There are conversations we all know we need to have — but often put off for another time.

You know the conversation needs to happen. You’ve thought about it, maybe even rehearsed it. But finding the right moment or the right words can feel out of reach.

Whether you’re navigating care decisions with aging parents, major life transitions with your spouse, or financial expectations with adult children, the holidays present a unique opportunity to have important, albeit potentially difficult, conversations about the future of your family’s well-being.

These conversations require more than good intentions. They demand emotional intelligence, preparation, and practical strategies for working through complexity with the people who matter most.

During this presentation, Jennifer Landis-Santos, Cassaday & Company’s Career & Life Transitions Coach, shares practical techniques on how to build trust and have challenging conversations—while preserving the relationships that matter most.