According to scholars and organizations that focus on the performance of organizations in the nonprofit sector, retaining loyal and engaged donors has been a critical component of sustainability. Through the conceptual lens of single- and double-loop learning and organizational communications theory, this single-case study explored donor communication strategies used by 3 executive-level leaders of a nonprofit organization in Minneapolis, Minnesota. Data collected from semistructured interviews, organizational documents, and Guidestar, an online information service specializing in reporting on U.S. nonprofit companies, were manually coded and thematically analyzed. Two key themes emerged: effective processes for donor communication strategy development and organizational learning strategy development. Strategy development may assist this Minneapolis company’s organizational leaders with improving retention of donors and participants in the company’s programs and services, increasing action plan completion rates, and integrating the lessons learned process during the development and implementation of communication strategies to increase donor retention. By bridging the gap between performance arts and social responsibility, this company’s leaders may engage both donors and participants, resulting in favorable retention rates. These findings have implications for positive social change. Nonprofit leaders’ models of effective communications strategies and processes to improve participant and donor engagement may ensure leaders’ ability to serve and improve their communities by engaging at-risk youth in programs designed to develop performance arts and leadership skills.