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In an attempt to raise the level of leadership competence and to increase the number of qualified candidates for leadership positions within post-secondary institutions, many colleges are supporting leadership development training for faculty and staff. This qualitative case study explores whether participating in a leadership development program resulted in career advancements that can fill leadership gaps. The study's framework, expectancy theory, suggests that individuals who participate in leadership development expect to become leaders. This exploratory case study sought to learn whether, upon completion of a comprehensive leadership development program, participants applied for, and assumed, leadership positions. The leadership program under study was attended by a cohort of 58 participants from a diverse set of 17 institutions across Canada. A purposeful sample of 12 individuals was drawn from this cohort and participated in structured interviews conducted by the researcher. Data were collected and coded to reveal their career progression. The results provided evidence that using leadership development programs to fill a leadership gap is productive, and that the effectiveness of this strategy is enhanced when institutions purposefully select and support participants through all stages of their leadership development. Participants who pursued leadership opportunities indicated the importance of institutional involvement in leadership development. Social change can be achieved by following the recommendations of this study as they illuminate participant expectations, beliefs, and values that help create effective leaders who are more capable of providing better learning environments for students.