Accounts of mentoring relationships inevitably draw attention to hierarchies of expertise, knowledge and learning. While public concerns about both the risks and benefits for young people of social media, little attention has been given to the nature of the mentoring role that parents and families play alongside of schools. This conceptual paper explores models of mentorship in the context of family dynamics as they are affected by social media use. This is a context that explicitly disrupts hierarchical structures of mentoring in that new media, and particularly social media use, tends to be driven by youth cultural practices, identity formation, experimentation and autonomy-seeking practices (see for example: Robards; boyd; Campos-Holland et al.; Hodkinson). A growing body of research supports the notion that young people are more skilled in navigating social media platforms than their parents (FOSI; Campos-Holland et al.). This research establishes that uncertainty and tension derived from parents' impression that their children know more about social media they do (FOSI; Sorbring) has brought about a market for advice and educational programs. In the content of this paper it is notable that when family dynamics and young people's social media use are addressed through notions of digital citizenship or cyber safety programs, a hierarchical mentorship is assumed, but also problematised; thus the expertise hierarchy is inverted. This paper argues that use of social media platforms, networks, and digital devices challenges traditional hierarchies of expertise in family environments. Family members, parents and children in particular, are involved in ongoing, complex conversations and negotiations about expertise in relation to technology and social media use. These negotiations open up an alternative space for mentorship, challenging traditional roles and suggesting the need for cooperative processes. And this, in turn, can inspire new ways of relating with and through social media and mobile technologies within the family.