This article discusses the value of learning from a psychodynamic approach to experiential learning. This approach is used to help students experience and understand the emotional and relational complexity of leading and managing within organizations. From this perspective, experiential learning means engaging with emotions and with embedded relations of power, to unsettle expectations of how organizations work. Here, we consider the professor’s role, which is to help students work with and through the emotional dynamics generated in work relationships, even when those dynamics are difficult to bear and the overriding impulse is to avoid or defend against them. In this way, students are being supported to better understand how organizations are emotional places, not how individuals within organizations can “manage” emotion.