Providing telephone reassurance and check-in calls is a key strategy that is being widely used across the country to address social isolation among older adults and others, particularly in light of the COVID-19 pandemic. Recognizing that certain conversation skills can help to build trust and deepen engagement, ADvancing States partnered with Emergency Design Collective to create a new Conversation Tips Toolkit designed to support reassurance and check-in programs. This Toolkit is intended to benefit volunteers and staff who are participating in outreach calls with individuals receiving services. The Toolkit provides a collection of conversation tips in the areas of building trust, creating engaging conversation, understanding expectations and roles, and caring for yourself. The Toolkit is accompanied by a ‘Buzzfeed style’ quiz referencing The Golden Girls to serve as an entry point to the conversation tips. Guidance is provided in the Toolkit on how these materials can reinforce volunteer training.