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In an examination of the factors shaping transformative leadership, this mixed methods study explores the influence of educational and professional experiences on an individual’s transformative leadership orientation. Through hierarchical regression analysis, this research quantified the impact of degree attainment, leadership roles, and leadership experience on transformative leadership scores. Findings also revealed people of color received higher scores than those who identified as White, and faculty and staff received higher scores than administrators. Preliminary qualitative data describe how experiences of attaining an advanced degree develop transformative leadership skills.