The purpose of this study was to explore how group leader affect impacted facilitation of a career education program. Through a case study design, data were gathered via focus groups and blog posts from 16 program staff members. Five major themes were derived, highlighting group leader affect and experience: Emotions During Intervention, Flexibility, Student Engagement and Connections, Support from Program Staff, and School Culture. The findings encouraged career educators to remain flexible when delivering programming, to consider regular evaluations of affect throughout career programming, and to acknowledge the reciprocity of engagement, affect, and programmatic buy-in between facilitators and participants.