Evaluations justify resource allocations and shape future actions. In settings working to improve health and economic mobility, this is a high-stakes activity. Program evaluations often focus on the topic at hand, leaving the issue of race and race relations (historical and present) out as the work of diversity, equity, and inclusion efforts and not central to program implementation. However, many of the programs we are hired to evaluate involve populations living out the legacy impacts of structural racism and discrimination. This article acknowledges different forms of resistance experienced when integrating questions about racism into evaluations. It draws on my experience in a collaborative process of creating a guide intended to be used with stakeholders. I present challenges that others setting out to include structural racism and discrimination into processes of evaluation may encounter and highlight how the qualitative interview process is itself an intervention in facilitating reflection and action.