Surgeons treating critically ill patients must work with family members making medical decisions for the patient. These surrogate decision makers depend on providers' high-quality communication and empathy to facilitate medical decisions. There is growing evidence of poor quality of communication and delayed family engagement in the intensive care unit, and of a decline in empathy over the course of a surgeon's clinical training. The aims of this study were to: (1) describe family understanding of patient prognosis among those admitted to our Trauma Intensive Care Unit (TICU), compared to the surgeon's assessment, and identify factors influencing the congruity of family-surgeon understanding ("congruence"); (2) characterize resident mentoring regarding difficult healthcare discussions and suggest adaptations to our communication program to address identified performance gaps. Level I TICU in an independent academic medical center. A qualitative research approach was valuable to discern the complexities of family understanding during highly stressful conditions. We enrolled adult family members of TICU patients, life expectancy <1 year, per attending. Using in-depth interviews we explored the family's experience with providers and the hospital system, and factors influencing understanding of the patient condition and decision making. We interviewed the surgical attending and/or resident separately to ascertain their perspective of the patient's condition and their experience with the family, as well as communication style, training, and influences on their approach. Interviews were audiotaped and transcribed. Using the systematic, multistep, rigorous coding process of grounded theory, we identified a range of experiences and common themes, and developed theories and hypotheses regarding factors influencing our outcomes of interest. We enrolled, coded, and analyzed 31 interviews from 16 cases; the data painted a broad description of a complex situation. We developed a conceptual model of our hypothesized factors influencing congruence (Figure). Our data suggest that congruence varies widely, and is influenced by family-surgeon engagement quality, information accessed from other hospital and personal sources, and, significantly, hospital system factors. Family-surgeon engagement quality is influenced by family and physician factors, case complexity, and myriad hospital factors. Both "physician factors" and "family factors" include previous experience, personal history, and beliefs, as well as dynamic factors such as current experiences and stress level. We identify several opportunities to improve congruence by adapting our resident communication training program: providing practice assessing family knowledge, expectations, and current understanding of information shared, and focusing on building trust. Surgical residents receive formal communication training and focused mentoring to gain important skills; however, family members' understanding of their loved one's critical condition is influenced by myriad hospital system factors beyond case complexity and surgeon communication skills.