In Taiwan, there are service learning programs organized by older adult educational institutions that are held in high esteem. Director leadership plays a key role in the effectiveness of such institutions, and the leadership experiences of such directors in guiding service learning are worth exploring. This study conducted a qualitative approach and selected directors from eight Active Aging Learning Centers (AALCs) who achieved outstanding leadership effectiveness to take part in one-on-one and in-depth semi-structured interviews. The results indicated that: 1. Directors infused the entire service learning process with inspirational motivation by adopting through individualized consideration as a starting point. 2. When directors led the preparation process for service learning, they focused on inducing intellectual stimulation among the older adult learners, such that they felt empowered and capable of providing community services. 3. During the community service phase, directors practiced a form of leadership characterized by idealized influence to encourage, accompany, and support the elderly while they engaged in service learning. 4. The dilemma faced by directors was dissatisfaction with the leadership. Directors responded by reminding them of their original service learning intention and downplaying issues, which made the service learning group undergo a positive transformation. 5. The results of directors' leadership had a positive effect on the community as it led to more dynamism and more people participating in community service.