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Career opportunities will be offered objectively to those who are able to meet the increased demands required by modern times for education, while making it possible for all teachers regardless of their gender to adapt to a constantly changing work environment. Reduced representation of female teachers in educational administration is not new but is a timeless phenomenon both in Greece and internationally. The purpose of this study is to approach theoretically, through bibliographic research, concepts of gender, leadership and analyze stereotypes that result in preventing women from equal participation in educational administration, with obvious effect of their "under-representation". This paper also investigates and those factors that lead to non-administrative claim or management posts of teachers, taking as an example the case of Secondary Education of Pieria. As a methodological tool used questionnaire, through which exploited quantitative data. The questionnaire was structured with closed questions, which sought the personal opinions of teachers, to investigate the issue of the presence of both sexes in educational administration and filled by one hundred and seventy (170) teachers, administrators and non in Secondary Education of the Prefecture Pieria.