Within Canada, the ever-changing context of universities is paralleled by an increased number of unfinished presidential mandates, approximately 16 in the past ten years. “Never has Canadian university presidential leadership been under greater scrutiny than it is today” (MacKinnon, 2004, p. 132). The trend of an increasing number of unfinished mandates of university presidents in Canada leads to some important questions that require further exploration. Through an in-depth series of interviews with six of the 16 Canadian university presidents with unfinished mandates, this research dives deeply into leadership experiences and highlights patterns and trends within the individual trajectories leading to their shortened mandate. More precisely, the leaders’ transitional process within their presidential role is examined in order to gain insight into the challenges of transition, particularly for the person at the top of the organization. The findings are focused on the themes of board governance and communication, university transitions, relationships within the executive team, the role of the predecessor, and diversity and leadership. This dissertation contributes a unique piece of research to the higher educational literature, and also provides concrete recommendations to improve transitional practices for leaders within the higher education environment.