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This self-study traces Sharon’s transition into a deanship, revealing how teacher education leaders navigate resistance and opportunity while pursuing reform. Guided by Berry’s (2007) tensions of telling and growth and planning and being responsive, we analyzed narratives created through nomadic writing and critical friendship. Thematic, process, and focused coding produced two findings: (1) change required working through others rather than directing them, and (2) leading reform demanded continual recalibration between long-range plans and emergent contexts. Trustworthiness was supported through contextual detail and transparency. Results underscore leadership as on-the-job learning, complicating images of administration and highlighting identity work, distributed influence, and strategic responsiveness. Implications address preparation and support for teacher education leaders committed to sustained, equity-minded program improvement and ongoing efforts.