This article argues that little is known in public relations (PR) about the experience of leadership and, more specifically, the challenges associated with enacting desired leadership behaviours in the work place. The study focusses on the personal experiences of PR leaders and considers how exploring the interplay between a leader and their context enhances understanding of the conditions under which knowledge is enacted, or rather not enacted, in different leadership situations. The discussion is informed by perspectives from organization and leadership studies which highlight the importance of reflexivity to leadership learning. In addition to applying a reflexive lens to leadership practice in public relations, the study addresses a lack of empirical research focussing on the situated experiences of PR leaders. It considers the reflexive potential of a programme of interviews with PR practitioners providing examples to illustrate the role this form of research can play in leadership studies. The context investigated concerns the work place experiences of senior PR executives who claim to be ‘empowering leaders’. The discussion of the findings focuses on how organizational power relations distort the practitioners’ espoused leadership values and engages in a process of problematization designed to challenge the uncritical promotion of normative and decontextualised approaches to leadership. The article highlights the benefits of a reflexive orientation to PR leadership research and pedagogy, while calling for the promotion of a particular form of contextual intelligence to help practitioners confront the organizational conditions which specifically impact on their ability to lead others.