Within the supervisory relationship, cultural issues tend to focus on the relationship between the therapist–client dyad. This chapter also highlights additional aspects of the triadic relationship: supervisor–supervisee, supervisor–client, and systemic differences between supervisee–agency, supervisee–community. Culturally aware supervision has been explicitly discussed in the supervision literature; we expand how supervisors in art therapy can further this endeavor. An emphasis is made on encouraging the supervisor and the supervisee to intentionally name differences. To help with this undertaking, we propose helpful ways of broaching difference, and tips on how to encourage dialogue if a supervisor or supervisee is not ready to talk about such differences. In this chapter, cross-cultural supervision is discussed in terms of visible minorities (e.g., race and gender) and differences that are often more hidden (e.g., sexual orientation, religion, disability). Feminist and critical race theories are employed to support the supervisor and supervisee in conversations surrounding power and difference. This chapter includes clinical supervision vignettes by the first author and two different supervisees, and arts- and writing-based practice prompts for supervisors and supervisees to build the groundwork for future conversations about cultural dimensions of work with clients.