Understanding possible barriers and facilitators to effective implementation of evidence-based interventions to help high-risk youth prevent and manage HIV is crucial for their scale-up. This manuscript analyzes qualitative interview data collected during the early phase implementation of a motivational interviewing (MI) based intervention at 10 HIV care clinics in the United States providing services to youth. Using the Exploration-Preparation-Implementation-Sustainment (EPIS) framework to understand the implementation and the dynamic adaptation process (DAP) model to balance notions of intervention fidelity and flexibility, providers and stakeholders at each site (N = 97) were interviewed prior to implementation to gather their perspectives on organizational readiness for the intervention, as well as provider and client characteristics. The interviewers summarized their experience with rapid feedback forms (RFFs). Data extracted from the RFFs highlighted anticipated barriers to and facilitators of the proposed MI-based intervention, with the EPIS framework used to organize these findings. Study findings illustrate the inner and outer contextual factors that affect implementation and denote the points at which the MI-based intervention may be tailored to fit the unique context of a clinic while remaining faithful to the intervention’s original design.