This article addresses some of the challenges faced by researchers who are seeking to identify, gain access to, conduct interviews with, and analyze data from elites. Drawing on the first author's experience of conducting elite interviews as a source of social research regarding laws and legal processes, this article offers both theoretical and practical insights. Theoretically, we examine interviews with senior legal experts as a particular form of elite interviewing. Interviewing legal elites poses its own set of challenges that at times relate to and sometimes depart from other experiences of interviewing elite groups. Practically, we provide suggestions for how researchers new to elite interviewing and those more experienced can reflect on and navigate different stages of their field research to help capture novel insights. Paradoxically, we show that while an uncomfortable conversation can appear to the researcher that it has not gone well, often it can be a sign of a high quality elite interview.