This article examines the cross-cultural complexities of teaching and learning processes at different levels in a family therapy training program delivered in a different country. It presents two interlinked narratives of an advanced family therapy training program delivered in Slovenia by a U.K-based family therapy training institute. The context in which the training was negotiated and planned is discussed, highlighting issues at the macrosystemic level. Dilemmas that arose in relation to differing beliefs about teaching and learning are elaborated. We examine power relationships, ways that we positioned ourselves and each other, and how we tried and sometimes failed to take these into account. We question how the issue of spoken language and its meanings creates its own constraints and power structures, and how we respond to the impossibilities of translation. We argue that it is through the examination of uncomfortable processes that we develop self-reflexivity and work toward more equitable relationships.