This paper proceeds from the basis that leadership can only be understood in context and by viewing it from the inside. In particular, it argues that the contextual complexity of small school leadership warrants attention from researchers, policy makers and system administrators and describes the nature of this complexity as depicted in the literature. It, then, reports a study being conducted in two states of Australia, which examines the ways novice principals of small schools located in rural and remote areas make sense of, and deal with, the contextual complexity of their work. Finally, the paper discusses the implications of the study for promoting understanding of small school leadership and for developing authentic means of professional learning.