How can managers prepare for extreme but exceptional events and for the challenge of managing complexity and uncertainty in their daily business? Confronted with the challenge of achieving high and reliable performance in risk-prone, fast-paced, and unpredictable environments, managers and management scholars can learn a lot from the organizing principles of mindful organizing (MO). MO is based on lessons learned from the high-reliability seeking of organizations such as aircraft carriers and nuclear power plants as well as from the analysis of severe crisis events in these organizations. MO provides the guiding principles and proactive managerial mind-set to build collective organizational capabilities for anticipating the evolution of unexpected events and acting resiliently in times of crisis. The paradigm of MO differs from the rationality-based classical management paradigm, takes the complexity and unpredictability of organizations into account, and puts the design of sensemaking processes at the center of managerial attention. This article explores how the managerial paradigm of MO can be used in action-learning management development programs. I explain how to use the staff ride, a qualitative event analysis focusing on individual and collective sensemaking, to illustrate for managers how unexpected events evolve and how to develop collective patterns of mindfulness. (Contains 1 figure and 1 note.)