The issue of training psychologists to become competent supervisors has only been clearly articulated in the past two decades. In this article a rationale for training supervisors in a group format is given. Then, a supervision of supervision group is presented that the authors co-led with two successive cohorts of four predoctoral interns in a large university counseling center as part of its training program. The authors focus on the need to attend to group process and relational themes. Finally, the authors discuss the inevitable boundary concerns that emerge given the multiple levels of relationships that exist among several tiers of trainees and supervisors.