This analytical article largely draws on the experiences of visiting faculty teaching at post-secondary institutions overseas. What is largely understood in the literature is that visiting faculty need to navigate the sociocultural, professional, and contextual differences that shape the work context. Drawing on the theory of border pedagogy, this article takes the scholarship further by proposing and elaborating on a pedagogy of preparedness that may help to facilitate visiting faculty acculturation and analyze dominant and marginal narratives in the new work situation. This pedagogy is based on (a) pre-departure learning, (b) deconstruction of transnational teacher and teaching background, and (c) decolonizing learning spaces.