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Afterschool staff are critical to youth’s experiences in activities and shape what youth garner from activities. This study focuses on undergraduate students’ experiences working with adolescents in an afterschool activity through a community-university partnership in an effort to understand the challenges afterschool staff face and the strategies that helped them address those challenges. Undergraduate students, who are referred to as mentors in the activity, ( n = 15; 11 female; 8 Latine, 7 non-Latine) are the staff for a math enrichment afterschool activity serving largely Latine youth. The undergraduate students were interviewed to understand (a) the challenges they encountered when working with adolescents, (b) the strategies they leveraged to respond to these challenges, and (c) the extent to which the themes varied by racial/ethnic cultural backgrounds. Undergraduate students felt they experienced challenges with promoting motivation, teaching math content, navigating group instruction, building connections with adolescents, and establishing authority or respect. To respond to these challenges, they sought help from experienced undergraduate students, attended trainings, facilitated collaborative learning, integrated real-world examples, engaged in structured non-math related conversations, and leveraged students’ sociocultural assets. Results provide key stakeholders with insights on how to design trainings to better support undergraduate students who work with diverse youth.