Adolescence is a time of significant growth and change. Thus, adolescents are uniquely vulnerable to mental health conditions and other high-risk behaviours that may impact their health. Early identification and treatment of these conditions can reduce potential morbidity and improve future health outcomes for adolescents. Due to their frequent contact with adolescent patients, family physicians are in a unique position to identify adolescents that may need help. The HEADSS framework (Home, Education, Activities, Drugs, tobacco, and alcohol, Sexuality and relationships, and Suicide and Depression) is a helpful tool to facilitate communication and assess adolescents’ psychosocial well-being. The HEADSS framework is structured to transit from less sensitive to more sensitive topics as rapport is established and cover topics important for adolescent health. Adolescents generally respond best to physicians with an empathetic and non-judgemental approach. Confidentiality and exceptions to confidentiality should be addressed with the adolescent and their caregiver prior to starting the HEADSS assessment. If any concerns are noted on the HEADSS assessment, referral to other services may be required for further assessment and intervention.