Contemporary increases in chronic- and terminal- diagnoses among adults creates a demand for medical family therapists (MedFTs) to better-assist ill parents in preparing for and facilitating conversations with children. MedFTs must have skills, knowledge, and training in assessing when help is needed, and then engaging parents effectively in such conversations. As systems-trained providers, MedFTs functioning in medical contexts are well positioned to fulfill such tasks. This manuscript highlights educational/training and clinical foci essential toward MedFTs’ preparation for and conduct of this work. Ways to engage in difficult conversations with children are described across both general approaches and specific examples. Operational contexts such as integrating MedFTs into medical healthcare facilities, and financial considerations facilitative of these efforts, are also considered.