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The role of professional development becomes an important tool for fostering cultural and social capital for educational leadership in formalized ways. Such outcomes associated with this process are used as transformational currency to recruit and retain school administrators and thereby foster a school context conducive to leading, teaching, and learning. Using the qualitative data from nineteen school administrators in an urban school district, this research analysis ascertains insight about how educational leaders understand the dynamics of professional development and its role for improving school outcomes through the dissemination of specific types of knowledge and training as well as mentoring structures. Such knowledge and training are transferable given the demands of educational leadership in urban contexts.