All social and professional practices are historically situated, evolving forms of acting and interacting. Evaluation, as a practice, is shaped by and shapes the practice evaluated. This article contributes to responsive and values-engaged evaluation approaches by reflecting on the space where these two practices intersect. The evaluative task was to document the nature of a partnership between a university and school district and how that partnership was being carried out in the form of a professional development school. The authors focus on the role that participant observation, as an interactive and responsive form of engagement, played in the evaluation. Through two lenses—observing the partners and observing ourselves—the authors critically reflect on their decision-making processes, assessing their accomplishments and shortcomings. The authors conclude by considering how they might further their engagement as values-engaged evaluators in this context in ways that support the development of both the evaluators and the evaluand.