Sufficient evidence suggests that building a helping alliance with youth is a viable strategy for addressing treatment needs and reducing delinquency. Strategies recommended in the development of strong helping alliances between youth and probation officers include hiring people with the right values and skills, training staff on the interpersonal skills needed to develop strong therapeutic relationships, matching staff and youth based on personality characteristics, interests, and skills, assessing staff’s capacity to develop strong therapeutic relationships, and supporting staff in their work. Further exploration is needed to gain more knowledge about the importance of building strong relationships with youth in order to challenge the current culture of many modern day probation agencies and deliver effective probation services. Over the past 20 years, much has been learned about the elements of effective correctional interventions through a body of literature known as “what works.” The primary foci within this literature are assessment, treatment models, and treatment setting. Relatively little is said about the specific knowledge, attitudes, and skill sets that correctional staff should possess to be effective change agents, or about the importance of the relationships that form between correctional staff and the offenders they serve. The purpose of this paper is to examine the role of the helping alliance in juvenile probation settings. Strategies for facilitating the development of the helping alliance and suggestions for future research are discussed. Figure, references