You’ve worked with a client for 15 years. You know how she thinks about risk, what keeps her up at night and which grandchild she worries about most. Recently, the conversation of legacy planning came up, and you both decided it would be a good idea for her son to be brought into the conversation. The son is agreeable, and during the meeting you find him to be polite. He even asks a few good questions. But halfway through the meeting, you realize he’s deciding whether he’ll still be your client when she’s gone, and you’re not getting the best feeling.
Why trust doesn’t transfer on its own
Trust gets built person by person, and each generation brings its own money story to the table. The generation that built the wealth often wants to protect it. The generation receiving it may want to grow it, give it away or use it in ways their parents never would. Both perspectives make sense given where each person started.
The challenge is not understanding the differences between the generations but learning how to keep and earn the trust of both. Because while the assets may get passed down by your client, it doesn’t mean the trust they have in you does.
What each generation is listening for
When you sit with a multigenerational family, each person is listening for something different.
- The generation that built it is listening for security. Will my wishes be understood and protected? Will my family be OK?
- The generation receiving it is listening for freedom. Will I get my own relationship with money, or am I inheriting my parent’s blueprint?
Both needs are valid, and both can live in the same family at once.
Two things to try
1. Meet the next generation on their own
With the parents’ blessing, invite the adult children to a one-on-one conversation. Ask about their goals, their worries, who they are as people. Get to know them. You might ask what they noticed about how their family handled money growing up, or what they’d want an advisor to know before working together. For many heirs, this is the first time they see you as their resource. This is your opportunity to begin building the trust bridge with them. Afterward, send a short note that mentions something they shared. That small bit of follow-through tells them they were heard.
2. Questions to explore
Start with the parents and ask, “What do you hope this money makes possible for your children?” With the adult children, ask, “What will this money represent to you? What are you hoping it will allow you to do?” You’ll likely hear different answers. Resist the urge to reconcile them. Each one tells you what trust will look like for that person.
Keeping the conversation going
Families will rarely see money the same way across generations, and they don’t have to. What helps is a place to keep talking about it, and someone each of them trusts to keep that conversation going.
Think of the family you’ve served the longest. If the parent passed away tomorrow, would the children call you? And would you know what to say if they did?
Ashley Quamme is the founder of Beyond the Plan and host of the Planning & Beyond podcast. She works directly with financial advisors’ clients on the conversations that are more about the family than the portfolio and coaches advisors on the conversations they find hardest. She is speaking at the 2026 MDRT EDGE on “The irreplaceable advisor: 3 relational skills that AI can’t replicate.” If you’re attending, come say hello. Learn more at beyondthefp.com.
