In this reflective case, we examine the role and function of collaboration in use-oriented evaluation approaches. Reflecting on our experience evaluating a program that sought to integrate new technologies into K-12 teaching and pre-service teacher education, we found that the desire and pursuit of making evaluation useful can influence why, with whom, and how we choose to collaborate, in turn shaping the substance of our evaluative questions, methods, and findings. We structured our reflections using the Describe, Analyze, Theorize, Act model (Peters, 1991; Smith et al., 2015), a tool for systematically reflecting on evaluation situations and dilemmas to learn and refine future actions. Through this process, we uncovered both conceptual and practical implications regarding the relationship between use-oriented evaluation approaches and collaboration.