The Royal Canadian Army Cadet League is a national organization promoting community youth leadership skill development through an afterschool program format called "corps" across communities in Canada. Each corps is attached to a Canadian Forces Reserve Regiment. However, numerous corps are experiencing a decline in retaining their youth members. This decline in retention jeopardizes each corps’ funding from the Department of Defense, possibly closing the community corps. Examining retention through the lens of critical pragmatism will identify areas for improvement. A paradigm shift from primarily transactional-based leadership to transformational and servant leadership is required to improve the organization, ensure sustainability in the corps, and support the Canadian Armed Forces. Using mixed and current best practices for engaging youth and inserting a more applicable framework for teaching and training with a transformative change in mindset for the corps leadership, will improve the organization and ensure sustainability with a model of inclusivity. A leadership framework supported by recognized change path models with reinforcement from continual monitoring and evaluation will ensure a continued corps presence in the community.