Persons with chronic illness frequently find they need to navigate the health care system but are ill equipped to do so. Using interview data from 32 participants, this study explored patients' experiences with a coaching intervention that provided patients with support and tools to enhance self-management during care transitions. The findings suggest the efficacy of the model in enhancing self-management, particularly because it fostered the perception of a caring relationship, leading to greater patient investment in the program. Future research should seek to explore which patients are most ready and able to benefit from this type of intervention.