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Situated within a collaborative study between teacher leadership scholars and local educational leaders, this paper presents a case study of one district’s efforts to reimagine leadership roles by expanding teacher leaders’ (TLs’) responsibilities to include both formal evaluations and instructional coaching. We examine educators’ experiences with this emergent form of shared leadership and the tension between support and accountability that it presents. Findings indicate that while educators support this district policy in theory, teachers’ actual experiences with TL support hinge on relationships with their TLs, school culture, and the constellation of TL responsibilities. With these findings in mind, the paper concludes with recommendations to maximize the potential benefits and minimize the risks of TL roles that include coaching and evaluation.