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This paper is an investigation that tests a specific organizational improvement model (Author, 2012). Employing interviews and document analysis from six years of experience in two very different leadership preparation programs in different universities we are able to determine the flexibility and usefulness of the model. Using concepts that include organizational learning, sensemaking, and institutional isomorphism, we interpret candidates’ experiences creating and implementing organizational improvements. Preliminary findings indicate that candidates understand and apply the model appropriately. Implementation in internship settings is fraught with challenges that provide vivid learning experiences for candidates focused on common leadership challenges. Findings from this study inform research and practice in leadership preparation and regarding the professional development of in-service school and district leaders.