This article focuses on the phenomenon of middle leadership in a university context and directs attention to the significance of learning as a central facet of leadership development. Drawing on the reflections of two of the authors as new middle leaders (chairpersons of departments), this article critically examines how middle leaders learn aspects of their role. Two tenets underpin our analysis: learning is fundamentally a social process - we learn with and from others; and learning is relational - what and how we learn is determined to some extent by others and affects others. Our experiences point to learning constraints and affordances arising from events, practices and artefacts. Constraints were largely associated with transmission learning experiences, while affordances were found in collaborative knowledge-sharing contexts that arose as information grounds in response to an information need. We argue that both those we lead, and the organisation itself, would likewise benefit from a knowledge-sharing perspective on learning.