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The stress of myriad educational challenges has led to a marked increase in principal turnover in recent decades (Snodgrass Rangel, 2018) necessitating an understanding of the impact changes in leadership can have on a school’s ability to meet new challenges. This paper considers the experiences of three schools as a single principal transitioned among the school sites over seven years. Drawing on complexity thinking (Davis & Sumara, 2006; Lichtenstein & Plowman, 2009), this study explores the extent to which the principal impacted each school’s readiness for change through interconnected processes of distributing authority, creating a common vision, and fostering relational trust—with a focus on how one may navigate the initial conditions they came to face but could not control.