Nowhere in the world has gender equality been fully achieved. Even in countries that rank highest in the world on globally accepted gender equality indices, the gender gap in areas such as economic outcomes and political empowerment remains significant. This is compounded by the increasing invisibility of the barriers that prevent gender equality from being achieved in all spheres of life. Therefore examining the factors that might prevent women from taking up higher management positions in education is critical for developing appropriate policy options for ministries of education to improve gender equality at middle management and leadership positions. This publication addresses the concern of the UNESCO International Institute for Educational Planning (IIEP)that much of the currently available research on gender in education has limited its focus on gender equality to access to primary and secondary education. The research therefore investigates the 'labyrinth' that women must navigate on the path to senior leadership positions in ministries of education in Argentina and Kenya and offers generic strategies for overcoming these barriers.