This scoping review of the international literature published over the last 50 years in educational leadership and management journals provides a thematic exploration of factors influencing pathways at the pre-entry stage of a principal’s career. Findings from a thematic analysis of 68 publications show that attention to prospective principals increased after the year 2000 and this was driven by four main concerns: underrepresentation of women and ethnic minorities, principal supply and demand, the principalship as a school improvement lever, and the expansion of leadership posts in schools. Selected articles addressed three dimensions of the pathways before a person is first appointed to this post: (a) micro (individual’s agency), (b) meso (preparation of prospective principals), and (c) macro (policies shaping access to the post). Across time and countries, pathways to the principalship are resourced by individuals’ professional orientations and by contextual factors, formal pre-service preparation may be desirable but not always available or required, and policies frame a conceptualisation of the principalship that shapes the two previous dimensions. The internationalization of research on pathways to the principalship has brought to the forefront normative assumptions that should be critically challenged when considering how to recruit, develop, and support prospective school principals.