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Within a two-year principal preparation program, the role of field supervisors was replaced with a coaching model with coaches not serving in an evaluative capacity. This case study of the entire principal coaching staff consisted of individual interviewers of former. The purpose of this study was to examine their efforts to mentor toward the program’s goal of leading with anti-racist and equity driven perspective. We found that while the coaches were grateful for the trust the program placed in them and their comfort with coaching strategies, many expressed and desire for more guidance about advocating for equity and antiracism. Previous expertise as school leaders was not always matched by sufficient understandings and confidence with navigating equity concerns.