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Our project explores how teachers undertook critical and dialogic conversations necessary to advocate for multilingual learners through roleplays. Using Critical Dialogic Education, researchers analyzed data from a graduate-level online ESL teaching methods course where participants engaged in synchronous roleplay assignments between ESL teachers and administrators. Our inductive/deductive analysis finds how teachers used varied tactics to challenge administrators' views while negotiating power dynamics: noticing inequities as structural and persistent; recognizing that challenging the status quo required knowledge of systems and empathy with leaders and students; taking action through relationship-building and suggesting concrete next steps. This work demonstrates how teachers collaboratively deepened understanding of advocacy through structured roleplays, engaging in critically oriented and self-reflexive practices essential for supporting multilingual learners.