This study aimed to identify the “ladders for leaders in irrigation pond management organizations” and to provide recommendations for developing the next generation of leaders through this process and via the role of their supporting organizations. Specifically, the study examined what knowledge and behaviors were important to leaders and how they acquired them. In this study, interviews were conducted with leaders in the Higashi-Harima region of Hyogo Prefecture. The results revealed that current leaders prioritize interpersonal coordination and organizational management skills over irrigation pond management techniques. Furthermore, these skills are largely derived from their experiences outside the region. This indicates that farmers with little local experience can become potential leaders if an appropriate ladder is established. This presupposes a small but significant regional experience; to maintain these ladders, it is necessary to create and strengthen intermittent opportunities for knowledge sharing within the region.