This paper is structured around a dialogue between Hazel Wright, who is an experienced user and advocate of biographical teaching methods, and Paul Ashwin, who has some doubts about their benefits. A statement from Wright about the potential of biographical teaching methods is countered by Ashwin, who poses three challenges related to biographical teaching methods: the forms of biography that are legitimate; students’ relations to theory; and the impact of power relations. Wright responds to these by drawing on specific teaching—learning moments and the paper closes with an invitation to the reader to decide their position on the potential benefits and limitations of biographical teaching.