This article reports findings from a research program exploring the role of mediation in an "adaptive learning" process through study of developmental evaluation (DE). Our study focuses on how mediators might influence the relationships between components of a social learning system and the implications for adaptive learning. Specifically, we focused on evaluators making space for the interrogation of ideas and choices, why this is important, what strategies are used, and what challenges present. Data from a multiple case study of four DEs revealed multiple drivers behind a need to make space, including new trust factors, uncertainty and anxiety, and learning-related norms. Strategies that were employed included turning down the heat, seeking balance among competing needs, normalizing evaluation practice, and legitimizing DE. Results are discussed in terms of implications for evaluation capacity building in adaptive learning contexts. Questions for future inquiry are posed.