This article describes a process of live supervision that has been designed to encourage trainees to experience competing theoretical perspectives. It involves the use of separate T (treatment) and O (observation) teams who conceptualise the same case from two broadly defined theoretical perspectives, variously called first and second order, modern and postmodern, or family systems and social constructionist. The process requires trainees to adopt multiple positions rather than identify with one perspective, and provides a basis for comparing and potentially integrating them. We provide examples of the approach, discuss important contextual issues for supervisors to consider when implementing it, and examine ways of adapting it to a wide range of training contexts.