This article describes the results of a pilot project on using historical reflection as a tool for policy-making in the humanitarian sector. It begins by establishing the rationale for integrating reflection into humanitarian practice. It then looks at the growing interest in humanitarian history among practitioners and academics over the past decade and sets out the arguments for why a more formalised discussion about humanitarianism’s past could result in a better understanding of the contemporary aid environment. The main body of the article focuses on our efforts to translate that potential into practice, through a reflective workshop on Somalia since the 1990s, held at National University of Ireland, Galway, in June 2017. Drawing on our experience of that event, the article puts forward four principles on which a workable model of reflective practice might be developed: the importance of the workshop setting, how to organise the reflective process, the value of pursuing a single case study and the careful management of expectations and outcomes. This article is not intended to be prescriptive, however. Rather, our aim is to put forward some practical suggestions and to open a conversation about how a model of historical reflection for aid practitioners might be developed.