This chapter describes evaluator behaviors revealed by the case analysis of a participatory and developmental evaluation. The analysis revealed that the evaluator paid specific attention to individual stakeholder cues. These cues were related to three elements of the evaluation: negotiating the design, monitoring individual stakeholder needs, and interpreting the evaluation findings. Rather than occurring with the stakeholders as a group, these elements featured the evaluator working with individual stakeholders to establish trust, foster collaborations, and promote learning. This view of the evaluation process as a non-linear progression of engagement between evaluator and individual stakeholders challenged the study's initial phase framework. Distinct aspects of the methodology including a reflective journal that documented the evaluator's decision-making process and critical episodes created a way to understand the circumstances surrounding shifts in the evaluator's behavior. The conclusion describes implications for evaluation practice including the influence of developing close engagement with stakeholders, incorporating an evaluator reflective journal, and integrating evaluator past experiences and new theoretical frameworks.