Leadership transition literature indicated that nonprofit sector current leaders lack understanding of proper ways to make use of relevant management leadership techniques to develop new leaders. New leaders replacing retiring organizational leaders lacked managerial experience and training needed to lead employees and manage organizational resources. The purpose of this study was to explore, understand, and interpret leadership supportive systems techniques that characterize "Plan A," vision used for professional development of aspiring nonprofit executives for capacity building of critical leadership skills and management of networking functions toward organizational sustainability. The conceptual framework of this study focused on supportive systems leadership development theory, nontraditional leadership development theory, and "Plan A" leadership development theory. The study adopted qualitative exploratory-interpretive case study to generate research data through surveys, document analyses, interviews, and focus group discussions for research questions 1 and 2. Data generated were analyzed using embedded thematic data analysis strategy and qualitative NVivo 11 software. The major integrated themes that emerged characterizing the unique features of "Plan A" vision of nontraditional leadership development techniques were: (a) vision and leadership empowerment, (b) performance and feedback, (c) efficiency and conflict management, and (d) effective communication between leaders and aspiring executives in the workplace. The study contributed to nonprofit leadership transition by interpreting and providing in-depth understanding of leadership development roles that involved leadership development persuasion, collaboration, consultation, and encouragement for aspiring executives to seek leadership roles within the nonprofit management team.