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Teacher retention has been a continuous challenge in the U.S. This study presents an investigation of factors that relate to retention and a comparison between Master Teachers (MTs) and non-MTs. Eighty-five MTs and 82 non-MTs were compared in terms of their self-efficacy, leadership engagement, school-work environment, diversity dispositions, and professional network characteristics. Moreover, we investigated how these factors related to their retention using multinomial logistic regression. Results indicate that MTs: (1) have higher levels of self-efficacy and favorable network characteristics; and (2) are more likely to shift to leadership positions. Findings provide support for teacher leadership programs in promoting leadership roles for teachers. Lastly, the findings suggest that school administrators have a responsibility to engage teachers in leadership activities.