This paper focuses on the phenomenon of middle leadership as experienced in a university context and specifically, 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), the paper critically examines how middle leaders learn or come to know aspects of their role, and the learning opportunities and challenges associated with their middle leadership position. 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. As middle leaders, learning involves those above us (our leaders/line managers), those alongside us (our colleagues/middle leaders of other departments), and those below us (those whom we lead/line manage). The paper arises from a research project that has facilitated professional learning conversations between the three authors and supported us in adopting a relational perspective in our exploration of our experiences as middle leaders. This perspective has allowed us to examine the learning constraints and affordances arising as a result of others above us organising events, creating practices and constructing artefacts for us. It has helped us to consider how we can work collectively with our colleagues to renegotiate events, practices and artefacts; and it has suggested ways in which we can create better learning opportunities for those we lead. Finally, it has led us to identify ways in which the learning opportunities for middle leaders may be enhanced within the university sector.