The purpose of this study was to understand the strategies leaders used to learn new roles during large-scale organizational change and to understand what organizations can do to support the learning process. This was accomplished by exploring the experience of 15 school principals who learned to lead in the midst of two complex organizational changes. The first change was moving from a centralized to a decentralized model of operating in a $15 billion organization. And second was the change in their role from Educational Leaders to CEOs. Data collection methods included pre-interview data forms, in-depth interviews (including critical incidents), and an assessment tool (Leadership Assessment Inventory). The data analysis resulted in a framework for understanding the competencies developed and the strategies employed by these leaders as they navigated new terrain and performed a new role. The elements identified within the analytical categories reflect both themes supported by selective literature and those that emerged from the participants. The findings confirmed that today's leaders develop new competencies and strategies to transition in a changing environment. The findings culminate in conclusions that respond to three core research questions. The first research question focused on the changing role of leaders during large-scale organizational transformation. The analysis yielded three components--a "Profile of the Emerging Leader" depicting critical competencies demonstrated in a changing organization. A more detailed analysis highlights those competencies experienced by principals as critical for "Driving and Sustaining Performance During Transition". A third finding emerged, which revealed "Emotional Intelligence Competencies" as leading areas of engagement for leaders driving organizational change. The second research question focused on strategies leaders used to learn their new role in a changing environment. Here, a new learning domain emerged referred to as "Learning through Emotion in Action" (Emotional Learning through Action); this learning domain, along with Experiential Learning and Collaborative Inquiry, provides a model of engagement that principals use to learn during transition. The third research question focused on how organizations support learning during change. The findings provided a model for an environment that supports leaders' learning during organizational transition. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]