Canadian policy related to colonialism has created substantial challenges for First Nations, Métis and Inuit (FNMI) youth and has had a negative influence on their health and well-being. Sport-for-development (SfD) programmes are beginning to show positive impacts for children and youth internationally. This approach may also be beneficial for FNMI youth in Canada. This research evaluates the implementation of a SfD programme designed to enhance leadership skills for FNMI youth. A qualitative approach that examines contextual and implementation issues was used. Data were collected using semi-structured interviews and analyzed using thematic analysis. Findings were organized into themes related to strategies for success and challenges. The strategies for success are broken down into the following six themes: 1) designing youth engagement strategies, 2) being creative and adaptable, 3) being a positive presence, 4) applying experiential learning techniques, 5) balancing the integration of culture with youth voice and 6) identifying partnerships and developing relationships with the community. The three themes relating to challenges were 1) community diversity, 2) social issues and 3) staff burnout. Recommendations are provided for issues related to programming and evaluation.