Our understanding of leaders and the role they play in organizations and society is changing, which has important implications for leadership education. At the turn of the century, society began to move from a mechanistic understanding of leadership to a more ecological one. The latter, ecological approach to leadership is characterized by collective decision-making, collaboration, shared leadership, and grassroots organization. While leadership educators have acknowledged this shift, more case examples are needed to illuminate practical implications for leadership. This study of county 4-H associations uses an explanatory sequential mixed methods design to explore the relationship between three factors: (a) subjects’ levels of hierarchical and systemic thinking; (b) how their associations engage in leadership and organizational learning; and (c) programmatic success. While no direct relationship emerged between programmatic success and subjects’ levels of hierarchical and systemic thinking, mixed methods results revealed several distinctions between high and low scoring programs’ approaches to leadership. These distinctions support an ecological approach to leadership, which in turn impacts modern approaches to leadership education.