HIV/AIDS prevention projects utilizing indigenous outreach workers often rely on the life experiences and skills of the staff to structure the intervention, without grounding in theory. However, to be most effective, community outreach projects which target harder-to-reach high-risk populations should both utilize and enhance the natural strengths of indigenous field workers' experience and style of interaction, while guiding intervention content with theoretical rigor. In this paper we demonstrate that the challenge of successfully integrating a theoretically guided program design with field staff's credibility with, and sensitivity toward, drug-using clients can be practically and satisfactorily met through appropriate training. This training is an important investment for better utilizing valued and scarce prevention resources. The Philadelphia site of the AIDS Evaluation of Street Outreach Project (AESOP), a cooperative agreement of the Centers for Disease Control and Prevention, designed and implemented staff trainings to reflect the enhancement of the outreach program by the Stages of Change model. Through these trainings, the outreach workers have learned to integrate their natural street and intervention skills into the structure of a theoretical framework. This paper presents specific training components, relevant issues within these components, and areas for evaluation and feedback.