This chapter explores the application of adaptive leadership principles to the challenges of transitioning towards circular economies. As organizations and societies grapple with the complex task of shifting from linear to circular economic models, there is a growing need for leadership approaches that can navigate the adaptive challenges inherent in this transformation. The chapter examines how key concepts from adaptive leadership theory, such as distinguishing between technical and adaptive challenges, mobilizing collective action, and managing systemic change, can be effectively applied in circular economy contexts. It discusses the theoretical implications of this intersection, including the need for more systemic, process-oriented, and distributed understandings of leadership. The chapter also outlines practical implications for leaders, emphasizing the importance of developing enhanced diagnostic skills, creating effective “holding environments” for stakeholder engagement, and fostering cultures of experimentation and learning. Finally, it proposes avenues for further research to deepen our understanding of effective leadership in sustainability transitions. By bridging adaptive leadership theory and circular economy practice, this chapter contributes to both leadership studies and sustainability management, offering insights into how leaders can more effectively drive the transition towards more sustainable and regenerative economic models.