Norms of Whiteness are pervasive throughout schooling in the United States (Tanner, 2017). Critical Whiteness studies (Kincheloe, 1998) and second-wave White teacher identity studies (Jupp & Lensmire, 2016) provides relevant insight into the thoughts and experiences of White preservice and in-service teachers. This paper draws on the literature to explain the author's varied personal experiences with Whiteness in education. It is the author's hope that the experiences shared will resonate with readers and complicate racialized experiences in education, as well as provide a springboard for supervisors to develop White teachers' capacity to create anti-racist, democratic classrooms. Keeping in mind the goal of supervision -- improved learning for all students through the development of teachers -- this paper puts forth the argument that in order for teacher supervisors to do such, supervisors should explicitly name Whiteness and facilitate conversations or open spaces for dialogue on the problematic nature of Whiteness in schooling.