Youth-initiated mentoring is an innovative youth care approach in which youth recruit supportive adults from their social networks as a mentor for youth and a partner for parents and professionals. This qualitative interview study documents what youth (n = 15) and parents (n = 13) from multi-problem families look for in a mentor, what mentors (n = 8) believe they have to offer, and whether what mentors believe to offer matches youth's and parents' needs. Youth and parents indicated that a strong connection and trust were most important, or even prerequisites, as youth who were unable to find mentors did not have strong relationships of trust. Youth and parents also voiced preferences for an understanding, sensitive mentor who offered youth perspective by providing support and advice and (according to some) setting rules. What mentors believed to offer matched youth's and parents' needs, suggesting that most youth successfully recruited suitable mentors.