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This study explored 26 Elementary Mathematics Specialists’ (EMSs) leadership, particularly strategies used to negotiate access to opportunities and influential interpersonal forces. The EMSs were boundary crossers leading from their classrooms with a primary responsibility of teaching students. Data were collected at the end of 5-year professional development through individual and focus group interviews. Utilizing and extending a framework of strategies, the analysis revealed structural and relational as prevalent, meaning existing school structures provided an entry point for leadership and building trusting relationships was key to accessing teachers. Interpersonal forces elevated and limited their leadership opportunities, including those related to formal school leaders. Findings illuminate how EMSs as teacher leaders seek to effect change within the challenges of non-distributed leadership systems.