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This study explored four teachers’ experiences with relationship building and sustaining. Positive teacher-student relationships are linked to higher academic achievement, increased engagement in learning, and are integral to a successful classroom experience. This qualitative, multiple case (aka multicase) study is grounded in Interpretive Phenomenological Analysis (IPA). Core to IPA is the belief that experiences can be interpreted and comprehended through various lenses and perspectives. Data collection for this qualitative case study was cyclical alternating between interviews, teacher self-reflections, and classroom artifacts. Findings elucidated characteristics of the teachers’ approaches to their relationships with students. Deeper knowledge about self, student cultures and experiences, and intentional relationship-building strategies were significant for building and sustaining relationships, adding nuance to other scholars’ explorations