This article discusses the training of art mediators for documenta fifteen, and how this affected the mediation team during the exhibition. The question of what conditions collective art mediation needs to succeed is considered from a critical perspective, analyzed along the lines of three aspects: foundations, framing, and methods. It shows that collective work requires common ground, both on the social level and in terms of substance. In particular, it argues that a consistent position toward mediation at documenta fifteen requires the integration of critical pedagogy. Beyond this, it also discusses the processes that arose from the group’s framing, both as a collective and as friends working within an institutional framework and social structure. It also questions whether methods of art mediation are relevant in a documenta oriented toward postcoloniality, offering an insight into strategies and methods of critical art mediation.