Undergraduate agricultural leadership education opportunities are prevalent and growing. However, additional attention should be placed on the quality of educational leadership experiences. The purpose of this study was to explore how the context of a learning experience impacts student application of team leadership skills. The findings and implications of this study are reported in three themes: (a) contextual dimensions of educational experiences, (b) agricultural disconnect, and (c) team leadership skill application. Recommendations for practitioners include providing students with real-life leadership skill application experiences, regulating assignments to have agricultural connections, and integrating opportunities for student reflection. Future research should consider questions such as: (a) what other educational leadership experiences may have considerable learning impacts? and (b) what other pedagogical methodologies are useful in teaching agricultural and team leadership education?