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Following research on the challenges of transitioning from teacher education to teaching practice, this study examined the challenges and the experiences of early career teachers(ECTs) in Cyprus as they transition from academia to the classroom. Using a case study approach, we investigated multiple perspectives: prospective teachers, ECTs, and teacher educators. Data were collected through semi-structured individual interviews and a focus group interview. Data were analyzed comparatively using thematic analysis and open coding techniques to identify similarities and differences between the groups. Findings highlighted key challenges as well as elements for addressing the challenges of transitioning to classroom practice (e.g.,practical experience; teacher education focusing on the children; support needed during the first years of teaching; connection between theory and practice).