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This paper makes a methodological case for studying organizational leadership in public alternative schools, specifically those meant for problematized and educationally displaced young people. I begin the paper by reviewing scholarship on models of transformative leadership, structuration and enclosure, and alternative schools, demonstrating the need for empirical research that makes visible the intersections of agency and structure in transformative leadership efforts in schools. I then draw on the example of continuation high schools to provide conceptual framing of the distinctive spatialities of alternative schools which create spaces of possibility that illuminate leadership agency. I finish by suggesting that studying organizational leadership in alternative schools provides a window into how enclosing organizational structures in schools are made, evolved, sustained, and transformed.