This case study presents the findings from a qualitative research project about a Black woman scholar, the first non-White female to serve as chair of a department and the associate dean of the college in its 100 year history. The study focuses on the experiences of a Black woman scholar as a chairperson and the learning she achieved during her journey. It also documents the values she held as a leader in an academic environment and the way in which she brought her understanding of culture, her servant leadership, and its implications to bear on the role she negotiated during her tenure. The themes found across the three interviews that were conducted with the subject in the study and the interview with each of her two mentors include the management, challenges, and cultural aspects of being Black and female in a predominantly White work place. This rubric organized the journey of the work life of Willa and her perception of the way in which she navigated the terrain as a Black woman administrator who had to create her own vision of leadership as a scholar.