This qualitative study focused on the successes and challenges experienced by four undergraduate college women while holding top leadership roles in student organizations. Interpretive and descriptive qualitative research methods were employed with aspects of case study and phenomenological approaches of inquiry. Data were collected through one-on-one in-depth interviews, a focus group interview, and participant journals. Results suggest the women’s perceptions of their leadership successes were externally focused, emphasizing the organization and helping develop group members. The challenges faced by the women involved difficulty in balancing relationship and task behaviors, difficulty in balancing the roles of leader and friend, and challenges faced by the larger organizational and environmental context. These findings are examined alongside existing literature. Implications for supporting college women in formal leadership roles are presented, along with recommendations for future research.