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Contemporary educator preparation programs face legislative constraints that limit critical discussions of systemic inequities, leaving future educators underprepared to support multilingual community thriving. We explored how video-mediated transcultural dialogues between 90 U.S. and Taiwanese pre-service educators fostered essential critical cultural competencies. Using a critical global literacies perspective, we analyzed participants’ discussions of unfamiliar educational practices. Analysis revealed participants developed interconnected global awareness, self-determination, reflexive relationality, and social justice orientations through modest individual perspective shifts that created a foundational framework for broader educational transformation. Despite limitations including small sample size and two-terms duration that narrowed generalizability, this pedagogical innovation demonstrates a viable pathway for developing critically socio-politically conscious educators within restrictive contexts while building lasting transcultural partnerships.