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This chapter explores the relevance of critical race theory (CRT) and queer theory to the relational aspects of program evaluation. Often conceptual binaries that undergird traditional evaluation theory and practice (e.g., internal versus external evaluation, subjective versus objective analysis, observation versus intervention, and insider versus outsider positionalities) adversely influence rigid social roles between evaluator and participant limit a study's effectiveness in supporting programs for equity in contemporary school districts. To illustrate this approach, an array of problems within a program evaluation of a district-wide ethnic studies reform initiative is presented. Approaches to these challenges rooted in tenets of CRT and queer theory illustrate how the district was able to clarify goals and develop an effective implementation plan that focused on effective ethnic studies curriculum and pedagogy.