The ability to engage imaginatively with the lives of others is an important skill underlying the practice of both intercultural philosophy and interreligious dialogue. It can allow us to gain a sharper understanding of what people within different philosophical or religious cultures believe and value, of how their beliefs and values inform their life choices, and of what it feels like to live a life shaped by these beliefs and values. Imaginative engagement with others’ lives has been encouraged by several religious traditions, both Western and Asian. For example, the Spiritual Exercises developed in the sixteenth-century by the founder of the Jesuits, Ignatius of Loyola, deploy a constructive use of the imagination, as do certain Buddhist meditation techniques. Such uses of the imagination can, however, easily lead us astray. The more active our imagination, the more we might be led to form an impression of the lives of others that contains more fantasy than reality. If we are to harness the potential benefits of imaginative engagement with the lives of others, a structured method is required that can allow for deep exploration of others’s beliefs, values, commitments and motivations while minimizing the risk of arriving at an ‘understanding’ of these containing more fantasy than fact. This article explores one such method, ‘Exemplar Reasoning’, which focuses the imagination on the lives of figures who are regarded as exemplary within their own traditions.