Communicative evaluation is a type of community-engaged scholarship that encourages collaboration between stakeholders and evaluators as they develop an action plan about a social problem. However, extant research has failed to adequately explore issues of power and identity encountered by communication evaluators in the field. Doing so could enrich assessment processes and outcomes to develop more nuanced theory and practice. Thus, we reflexively develop and integrate our personal stories and experiences of conducting communication evaluation research to highlight four dialectic identity tensions: (a) insider/outsider; (b) expert/novice; (c) program sustainer/impeder; and (d) researcher/friend. By displaying these tensions, we reveal potential opportunities for new insights that could offer pragmatic applications more attuned to the people and contexts of evaluation research. These tensions highlight the need for critical reflection in the pursuit of program sustainability and offer points for transformation. We conclude with pragmatic recommendations for engaging reflexivity in communication evaluation research.