This case study draws on insights from my PhD thesis, which was the first comprehensive study of the professionalisation of psychological counselling in post-socialist Russia. The study aimed to understand the process of professionalisation and reasons for the feminisation of this profession. This research drew on 26 in-depth, semi-structured interviews with practising counselling psychologists, and fieldwork was carried out in two Russian cities, Moscow and Vladivostok. In this case study, I explain some issues in the process of cross-cultural interviewing, focusing specifically on the issues of researcher positionality and the insider/outsider dilemma. I discuss how my insider/outsider position shaped the interview process and explore ways of dealing with it methodologically.