Currently, single loop learning is the predominant method of problem solving orientation engaged in by healthcare institutions. This mode of learning is not conductive to fostering needed communications between health care providers and terminal patients. Reflection in action, second loop learning, focuses on deep listening and dialogue and can be critical in opening communications paths between the dying patient and his or her caregivers. This article discusses organizational learning theory and applies the theories double loop learning technique of reflection in action to end-of-life care. The article further explores an exemplar of reflection in action in a Palliative Care Program, and end-of-life home care program at Kaiser Permanente. In order to more effectively meet the needs of terminally ill patients, greater efforts are needed to incorporate second loop learning into the practice of those caring for these patients.