In this chapter, we draw from the literature on positive organizational scholarship to inform and extend current theories and research on leadership development in organizational settings. Specifically, we highlight the value of a strengths-based approach to leadership development, draw attention to the emergence of positive cycles of leadership development, and emphasize the role of high-quality relationships and connections in facilitating leadership development. Our hope is that these theoretical insights provide the basis for new theory on cultivating extraordinary leadership capacity in organizations and stimulate future research on the positive and dynamic processes involved in leadership development.