We used problematic integration theory to examine challenging conversations between the hospice inter-disciplinary group (IDG) and hospice patients/families. The research questions guiding the study were (1) What are the underlying reasons for IDG team members' PI experiences when they interact with patients and their caregivers?, and (2) how do IDG members communicatively negotiate problematic integration when interacting with patients and their caregivers? In-depth focus group interviews with four IDGs and two certified nurse assistant teams revealed IDG members seem to experience the PI forms of ambivalence and certainty. There are two underlying reasons for IDGs' PI experiences: value conflicts and process conflicts. IDG members try to negotiate PI via the theme of verbal dance, or the direct and indirect ways IDG members educated family and caregivers. This education process includes disclaimers, following the lead of the family, trust building and using personal life experiences. Problematic integration theory helps shed light on the communicative nature of interactional dilemmas IDG members experience and how they negotiate these dilemmas in order to effectively support and care for hospice patients.