Introduction: Successful shared decision-making for critically ill intensive care unit (ICU) patients requires bidirectional communication. Through observation of ICU conversations, our study aimed to identify communication skill deficiencies in providers who care for patients in the ICU. Methods: This was an observational prospective study performed in a single urban academic medical center (671 beds) from June 2021 through August 2021. Twenty-three providers were recruited from medical and surgical ICU services (56 beds). Thirty-nine surrogate decision makers were identified. Provider skills were assessed using a customized observational tool that examined nonverbal communication, verbal communication, opening the discussion, gathering information, understanding the family's perspective, sharing information, reaching agreements on problems and plans, and providing closure. Results: Thirty-nine conversations were observed for six attending physicians, four fellow physicians, eight resident physicians, two nurse practitioners, and three physician assistants during the coronavirus 19 (COVID19) pandemic. A dedicated critical care provider engaged in 19 observed conversations; 20 discussions occurred with individuals rotating/consulting in the ICU. Communication skill did not depend on experience or area of expertise. Less than half of conversations achieved bidirectional communication proficiency. Scheduled conversations (n = 14) had significantly higher average communication scores than unscheduled encounters (n = 25). Conclusions: Superficial unidirectional communication with decision makers was commonly observed. Providers were less proficient at advanced communication skills needed for shared decision-making. We recommend that providers have more scheduled conversations, which were more productive in achieving bidirectional communication. A targeted simulation curriculum addressing these areas may improve patient, decision maker, and provider satisfaction, while promoting patient-centered care.