The purpose of this study was to determine the effects of participation in an educational leadership preparation program on the actual practice of school leaders and to identify how their experience in the preparation program supported their learning. Principals reported that their pre-service preparation influenced their leadership in ways that are associated with leader effectiveness but also indicated that the context played a role in determining how they activated their learning. The research on transfer and learning suggests that conceptual learning, abstraction, dissonance, and reflection play an important role; this study provides empirical evidence that each of these cognitive processes was a critical part of learning and contributed to long-term transfer. The pedagogical orientation of the program, and specifically the integration of concepts of constructivism and mastery orientation, supported the development of propositional and process knowledge. Perhaps equally important was metaprocess learning as individuals developed greater understanding of themselves, their ability to critically reflect, and a greater sense of self-efficacy, skills that contributed to continued learning after completion of the program. In terms of instructional strategies, reading was surprisingly important as a source of propositional knowledge but the data suggest that strategies that enabled the students to understand the ideas and situate them in the school environment contributed to metacognitive processing and were responsible for in-depth and lasting learning. The findings here also provide support for understanding transfer from a social constructivist perspective. This literature points to importance of identity and the study generates some evidence that learning is shaped by prior learning and experience, two areas that are relatively unexplored in the research.