In this article, aspects of postmodern supervision are explored that highlight the blurring of boundaries that occurs between the multiple roles performed by supervisors. An approach to supervision is detailed that shows how a supervisor who navigates between roles can assist supervisees in constructing identities congruent with the stories they tell about themselves as successful therapists. Six of the many possible roles that supervisors play are illustrated through dialogue taken from a group supervision session. In the last part of this article, concepts that inform a postmodern approach to supervision, borrowed from the literature on narrative and constructionist therapy, are discussed.