When exploring leadership theories, models, and practices, it is difficult to ascertain if there are approaches that are better suited to cultural organizations. This chapter examines the adaptive leadership model developed by Heifetz, Grashow, and Linsky, the attributes of adaptive organizations, and will consider if this leadership model could help cultural organizations thrive and be more resilient over the long run. The unique leader and follower component of adaptive leadership will be explored using examples related to arts and cultural organizations. Limitations of the model will be discussed including its complexity and the demands placed on the individual attempting to lead adaptively.