Challenging and confronting educational systems and structures, the vast majority of which come from a place of privilege, is uncomfortable but necessary. Education, from early childhood to post-secondary, should challenge and address the racial inequities that inevitably characterize such systems and structures. Yet, we do not always do this explicitly, for a number of reasons. First, this is hard work, and educators must deal with many pressing needs on a day-to-day basis, so difficult conversations about racial inequities are pushed to the sidelines. Second, many educators do not have the training or resources available to collect, access, or analyze their data with a critical lens around racial equity. Third, many educators are White, and therefore have not personally experienced what it means to navigate interactions that are based upon racial biases or systems of structural racism. Without this firsthand knowledge, they may not be aware of the impact on youth outcomes--from disengagement to academic challenges--and the critical need to address these systemic issues. Even educators of color, within a system that privileges Whiteness, can struggle with internalized oppression or the same lack of tools and training as White teachers. The authors of this article, a school district superintendent and a university professor in Rochester, New York, are an example of how educators can collaborate around diversity and racial equity. They present a framework for grounding difficult conversations on race and implicit bias in system-level data, to avoid blaming and shaming and to break through defensiveness to arrive at solutions.