The current study examined associations between effectiveness supporting youth, connectedness with colleagues, and work-related well-being among after-school providers. We used a mixed method approach to gain an in-depth understanding of how effectiveness and connectedness may contribute to provider well-being. Participating after-school providers (n=34) completed a survey examining different aspects of effectiveness supporting youth (i.e., comfort promoting youth social-emotional outcomes, closeness or conflict with youth, ability to engage youth in programming), connectedness with colleagues (i.e., social support and social capital), and work-related well-being (i.e., work engagement, satisfaction, burnout, and stress). A subset of staff (n=11) also completed a follow-up interview to explore their experience of and self-identified facilitators and barriers to their effectiveness supporting youth, connectedness with colleagues, and work-related well-being. We used quantification of qualitative data and integrated data tables to consolidate qualitative and quantitative findings. Effectiveness supporting youth served as the most consistent predictor of work-related well-being across qualitative and quantitative data, including the capacity to build close and positive relationships with youth, engage youth in programming, and promote youth social emotional development. However, some providers also reported emotional fatigue from supporting youth experiencing stressful events, particularly in the absence of adequate resources and support from colleagues. Connectedness across colleagues was identified as a stressor when inadequate or ineffective support or communication was noted, but also as a buffer against stress for providers reporting sufficient and effective support and communication. Effective communication, bidirectional support relationships, and bonding social capital (e.g., trust and shared goals) were the most salient aspects of connectedness associated with positive work-related well-being. The current study illustrates pathways in which effectiveness and connectedness can promote or hinder work-related well-being among after-school providers, particularly the importance of building positive and effective relationships across staff and with youth while creating supportive work environments that include access to necessary resources for addressing youth needs.