Effectively supporting adult development on the front lines of schools is no easy task. In this article, the authors report on talks with education leaders about the most pressing challenges they face in supporting adult development in their schools and organizations. The leaders participated in a graduate course about supporting adult development as part of their leadership training and shared how they use developmental principles and practices in their work and the obstacles they encountered along the way. Three of the most common obstacles the leaders cited were: understanding and managing resistance; finding time to support teachers' professional learning; and finding forums to grow as leaders. Using strategies that addressed overcoming these three common obstacles helped the leaders see developmental desires as an enduring core of effective leadership, rather than a simple add-on or supplement. Eager to implement developmental ideas in their own contexts these leaders learned that supporting adult development is neither simple nor straightforward, but a process of building and sustaining growth-oriented cultures over time, adaptation, responsiveness, and imagination in order to challenge resistance, build time, and create the conditions for everyone to grow.