This chapter highlights findings from five qualitative studies that have investigated aspects of professional mentoring using the Friends of the Children model. One study focused on better understanding the youth experience of being in the program. Two studies focused on the experiences of the mentors, and two studies focused on the roles of parents/caregivers. Unsurprisingly, a long-term relationship with a caring adult was an important element highlighted across the different studies. Findings from these studies have been used by Friends of the Children to adapt and improve their program across time. This learning process illustrates one way that child- and family-serving programs can use qualitative methods to listen and learn how to be more responsive to youth, how to be more inclusive of family/parents/caregivers, and how to attend better to the explicit needs of the front-line staff, in this case, professional mentors.