Many of the people I work with are not going to spend most of what they’ve accumulated.

They are going to leave it to children, to grandchildren, to a church or a cause they care deeply about. They are extraordinarily proud of the people who will inherit. They sacrificed for them — worked long hours, saved through lean years, built something so the next generation could start somewhere better than they did. By every visible measure, they succeeded.

And yet. Many of them tell me, quietly, that they’re not entirely sure their heirs are prepared to receive what’s coming. Not because of the kids — they love their kids. Because they’ve never had the conversation. The one about values. About what the money is for. About what the family stands for.

Helping clients have that conversation — well, with intention, on their own terms — has become some of the most meaningful work I do.

What’s Actually At Stake

When I started in this work fifteen-plus years ago, the conversation about inherited wealth was mostly about taxes. Set up the trusts, name the beneficiaries, run the numbers. Done.

Then the SECURE Act of 2019 changed the math. Most non-spouse beneficiaries can no longer "stretch" inherited traditional IRAs over their own lifetimes. They have to drain those accounts within 10 years of the original owner’s death.

Most of my clients pass these accounts to children who are themselves in their 50s and 60s — typically the highest-earning years of those children’s careers. So a $2 million traditional IRA can pass to a daughter at age 58, get drained over 10 years on top of her existing income, and lose hundreds of thousands of dollars to taxes that didn’t need to happen.

That’s the visible problem. There’s a deeper one.

The clients I serve almost universally tell me that their kids are already in a better position than they were when they started. They’re proud of that. But they’re less confident that their kids’ goals and values around money are what the parents would hope. They’ve built wealth without ever having a substantive conversation with the next generation about what it’s for.

That’s the gap I help my clients close.

Introducing the Family Conversation

One of the tools I use most often in my practice is what I call a Family Conversation. It’s a facilitated meeting with the next generation — children, sometimes grandchildren — in which the goals, values, and financial position of my client are shared in a way that brings everyone into a shared understanding.

It’s not a will reading. It’s a values reading. And it usually happens many years before any inheritance is on the table.

What Happens in the Meeting

Every Family Conversation looks a little different, but most include some version of the following:

  • A snapshot of the financial picture — not every detail, but enough that the next generation understands the scope of what their parents have built and what may eventually pass to them.
  • A clear articulation of values — what my client believes the money is for, what they hope it will accomplish, and what they hope it won’t enable in the lives of their heirs.
  • Specific intentions for each person or cause — not just "the kids will get equal shares," but why, and what for.
  • Open conversation — the chance for adult children to ask the questions they’ve never felt comfortable asking, and to share their own thinking about what wealth means to them.
  • A commitment to ongoing dialogue — the Family Conversation is rarely a single meeting. It’s the opening of a relationship between generations around a topic that families almost never talk about openly.

The Letter

I encourage my clients to pair the Family Conversation with something even more personal: a written letter to each of the important people in their life. Not a legal document. A letter — to a child, a grandchild, a sibling, a spouse, a friend.

What did this person mean to you. What do you hope for them. What you’d want them to know if you weren’t there to say it.

These letters are kept with the estate documents. They will be read by the people who matter most, in the moment those people most need to hear from you. I have heard, again and again, from clients’ children that these letters became some of the most treasured possessions of their lives.

Why This Work Matters

Money is a tool. It funds our lives, it funds our goals, it funds the things we care about. But when we’re at the end — when we’re truly at the end — we don’t look at our bank accounts. We look at the love in the room.

The work of legacy planning, done well, is the work of making sure both are there. The financial structure has to be right — the trusts, the Roth conversions to soften the SECURE Act burden, the charitable strategy, the beneficiary designations. But the financial structure is not the whole work. The relational work matters just as much. Sometimes more.

Children who inherit large sums of money without context, without conversation, without preparation, often struggle. Not always. But often. The wealth becomes a thing that happens to them rather than a tool they steward. By the second or third generation, in many families, it’s gone — and what was lost wasn’t just the money. It was the meaning.

That isn’t the legacy any of my clients want to leave. So we work, while there’s still time, to leave a different one.

Where to Start

If you’ve been quietly carrying questions about how to prepare the next generation — about whether your kids are ready, about how to talk with them, about what to write down — you’re not alone. Most clients I work with are carrying some version of those same questions, and most have been carrying them for a while.

The Family Conversation is one good place to start. It doesn’t solve everything in one meeting. But it opens the door, and it tends to change something for the better in every family that has one.

Whatever the love in the room turns out to be, it deserves to be there on purpose.

“We can’t perfect the world, but we can show up for the people in it — and hold ourselves to a standard worthy of the trust they place in us.” — Ashby Dawson

 

Auout the Author

Ashby Dawson, CFP®, AAMS™ is a Partner and Wealth Manager at Kingsview Partners in Amarillo, Texas. She works with Pantex employees and retirees on pension elections, Voya rollovers, tax planning, and retirement income and legacy strategy. She has been recognized as a Forbes Best-in-State Wealth Advisor and Best-in-State Women Wealth Advisor in 2022, 2023, and 2026.

Want to see what a multi-year Roth conversion and legacy plan would look like for your situation?

Schedule a confidential conversation: (806) 318-6820 | adawson@kingsview.com

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This article is for educational purposes only and does not constitute personalized financial, tax, legal, or estate planning advice. Tax laws change. Roth conversions create immediate tax liability and should only be undertaken after a careful review of your specific circumstances. Please consult a qualified fiduciary advisor and tax professional before executing any conversion or legacy strategy.