This article describes a self-reflexive exploration of five instances of encounters with indigenous managers that challenged my preconceptions about management. My focus is on the praxis of the moments in which these challenges occurred. I analyze these experiences to answer four questions: How did learning occur? What was that learning? How did it influence me? What might be the implications of this analysis for management education? My examples are drawn from two research projects with managers and students working in the nongovernmental organization sector in India and the United Kingdom. The encounters that I describe have been characterized by an initial experience of surprise and disorientation, followed by increasing awareness of new ways of conceptualizing the tasks of management. Along with Said, I suggest that developing the capacity for attending to surprise, as a means of "decolonizing the imagination" should form a significant element of management education for both teacher and student. Finally, I draw on my experiences as a teacher to offer some suggestions on incorporating surprise into management pedagogy.