This article is aimed at raising critical consciousness, accountability and empowerment in the supervisory relationship in graduate field education. As more clinicians with intersecting identities navigate rigorous Master's degree programs, there is a growing need for field instructors to utilize cultural humility in their supervision approach and style. In addition, burgeoning clinicians need to be affirmed, empowered and aware of the intra/inter-cultural dynamics inherent in the supervision process, giving specific attention to power and privilege. In order to navigate culturally relevant supervision for new therapists with a level of humility, field instructors and supervisors face a tall order; it is essential they address cultural differences, validate cultural identities and experiences, and explore power, privilege and intersectionality in the supervisory space while concurrently supporting clinical growth. These difficult dialogues require specific skills, self-awareness and vulnerability on the part of the supervisor. As supervisors attempt to initiate this transformative process, it is important to consider similarities and differences in how supervisors and supervisees experience efforts to engage in difficult dialogues. The authors utilized an anonymous online survey to explore the experiences of supervision among supervised clinicians (n=51) and supervisors (n=39). Qualitative data reflect beneficial supervision regarding clinical content, with a consistent lack of discussion and recognition of power and privilege dynamics; lack of affirmations regarding cultural identities; and superficial exploration of cultural nuances in the supervisor dyad. Findings suggest supervisees need authentic, validating, process oriented exchanges in clinical supervision, especially in field internships where they are learning how to manage clients, their own lived experiences and authenticity in supervision. Recommendations for initiating transformative supervisory practices are included.