In this reflective essay, we seek to stimulate new debate on the social purpose of place leadership. We begin by considering the meaning and relevance of purpose in the formal leadership endeavour, and the likely nature of social purpose in place leadership in the face of multiple meanings. We use this discussion as a basis for exploring what a more emancipatory leadership stance might comprise and pose four awkward questions concerning our imagining of what an emancipatory-oriented place leadership might look like in practice. Insights are drawn from a range of interdisciplinary literatures, including critical leadership, organizational studies, management learning and sub-national development. In keeping with the need for greater critical reflection, we seek to combine broad theoretical insights with our own reflections on the practice(s) and action(s) of place leadership, from our ongoing empirical observations of leaders in our own research, and our prior professional experiences as economic, regional and community development practitioners.