Communicating effectively with children is fundamental to educational practice. As children spend a significant amount of time in education settings, there is increasing pressure on educators to promote positive mental health and wellbeing, participate in prevention of mental ill health, and work with children diagnosed with existing mental health conditions. However, communicating about mental health, wellbeing, and emotional regulation with children, and generally supporting those with need, can be a challenge. Educators need a communication toolkit to help them build their confidence and competencies in engaging in sensitive and critically important conversations. To develop this toolkit, we spotlight the communication practices used by mental health practitioners in clinical settings, translating key messages for educators. In this chapter we show how question design is instrumental for engagement, and detail ways to manage the complex endeavour of asking children about emotions, feelings, and wellbeing. The data illustrate some of the discursive techniques used by adults when communicating with children about mental health and wellbeing, illustrating examples of good practice for educators. To demonstrate this, we utilize excerpts of data from the assessments data and translate clinical practice into educational knowledge.