This is a comparative analysis of leadership related to organizational culture and change that occurred at a large Canadian university during a twenty year period 1983-2003. From an institutional development perspective, leadership is characterized as a culture creation and development responsibility. By centering on the tasks of learning culture, this case study compared the challenge of leadership in two very different and competing organizational contexts. Using an experiential narrative and Constructionist approach, this research builds upon the work of Schein. This approach offers pragmatic insight into concepts such as "trust" and "psychological safety" that are often abstracted and ambiguous within organizational theory.