There’s no way around it—estate planning conversations can bring up some deep, often generational conflict. But if we don’t talk about it, that conflict doesn’t disappear. It just shows up later. In court. In arguments. In estrangements that could’ve been avoided. The truth is, most of the time, the issue isn’t really the estate plan. It’s the communication—or lack of it.
This is where advisors can do more than draft paperwork. We can facilitate peace.
Start by Changing the Room
When I work with families, we don't sit around a kitchen table. That’s the family’s natural environment—and for many, that’s where dysfunctional communication thrives. Instead, we shift the setting. We model what healthy, respectful communication looks like. And we set ground rules that prioritize listening, reflecting, and giving each person space to speak without interruption.
If there’s a known history of family dysfunction, I don’t pretend that a checklist of financial documents will fix that. We bring in professionals trained in family systems and conflict resolution. Because until each person feels seen, heard, and safe, the conversation doesn’t move forward—it just loops in frustration.
It's Not Just About the Will. It’s About the Why.
I worked with a blended family where the father, a proud Latino man, simply would not move forward on estate planning. No matter how many facts or financial benefits we laid out, he said no. But it wasn’t fear. It wasn’t ignorance. It was his story—his lived experience. He grew up hearing about shady lawyers, about families being torn apart after death, about broken promises.
He wasn’t being stubborn—he was defending his roots. When we stopped trying to “educate” him and started listening to his story, everything shifted. We gave him permission to be exactly who he was, to explore where his beliefs came from, and only then could he reframe his story. That’s when planning became possible.
This happens all the time. In another case, I saw three generations of a wealthy family come to a standstill. Grandpa made his millions in oil and gas and believed in wealth preservation above all else. His grandchildren, raised in comfort, were deeply committed to climate action and didn’t want to inherit money tied to fossil fuels. Same last name. Same DNA. But completely different lived experiences. Until they were helped to hear each other—not just respond, but really hear—they couldn’t move forward.
Cleaning Up the Mess That Wasn’t Yours
Yes, I’ve cleaned up many estate planning messes. It’s more common than you think. Clients come in with partial plans—maybe they have a will but no insurance, or they started but never finished working with an attorney. Often they’ve paid retainers to professionals and then walked away before anything was signed. Why? Because it was overwhelming. Because someone was pushing too hard. Because no one slowed down to ask, “What’s stopping you?”
The fear of mortality, the weight of family expectations, the belief that this can wait—these all block people. And if we’re not asking the deeper questions, we’re not helping.
Trusts and Wills Don’t Fix Everything—Relationships Do
You can’t reduce conflict with documents alone. An advisor has to know what keeps their client up at night. What they fear losing. What legacy they dream of leaving. Until you have those answers, you’re just pushing paper.
Trusts are technical. But trust between people—that’s what matters most.
We give clients permission to talk about death, fear, resentment, love, control, and family. That’s where estate planning becomes real. That’s where it stops being just a legal task and starts becoming a gift.
Practical Tools That Make a Real Difference
I often introduce something that sounds simple—a “talking stick.” One person speaks at a time. No interruptions. Then, the next person doesn’t respond—they summarize what they heard. This completely changes the dynamic. It shifts the goal from rebuttal to reflection. It creates a pause, a moment of validation. And being heard—really heard—is one of the most healing things we can offer another person.
When people feel safe, they can communicate. When they communicate, estate planning can begin—not from a place of pressure or fear, but from purpose.
Jonathan Kolmetz is a Licensed Professional Counselor, Financial Advisor, and President of Oaks Wealth Management. He holds an MBA, a Master’s in Clinical Mental Health Counseling, and is passionate about helping families rewrite their money stories.