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This article reports findings from evaluation research conducted from three conferences in the Authority, Power, and Justice: Leadership for Change series, convened annually from 2014 to 2016 at Boston College. The conferences have had similar structures and themes, with some slight variations. The highly diversified staff and membership has highlighted the themes of social identity, power, and justice in the conferences. Findings were consistent with prior research that participants do indeed learn at conferences. For both experienced and inexperienced conference members, the process of learning and meaning making is complex, relational, and evolves over time beyond the conference boundaries, and is idiosyncratic and variable. Learning can also occur at a steep cost. Recommendations are offered for enhancing learning and mitigating some of the factors that may interfere with learning. Suggestions involve re-thinking our notions of conference boundaries and the consulting stance, better integration of conference themes into conference structure, and integration of evaluation processes into conferences.