This dissertation addresses the challenge of teaching organizational change leadership in executive education programs. The argument is made that these programs have an important role to play in preparing organizational leaders to cope with the ambiguities and paradoxes of change. Experiential learning in executive education has been described as a kind of space of potentiality, separate from organizational life. Organizational change leaders, emerging into awareness of change complexity, seek bounded experiential spaces in which to experiment and learn while engaging with their “real” world. In contrast, the typical business school curriculum often highlights normative and prescriptive change models which downplay or ignore the uncontrollable human and system dynamics that make change so difficult. As a consequence, executive education programs may not fully prepare leaders to cope with change complexities. There has been relatively little research about the construction and use of the experiential domain for change leader development in the executive education setting, particularly over time and beyond the formal program experience. My research focused on exploring boundary conditions that reproduce a context in which participants develop the capacity to sense and work with the hidden challenges of organization change—both in the system and in themselves.