A number of researchers have provided an overview of the progress of research focusing on gender and educational leadership/management in the twentieth and twenty-first centuries. Some cast studies of representation as an early phase overtaken by later concern with phenomenological and radical perspectives. More recently, a focus on women and equity of representation within the workplace has been attacked as inappropriately essentialising women or as redundant in the light of advances in gender equality. This paper reviews the purpose and nature of descriptions of gender representation in educational leadership and links to ideological and power flows. It also describes one international effort to make progress in understanding the experience of women school principals within the Commonwealth and explores the significance of the difficulties encountered. (Contains 1 note.)