Contemporary society is characterized by social isolation, polarization, and increased mobility. For many families, naturally-occurring support systems are changing and possibly fading. When parents face child-rearing without adequate support networks, they experience high parenting stress, diminished health, and greater risk of maltreating their children. Children in socially-isolated families are prone to a range of social, emotional, and academic difficulties. Formal mentoring programs can help by connecting children with supportive nonparental adults, but the demand for mentoring outpaces program capacity, and formal mentoring programs are seldom designed to partner with parents. Additional, resourceful approaches are needed. In this study, we explored the potential for developing an approach that fosters parents’ capacity to be gatekeepers to their children’s adult support networks. We used a daylong collaborative workshop to partner with six parents from a low-income housing service and five youth-serving professionals from the community. Participants generated potential strategies by which parents can cultivate informal mentoring relationships and identified specific ideas for helping parents (a) see the value of actively seeking informal mentors, (b) recognize and manage potential risks, and (c) identify and make requests of potential informal mentors. Findings from our workshop were used to develop a Caregiver-Initiated Mentoring approach that could be utilized by clinical social workers and other helping professionals. The approach integrates our findings with empirical research from youth mentoring and conceptual underpinnings from parent help-seeking models, the Transtheoretical Model of Change, and Motivational Interviewing.