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This article explores the dynamics of racial and cultural enactments within the supervisory encounter. The recognition of racial and cultural issues in clinical supervision is an essential clinical competence. Those supervisors who are culturally and racially different from their supervisees and their patients need to integrate both an understanding and sensitivity to cultural and racial difference. This has implications for psychotherapy training and the provision of services to those who present as different. The author presents some clinical case examples of group supervision and discusses how issues around difference may be recognized, understood, and worked with in the supervisory situation. The author illuminates some interferences and conflicts within the dynamics of a group supervisory situation that manifested itself either in the supervisee or in the supervisor thus threatening the supervisory task. The author calls for a more explicit discussion of difference specifically within the supervisory relationship, and challenges the Eurocentric authoritarian prescriptivism towards subjective experience.