Despite advances in evidence-based practices (EBP) to support HIV prevention and treatment, youth ages 13-24 experience significant disparities in HIV risk and outcomes. An important factor in this disparity is poor EBP implementation, yet implementation research is limited, particularly in youth-serving settings. This study used the Exploration, Preparation, Implementation, Sustainment (EPIS) framework to guide the implementation of four Motivational Interviewing (MI) and MI-framed interventions into youth-serving HIV prevention and treatment settings. Key stakeholders (n = 153) across 13 sites completed pre-implementation interviews. Stakeholders' comments identified two critical factors for effective implementation: fit with the patient population and provider receptivity, including concerns about scope of practice, buy-in, and time. Stakeholders recommended strategies for structuring training, fidelity monitoring, and facilitating implementation including engaging informal leaders, collaboratively developing the implementation strategy, and site-wide implementation. Results highlight the importance of pre-implementation contextual assessment and strategic planning for identifying provider concerns and developing responsive implementation strategies.