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Navigating tensions raised by competing demands, increasing socio-political forces, and persistent dwindling of state education funding has made the school superintendency, even in its best days, a highly challenging job. While larger-sized, well resourced school districts may have more room in their infrastructures to help shield and navigate such challenges; rural and small school districts are often too confined to proactively reduce the negative impacts potentially induced by such challenges. Moreso, there is limited knowledge about superintendency in such small rural districts, not to mention how these district leaders creatively navigate tensions during times that are disrupting, for instance, during a global pandemic. A case study is presented highlighting one small rural school district superintendent’s experience in leading through such circumstances noted above. Particularly, with an influx of a significant amount of grant money right before the pandemic and the expected delivery of certain outcomes highlight an intensification of the feasibility-versus-sustainability debate. Using adaptive leadership as the theoretical lens, the case’s real-life scenarios and ensuing analyses of them underscore the complexity presented to the superintendent related to school finance and organizational relationships that can benefit educational leadership educators and practitioners.

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