In South Africa, women are at a high risk of discrimination and opposition to authority when they obtain leadership positions, especially in education (Gouws & Kotze, 2007). The purpose of this study was to inquire into 10 secondary school educators’ perceptions of female principals’ effectiveness in two South African schools. Qualitative case study research methodology included interviews, as well as participant observations and semi-structured interviews. These interviews were conducted within two school settings in South Africa. The participants were teachers, department heads, and deputy principals. When the data were analyzed, it was found that all participants wanted a leader who was transformational and there was a strong preference for those who had feminine traits. This research showed the strong desire for transformational leaders as well as how feminine characteristics are not only starting to become more accepted, but also are now becoming preferred.