This phenomenological study explored the experiences of five women in leadership positions at Michael University, which is a federal higher institution in Southeastern Nigeria. I embarked on this journey because of my interest in understanding how women who have broken the “glass ceiling” (Yukl & Gardner, 2020) experienced leadership at the studied institution. The theoretical framework for the study was guided by Joan Acker’s (1990) theory of gendered organizations. According to Acker, one of the processes in which organizations are gendered is through divisions of labor between men and women, including institutionalized means of maintaining those divisions in institutions. Further, Williams et al. (2012) indicate the theory of gendered organizations is used to explain the persistent gender inequality in the workplace, especially in issues relating to leadership. In addition to gendered organization theory, leadership theory was used as a theoretical framework for the study. The study employed phenomenology as research methodology and snowball sampling was used in recruiting the five participants. In addition, in-depth one-on-one semi-structured interviews was used in data collection and a thematic approach was used in data analyses and interpretation. The findings of the research revealed the participants had both positive and challenging experiences as women in leadership positions at Michael University. In addition, the study found that factors such as culture, gender roles, inadequate education/training, and family responsibilities continued to undermine the progress of women into leadership positions at the institution. The implications of the findings of the study for leadership policy development and practice at Michael University as well as the suggestions for further research and recommendations arising from the study are discussed.