Young people with mental health needs are often cared for on children’s wards by generalist children’s healthcare professionals (CHCPs). Generalist CHCPs find these encounters challenging and difficult but they are viewed as an opportunity to improve the healthcare offered to these young people. The authors secured funding from Health Education South London to design and deliver interactive workshops to improve the communication skills of CHCPs with adolescents in challenging circumstances. In this article, the authors outline the design and content of the workshops and discuss how the workshops explore and challenge the attitudes the participants have that could prevent a young person from seeking support or engaging with professionals. They also describe how the workshops have improved generalist CHCPs’ confidence and communication skills when talking with young people and how participants now use these encounters as an opportunity to improve healthcare for children and young people.