This article considers the problematic nature of primary headship. It reviews evidence of some of the most significant problems encountered by new and experienced heads derived from two sources: the UK dimension of a European questionnaire survey undertaken in the mid 1990s and more recent reports gained from interviews with serving school leaders. The article uses the evidence base afforded by these sources to identify a set of selected theory bases from which it constructs an original, pluralist conceptual framework, which it sets alongside a synthesized typology of organizational problems. It then presents its conceptual framework as a heuristic capable of clarifying the nature of school leadership and management problems faced by primary heads. Thereafter, it indicates how the model might be used to help heads analyze and address many of the problems they experience. The article draws on empirical data collected in the UK but argues that the conceptualization it offers is also relevant to school leaders in other national contexts. (Contains 4 tables and 1 figure.)