The practice of supervision is increasingly seen today as a pedagogic activity in which knowledge and skills are transmitted from one party to another. Debates around supervision, however, have historically been concerned with a number of other issues, most notably transference and countertransference. We examine the central arguments of these debates in the psychoanalytic tradition, and discuss some of the theoretical and clinical consequences that follow from them. Taking unconscious dynamics into account forces us to recognize that supervision cannot be seen as a ‘neutral’ exercise of accumulating knowledge, but rather confronts both supervisee and supervisor with significant questions about their own position and self-image.