The purpose of this paper is to attempt to investigate the factors accounting for the lack of ambition among Greek female teachers in reaching managerial positions in the higher echelons of education's hierarchical structure. The analysis was performed on data collected from 304 female primary teachers during the academic year 1999-2000, randomly selected from 10 Greek prefectures. Statistics and binary logistic regression are used to analyze the determinants of female primary teachers' underrepresentation in school administration. Results suggest that avoidance of managerial responsibilities and lack of encouragement offered by the Greek school administration are among the reasons for the underrepresentation of Greek women in school administration.