The recent UK policy of austerity has resulted in significant funding reductions for a wide range of leisure services. Indeed, specific preventative services that operate within the context of participants’ leisure activities, such as community sport coaching and youth work that focus on positively intervening and preventing anti-social behaviour, have continued to decline, thus resulting in a range of negative consequences for disadvantaged young people. Given that both fields share a history and objectives by using leisure and recreational activities to support behavioural change, this paper explores the potential for shared good practices, methods, and possible guidelines/recommendations for practitioners through examining parallels in applied practice between community sport coaching and youth work. Using a qualitative method, data was collected via semi-structured interviews with 10 community sport coaches and youth workers. The findings suggest that both fields share significant similarities in approach and practice, and that meaningful approaches to facilitating engagement with service users can be made through actively promoting empathy and “relatability”, including sharing experiences, jointly constructing interactions, and regularly monitoring and supporting young service users.