistical programme SPSS 17.0. It was found that the current framework encourages the most suitable educators to apply for the position and compiles the necessary candidate data through the interview process, their biographical details and the educational seminars. The participants deem it is important that the people selected should be currently in office, also hold the highest rank (A) and have an 8- year teaching experience and administrative skills in the field of education. Additionally, the applicant school Headmasters firmly believe that their role in the existing educational system is fundamental, and the most essential skills they need to have are a clear vision for the future of education and the ability to share it with the members of the school community. There were some different views, however, on issues concerning the gender variables and those that concern work experience in the school field and the managerial position.