This paper examines the meaning of stepping in and out of the formal supervisory roles and allowing relational unbidden experiences in the supervisory space. Such episodes evolve the supervisory relationship because they help to relieve the supervisees of their sense of aloneness in bearing a burdensome clinical responsibility: they change the supervisees’ perspective on therapeutic processes from first person singular to first person plural. Despite their evaluative function and the professional community that they share with supervisees, supervisors can facilitate the emergence of these episodes with the widely accepted practice of imagining therapeutic interactions. Such activity changes the hierarchy and reduces the tension in the supervisory space, and allows unbidden relational experiences to emerge. Thus, challenging the supervisory framework and temporarily stepping out of the formal roles not only strengthens the supervisees’ ethical clinical position but also allows for productive and creative processes in supervision.