In this paper, we critically interrogate the way in which comparative and international education coursework at two large institutions in Australia and New Zealand embody or challenge teleological, colonial, and Western/Northern-centric perspectives on education and development. Embedded within a broader and introspective examination of our roles as comparative and international educators in these universities, we deconstruct the intent behind our course objectives, readings, lecture content and assessment tasks, and place them into conversation with our own pedagogical self-reflections, observations of practice and student feedback. In doing so, we highlight ways in which we believe we are beginning to prepare a new generation of more critically conscious, and regionally-minded set of teachers, development practitioners and researchers. Specifically, by "making the familiar strange," and encouraging our students to co-construct knowledge, we argue we can begin to create actionable spaces which encourage an alternative reading of the world; something colleagues from across Oceania and further afield have long argued for as part of the decolonizing process. We also highlight how this process has led us to better recognize our own positionalities and epistemologies as CIE educators, in hopes that it can lead to an ongoing space for dialogue between educators and researchers within and beyond the region.