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Many teacher education activities present “best practices” for teachers while overlooking complex dilemmas that arise from conflicting pedagogical commitments. This comparative case study explores how two experienced secondary mathematics teachers involved in a video-based formative feedback (VFF) cycle navigate and make sense of pedagogical dilemmas. By analyzing data from two VFF sessions, the study reveals how teachers leverage aspects of these dilemmatic spaces to explore and make sense of dilemmas. Teachers may benefit from the visualization and collaborative discussion of their practices, which allow structural and relational elements of dilemmas to surface. This research contributes to a deeper understanding of teachers’ dilemmatic sensemaking and how professional development can support teachers in managing complex dilemmas without prescribing universal solutions.