Leaning on Greenfield’s seminal work, we argue that deliberations in ‘educational administration’ should capture the experience of ‘doing’ leadership as a practical activity in a complex organisation (Eacott, 2010); a need amplified further in the particular area of leadership development. Accordingly, we advocate an appropriate blend of theory, research and practice. First, we examine theories of organisation informing our understanding of schools as complex, social worlds and the practice of leadership that seems to be required in such environments. Specifically, we adopt three separate but interrelated lenses that have sharpened our understandings of organisational complexity – social constructivism, micro-political theory and complexity theory. We then discuss connections between these foundational beliefs and the methodology we adopt for investigating principals' work and ascertaining the efficacy of leadership development processes. Our paper concludes, therefore, by articulating a heuristic framework for principals’ learning derived from rich and realistic portrayals of their everyday work created by our research. The framework is fundamentally descriptive rather than integral to a normative theory or model. We believe that if school leadership is first described accurately as it is, there can be agreement on changes that will create things as they ought to be.