This paper describes the use of cohort structures in management and leadership education. Cohorts privilege social interaction as the locale where cognition and culture are co-created between individuals. A cohort learning community format allows students and faculty to create opportunities for significant and deep learning—learning that integrates both the conceptual, the social and emotional, the self and the other—in relational spaces by promoting zones of proximal development, multisubjectivity, multivocality, and shared cognition. These are hallmarks of effective learning organizations and communities of practice. But they also present significant and tough challenges. Using creative nonfiction to frame reflections, five authors illuminate their experiences in cohort communities: the benefits, difficult sides, and challenges of creating crucible spaces where social and emotional learning can be explored, and its role in promoting transformational learning.