Participant supervision is a unique application of live supervision in which a supervisor and supervisee see clients conjointly. Although minimally discussed in the family therapy literature, it has notable advantages, chief among them being a shared clinical experience that increases attunement to supervisee skill and development, the modeling of skillful intervention, and a higher degree of collegiality. However, it is not without its challenges, including supervisee vulnerability and anxiety, diffusion of responsibility, and limited time for case discussion. This article highlights the experience of one supervisor and three doctoral‐level supervisees engaging in participant supervision over the course of a 2‐year period. Using illustrative examples, we discuss our experience of the advantages and challenges of participant supervision, and provide recommendations for establishing a collaborative relational context within which supervisory benefits can be maximized.