The supervision relationship is a primary location where supervisors can engage meaningfully with supervisees about issues of race and culture. This paper explores how supervisors navigate this terrain by offering an analysis of interviews conducted with nine South African supervisors, themselves occupying a range of identity positions and working with supervisees who also occupy a range of identity positions. It is important to hear the voices of supervisors in this context: supervisors are tasked with the responsibility to provide guidance and to help supervisees work through their anxieties about racial and cultural dynamics. Aside from their voices of authority, this paper argues for the importance of hearing the more tentative, ambivalent, or anxious voices of supervisors. These alternative voices infused interviews and offered glimpses into experiences of struggle and discomfort. We suggest that exploration of these more conflicted experiences offer supervisors a pathway towards, rather than away from, authenticity in the supervisory relationship.