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The purpose of the present study was to revisit data collected and analyzed for four, U.S.-based empirical studies on educational leader professional development (PD). These studies examined teacher leadership, school improvement, and educational leaders’ implementation of new evaluation systems. Using abductive analysis, we used an analytic frame based on transformational learning, pillar practices for adult learning, and powerful learning experiences (PLEs) for educational leaders to examine PD participants' experiences and what enabled and hindered high-quality experiences. Findings suggest a number of benefits, such as role-specific PD, and barriers, such as one-shot offerings. Implications suggest that creating conditions for transformational learning is possible when using pillar practices and PLEs.