OBJECTIVES: To explore the perspectives of intensive care unit personnel and patients' family members on challenges of family-clinician conversations and corresponding learning needs. RESEARCH METHODOLOGY/DESIGN: Cross-sectional survey study. SETTING: Two medical intensive care units of a German academic tertiary care hospital. MAIN OUTCOME MEASURES: Data were collected using an investigator-designed online survey with open- and closed-ended questions. Descriptive statistics were conducted to determine frequencies, free-text responses were analysed using directed qualitative content analysis. FINDINGS: The responses of 94 family members, 42 nurses, and 28 physicians were analysed (response rate: 45%). Regarding the clinicians' perspective, three main themes of challenges were deduced: ICU setting, Staff-related challenges, and Family-related challenges. Conversely, the majority of participating family members reported challenges both cognitive and affective in nature, e.g., remembering provided information or discussing the patient's prognosis. Most clinicians stated their need for a corresponding communication skills training to successfully navigate those challenges in clinical practice, particularly regarding conveying complex information, handling strong emotions, and managing family-clinician conflicts. CONCLUSION: The identified communication challenges underline the issues of family-clinician conversations that require improvement, making it possible to determine corresponding strategies to attain the desired outcome. Further research is needed to elicit best-practices of communication skills trainings for family-clinician conversations and its implementation in critical care settings. IMPLICATIONS FOR CLINICAL PRACTICE: These findings invite clinicians to engage in self-reflection to identify individually perceived communication challenges and learning needs. Faculty and healthcare institutions may further use these findings to conceptualise tailored communication skills trainings to contribute to the advancement in nursing and medical education.