Many Master of Library and Information Science (MLIS) programs are now offered online, and most of these programs offer courses on leadership and management principles. Teaching leadership in any context presents challenges because leadership is a hazy and confounding concept. The intrinsic problems in teaching leadership are compounded by the professional context of libraries; librarianship is a feminized profession whereas being a leader is often a male-oriented construct. This confounding mix of teaching leadership informed by feminist theory is magnified by the challenge of teaching online, where the harassment of women academics (such as MIT's Chris Bourg) is pervasive and destructive. There is a paucity of research and discussion on how to design online leadership courses in graduate MLIS programs that account for these challenges. This paper contributes to this discussion by expanding upon Baldwin, Ching, and Friesen's grounded theory model of online course design and development. Grounded theory is an experiential methodology, and this paper aligns with Baldwin et al.'s grounded theory approach by applying constant comparison between the author's experience designing an online graduate-level leadership course and their model.