This is a qualitative study that explores the strategies used by a woman principal to build a successful high school. Despite the plethora of gender supportive policies in South Africa women are still underrepresented in school management positions. Those who do shatter the glass ceiling face gender discrimination resulting from societal and cultural stereotypes. This study aims to tell the story of a woman principal who battled social, patriarchal and institutional odds and still succeeded as a leader. The findings reveal that the principal relied on her womanly attributes of caring, empathy, knowing the community and involving parents. In demonstrating support for the community in which she worked and in having the courage to care she was able to transform her school. This study shows that caring is a form of power. She is a transformational leader who managed to change the school culture from being dysfunctional to being successful. Collaboration and staff development are the other strategies that led to the success of the school managed by Debra, the woman principal in this study. Narrative inquiry as qualitative research approach was employed in order to explore the experiences of Debra, as the principal in this study is named. Purposive sampling was used for the selection of the participant. Data was collected by means of in-depth and semi-structured interviews supported by school documents. Transformational Leadership Theory, as described by Bass (1999), provided guidance for conceptualizing and analysing the leadership strategies used by the principal. The transformational leader promotes followers' innovation by considering their developmental needs while providing support and coaching through charisma, inspiration, intellectual stimulation and individualised consideration. / Dissertation (MEd)--University of Pretoria, 2016. / Education Management and Policy Studies / MEd / Unrestricted