Using judges and stage actors as instructive polar types this article elucidates factors that influence the inclination to empathise. Both come in close contact with dramatic life stories on an everyday basis but approach empathy from contrasting vantage points: emotional distance versus emotional engagement. Similarities between these polar types can thus disentangle some of the factors that influence professional empathic perspective taking in more general terms. It is argued that reality or fiction in itself does not promote empathy, but the presence of a complete narrative structure which allows for personal recognition of shared attributes or experiences. In both professions the decoupling of emotions from private connotations, individual responsibility for interpretations on stage or in verdicts and defamiliarisation of private experiences can promote empathic perspective taking whereas it is prevented by one-sided perspective taking; for example, by judicial encoding (judges) or getting stuck in private experiences (stage actors). Organisational obstacles to empathy include hierarchal work structures or a ‘teflon culture’.