While most older adults have thought about their future care needs, few have discussed their preferences with family members. We interviewed older persons (24), adult children (24), health professionals (23), and representatives of stakeholder associations (3) to understand their views and experiences on later life care (LLC) planning conversations, in terms of (a) their respective roles, and (b) barriers and facilitators that should be taken into account when having these conversations. Roles described included that of information user (older persons), information seeker (family members), and information provider (health care providers). The study identified practical and emotional considerations relevant to LLC planning conversations. This study found strong support for planning for LLC before the need arises, as well as important potential benefits for older adults, family members, and health professionals. There is interest in, and need for, resources to guide families in LLC planning.