A qualitative study of 61 youth receiving mandated services (child welfare, mental health, probation) or services where there were no alternatives (residential care for homeless youth) explored worker-client relationships from the perspective of young people themselves. Findings suggest three different but related roles played by workers that successfully engage adolescent clients: (1) ”Informal supporters” de-professionalize their role and flatten hierarchies, emphasizing empathy and enforcing few rules; (2) ”Administrators” enforce rules that are in the child’s best interest but do so with little emotional engagement; and (3) ”Caregivers” who hold reasonable expectations and impose structures but are flexible in their negotiations with youth when rules were broken. While youth spoke most positively about their workers when they acted as informal supporters, a deeper analysis of the data showed that youth also engaged well with workers who enforced rules when those rules were necessary for the child’s safety, applied flexibly, age-appropriate, and fit with cultural norms. Use of all three approaches to youth engagement may help workers create better therapeutic relationships with youth receiving mandated services.