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This chapter examines the role that guided collaborative reflection can play in teachers’ development of decolonial thinking. Following research undertaken with teachers in England, Finland, and Sweden, this chapter uses data collected from preservice history teachers in England to investigate how HEADSUP resources can be applied in aid of encouraging preservice teachers to start to undertake the task of developing and interrogating their ways of knowing, to begin the process of decolonising their practices. Our research shows how HEADSUP can be applied to stimulate collaborative reflection among practitioners as a key starting point for the work of decolonising curricula and practices, in a bid to try and avoid issues of performative decolonisation.