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The modulation of an objective process of selecting school directors in Secondary education has been a big issue in Greek reality. From 1976 to 2017, various legislative texts and many other modifications and Presidential decrees have been introduced, concerning the management and mentoring model in education. However, an appropriate required educational policy remains an unreachable goal. It appears that the Greek state has never achieved to legislate a reliable school director recruitment system having the necessary political and educational union consensus.This paper presents a historical review and records the whole Greek legislation (from 1976 to 2017) related to the selection processes of education executives, specifically the school principals. There has been an effort to record and codify the views of a number of educators, who have already been principals in a school unit. Through the historical review, there has been a comparative presentation of the specific laws. There has been, also, a kind of contemplation, in order to point out the defects, the pros and cons of the educational system. In the end, some opinions and aspects are suggested with the ambition that the reader or even the authorities will draw some conclusion for a stable and permanent process. The modulation of an objective process of selecting school directors in Primary and Secondary education has been a big issue in Greek reality.From 1976 to 2018 , various legislative texts and many other modifications and Presidential decrees have been introduced , concerning the management and mentoring model in education. However, an appropriate required educational policy remains an unreachable goal. It appears that the Greek state has never achieved to legislate a reliable school director recruitment system having the necessary political and educational union consensus.. This paper presents a historical review and records the whole greek legislation ( from 1976 to 2018 ) related to the selection processes of education executives , specifically the school principals. There has been making an effort to record and codify the views of a number of educators, who have already been principals in a school unit. Through the historical review, there has been a comparative presentation of the specific laws. There has been , also, a kind of contemplation , in order to point out the defects , the pros and cons of the educational system. In the end, some opinions and aspects are suggested with the ambition that the reader or even the authorities will draw some conclusion for a stable and permanent process The enquiry was based on the views and opinions of educators and principals of school units, still working,. The data was collected with the aid of questionnaire. The results of the research show a great interest. It appears that the majority of the educators are in favour of a permanent selecting system where the criteria- qualities of the candidates will remain stable. It is also remarkable that the majority of those questioned believe that the candidates should be tested by written examinations. Moreover, a high percentage of them consider that a master’s degree or a P.H,D related to the educational administration should take more credits than any other degree. It is impressive the fact that the majority is against the permanency of the position as they believe that this position should be limited in two terms period. They also believe that there should be the participation of the teachers’ association in the evaluation of a principal. In the end, the presence of psychologists or sociologists in the selecting procedure is considered to be necessary.