National attention to a possible superintendent shortage has created concern about the changing nature of the superintendency, particularly new challenges, and how superintendents are prepared. Through 23 focus group interviews, superintendents across the country described the challenges they faced when new, how these have changed in recent years, and the benefits and gaps of their leadership preparation. Through a grounded theory analysis and comparison with relevant adult learning and leadership development theories, this article argues that structured advanced leadership development experiences could improve superintendents' leadership development and transition. The article recommends that these experiences be structured as a learning community that is experiential and intensively reflective.