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The field of educational leadership presents us with a pressing challenge and opportunity. Spurred by new research, the school leadership literature has clearly identified a consensus that leadership capacity matters for school improvement. However, little is known about the most effective ways to develop leadership capacity in either individuals or in schools, or the processes by which this learning unfolds. Thus, we have a clear need but little guidance on how to best invest resources to develop the strongest cadre of high quality leaders to meet the growing need in our schools. This research explores this “black box” of leadership learning, using grounded theory and phenomenological approaches to generate new knowledge of the whys and hows of individual leader development.