Objective: The purpose of this study is to explore whether participation in a youth leadership development programme proved effective in the development of four foundational leadership components (i.e., social, and emotional intelligence, collaborate, articulate, insight and knowledge), within a specific community based sports setting and whether participants utilised these skills in other life domains. Research Design: A qualitative case study methodology. Method: Nine semi-structured interviews, participant journals, mentor notes. Data Analysis: Involved an iterative process of open coding, axial coding, and theoretical integration, using Braun and Clarke’s (2006, 2019) six step thematic analysis framework. Results: The findings of this study revealed that a variety of mechanisms and factors contribute to the development and transfer of key life skills and leadership capabilities. Such antecedents were underpinned by multiple interrelated factors (e.g. learning context, opportunities to practice, individual learner, time, programmatic features, transfer context factors and other social agents). While some skills developed better (self-perception, teamwork, decision making, communication and leadership skills) than others (critical thinking and problem solving), the predominant modes of skill transfer found were proximal transfer (in-programme outcomes) and distal outcomes (out of programme outcomes – predominantly sport and college). The findings also revealed that the socioecological context in which the leadership programme was facilitated in provided supportive conditions for positive youth development outcomes. This study illustrates the complexity of exploring transference through a multiple of underlying factors that are interrelated in the transfer process. Taken together, findings indicate that life skill, leadership development, and transfer is most effectively promoted through a multi-systems approach.