This paper examines the career progress of female principals in Greek secondary schools and the under-representation of women in management positions. Drawing on in-depth interviews with six women principals in Athens, the paper considers the factors affecting women's participation in school management. The findings demonstrate that women are greatly under-represented in secondary school management positions. The main reasons for this disadvantage are personal factors, covert discrimination, gender stereotypes and constraints experienced through their socially defined roles. (Contains 1 table and 2 figures.)