This article describes the perceived barriers to building learning communities, and the impact of self-assessment on two cases. One, a graduate cohort used traditional summative methods, employing Senge’s (1990) characteristics as the self-assessment dimensions. The second, a following cohort, was introduced to dynamic self-assessment early in the program, using the same criteria. Interview data was collected. Barriers to building communities were elaborated, including individual, structural, and systemic processes. Differences were noted concerning community formation, and how participants lived the community experience. The cohort using dynamic self-assessment displayed more systems thinking, an elaborated shared vision and conceptualization of team learning; a deeper questioning of mental models; and more personal mastery attributed to being a member of a learning community.