Multiple studies reveal that the healthcare needs of chronically ill older adults are poorly managed and often have devastating consequences. This paper examines available evidence related to improving care management and outcomes in this vulnerable patient group. Findings reinforce the need for enhanced patient engagement and suggest comparative effectiveness research as an important and immediate path to optimize patient–clinician partnerships. An ongoing study in care management is described as an example of such comparative effectiveness research. An overview of the barriers to implementation of evidence-based strategies related to health literacy, shared decision-making and accountability for self-management is provided, followed by a set of recommendations designed to facilitate comparative effectiveness research that advances engagement of high-risk older adults and their family caregivers.