All too often, when I am listening to friends and folks talk about their families and the state of the estate, I get some version of the sentiment “but I don’t even know how to start that conversation with my parents…” And I get it. It can be hard to have these critical conversations. On X, CPA Kurt Supe summarized it well:
“The biggest UBS finding on inherited wealth wasn't about taxes or trusts. It was about silence. The number one threat to a smooth handoff isn't a market crash or an estate mistake. It's that families don't talk.
Parents avoid the conversation, kids feel awkward asking, and the plan dies with the planner. You can build the perfect structure and still fail if no one knows it exists. When did your family last actually talk about the money?”
If the family treated the business of the family like a business, not having these conversations could be considered fiscal malfeasance. If the family treated the business of the family like a business, regular operating mechanisms like Annual Planning or Quarterly Business Reviews would be calendared and prioritized.
But here’s the secret: Healthy estate planning conversations are not a one-time, this-is-your-only-chance opportunity. Healthy estate planning is an ongoing and regular topic that can be done at the dinner table (or the hospital bed…or the funeral parlor…you choose). And we can all start with asking questions of Mom and Dad, such as:
- Big Picture: How do you envision the next 3-5-10 years playing out?
- Bucket List: What else do you want to do or accomplish in the next few years?
- Time: If you could spend more time with family, friends, and the Next Generation, what would you want to do?
The point of these questions is not to talk about money. Eventually that will surface, but only relative to the rest of life and hopes and dreams, and not as the goal of the conversation. Yes, we are the Sandwich Generation, and yes, we are now the adults for the family. This role reversal is hard but can be managed with compassion and understanding by being curious and open to Mom and Dad’s wishes.
“The plan dies with the planner.” Brutal. We deserve better. Mom and Dad deserve better. The Next Generation deserves better. And we can ensure we help ourselves and our families. We can move us all forward…