This paper explores basic tasks involved in the supervisory process, and frequent problems in carrying out these tasks. Basic tasks include clarification of mutual expectations of supervisor and supervisee; the establishment of mutual trust as fundamental for countertransference analysis; “parallel process” exploration and clarification of explicit and implicit theoretical assumptions by both supervisor and supervisee. Frequent problems include the extent of initial evaluation of patients; problems of intervening “without memory or desire”; transference and countertransference diagnoses and interpretive consequences; clarification of affective dominance; interventive shifts with severe psychopathology, and realistic goals of patient, supervisee and supervisor. Limitations to supervision include specific psychopathologies, cognitive limitations, and a generally restricted capacity for empathy by the supervisee.