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Coronavirus disease 2019 (COVID-19) is currently ravaging health systems across the world. Psychiatric trainees are at risk of exposure to patients with COVID-19 given their clinical roles in emergency and inpatient psychiatric settings. This article represents a case study of group dynamics in which we reflect on our own experience as psychiatric residents at a Boston-area hospital system in the era of COVID-19 and apply Wilfred Bion's concepts of the “work group” and the “basic assumption group” processes of group operation. We assess dynamics between trainees and administrative leadership both at baseline and in the current pandemic. Since navigation through crises is more effective if group leadership recognizes and responds to basic assumption behaviors, we propose suggestions to enable health system administration to successfully lead health care organizations through periods of societal turmoil. We posit that these principles apply across settings, specialties, and provider types. In addition, we use our observations to indicate future directions for expanding Bion's theories in the contemporary context.