The National Coaching Certification Program is an adult education program in Canada that provides education to individuals engaging in sport coaching. In this program, certification is achieved through a successful evaluation. This research examines the perceptions of master coach developers, leaders of coach education in Canada, specifically exploring what factors contribute to them feeling confident and competent in leading National Coaching Certification Program evaluations. Ten master coach developers from across Canada were interviewed, and the following themes were identified: opportunity to engage, connection with participants, and perceptions of evaluation tools and processes. Constructivist grounded theory guided the research, supporting the development of the theory of evaluation leadership in the National Coaching Certification Program. This theory describes the impact of focusing on relationship, process, preparation, and practice on the perceived competence and confidence of program leaders in adult learning.