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. (Contains 1 table and 3 notes.)