Huddles—informal gatherings of two or more individuals, convened to discuss substantive issues regarding the work of one or more of the participants—are a form of social interaction that can play a critical role in the learning of organizational actors. We identify their defining properties and propose a multi-level framework for understanding the participant- and huddle-level factors that promote individual learning that is important to the work of the organization. We test our hypotheses using data obtained from huddles conducted in newspaper newsrooms using an experience sampling approach. Results confirm the importance of occupational tenure heterogeneity, perceived job relevance, attention to others’ emotions, and conversational reflexivity for participant learning in huddles. These results set the stage for understanding how the informal structure of an organization can be developed in ways that promote learning and adaptation.