One of the most common things we hear from people who unexpectedly inherit money isn’t excitement. It’s this—I wish they had just talked to me.
Not about the money, necessarily, but often and at least about the purpose behind it. What it meant to them. About the relationship. The money, it turns out, is almost secondary to the conversation that never happened.
Ashley Quamme and I have been spending a lot of time lately talking about windfalls—inheritances, business sales, IPO paydays—and specifically about the conversation that needs to follow. Because whether you’re an advisor helping a client navigate this or a parent sitting on information you’re not sure how to share, there is a conversation coming. And how you handle it matters. But don’t worry, we’ve got your back.
First, Let’s Normalize How Weird This Is
The great wealth transfer is a phrase that gets thrown around a lot in financial planning circles—somewhere between seventy and ninety trillion dollars moving between partners and generations over the coming decades. It sounds massive, and it is. The wealth transfer is also deeply unevenly distributed. About 50% of it will go to roughly 2% of households. The average projected inheritance from most boomers to lower generations is less than $50,000—and even that number is being dragged upward by a small number of ultra-high-net-worth families.
What this means practically is that most people don’t have a lot of lived experience with windfalls. They haven’t watched their parents navigate one. They haven’t practiced the conversation. This doesn’t happen to their neighbors or friends with much regularity. And so when it happens—whether it’s an inheritance, a business sale, or something else entirely—it genuinely feels weird. Even when you knew it was coming.
Think about what it would be like to go from being someone who makes a good living and budgets carefully and thinks in trade-offs, to suddenly having ten million dollars sitting in an account. Weird. The friction of a budget isn’t just an inconvenience—it’s actually a structure that helps most people feel grounded and purposeful. When that disappears overnight, even in the best possible way, people often feel surprisingly unmoored. And that’s before they’ve said a word to their kids.
So if you’re an advisor and your client seems more anxious than excited about a windfall, that’s not unusual. And if you’re a person sitting with this and not quite knowing where to start—that’s completely normal too.
This Is Not One Conversation
The single most important thing Ashley and I want you to hear is this: you do not have to figure it all out in one sitting.
There is no 60-minute conversation that resolves everything. There shouldn’t be. The pressure to get it all right, all at once, in a single family meeting is one of the main reasons people avoid having the conversation at all. So the first thing to do is give yourself permission to let this unfold over time.
Once you accept that this is one of many conversations—not the conversation—the starting point becomes a lot less daunting. You’re not announcing a verdict. You’re opening a door.
Before You Say Anything: Get Aligned
If you’re in a partnership, the conversation starts there. Before you talk to your kids, get on the same page with your spouse or partner about what you actually want to share, how much, and when.
This sounds obvious, but it’s commonly one of the place things go sideways. One partner is a jump-right-in type who wants to lay it all out immediately. The other wants to wade in slowly, inch by inch. Neither approach is wrong—but if you haven’t talked about it ahead of time, you’ll find yourself contradicting each other in the middle of a conversation you can’t take back. And potentially cause even more confusion and emotional stress.
If you’re working with a financial advisor, bring them in before you have this conversation with your family. Not to let them run it, but to help you think through what’s actually ready to be shared and what isn’t. There’s often more uncertainty in the early stages of a windfall than people realize—amounts that aren’t fully settled, plans that aren’t finalized—and sharing incomplete information can create more confusion than it resolves.
Think Backward From the End
The main reframe from the conversation between Ashley and I is this: before you plan what you’re going to say, decide how you want everyone to feel when the conversation is over.
Do you want your kids to leave feeling informed but not overwhelmed? Reassured that there’s a plan, even if they don’t know all the details yet? Invited into an ongoing dialogue rather than handed a finished document? Whatever your answer, working backward from that outcome will tell you how much to share and how to frame it.
This also means knowing your audience. If you have one child who processes out loud and asks ten questions on the spot, and another who goes quiet and needs a few days before they can respond—those two people need slightly different versions of the same conversation. Not different facts, but different pacing and different amounts of information at once. This is the first conversation of what will be an ongoing discussion; it is worth taking the time to plan it out.
A Framework for Opening: Ask, Tell, Ask
Once you’re in the conversation, there’s a simple structure—borrowed from medicine—that we find incredibly useful. It’s called Ask, Tell, Ask, and I first learned it from Rose Zealand.
The first Ask is an assessment. Before you launch into what you want to share, find out what they already know. “You know that we sold the business—what’s your sense of how that went? What do you already know about where things stand?” This does two things: it tells you where to start, and it opens a channel for them to share what they’re already thinking or feeling—including any confusion or worry that’s been sitting below the surface.
Next, Tell: this is where you share the information. Plain language, appropriately scoped to what you’ve decided is right for this conversation. Not everything at once. Not the full estate plan on day one. Just what’s true and relevant and ready to be shared right now. It often starts by answering whatever questions was just posed during the initial ask.
The second Ask is where you close the loop. “What questions do you have? What else would be helpful to know more about? How does this land for you?” This step gives the other person a chance to process out loud, surface confusion, and feel like a participant in the conversation rather than a recipient of information. You want to encourage your kid, or whomever you are telling, to essentially repeat back to you what they now know and expand on it via another question, emotion, or idea.
What I love about this framework is that it works whether you’re the parent, the advisor, or even the adult child who’s trying to figure out how to ask their own questions. It keeps the conversation from becoming a one-way announcement and makes space for it to be what it actually needs to be: a dialogue.
Build a Roadmap, Not Just a Moment
A windfall conversation isn’t an event. It’s a timeline.
Ashley does an exercise with clients where they co-create a map of conversations—not a script, but a rough sequence of what gets shared when, and what the goal of each conversation is. Maybe the first conversation is just opening the door: “We’ve received some money and we want you to know about it. We’re still figuring out what it means for our family and we’ll keep talking as we do.” The second conversation might be about the estate plan at a high level. A third might bring in the adult children as active participants in thinking about how the family uses or preserves the wealth going forward.
Having a map does something really important: it reduces the pressure on any single moment. And it lets you gauge, along the way, how each family member is processing things and what they’re actually ready to hear.
The Fears That Look Like Control
This is the part I want to spend a moment on, because it comes up constantly and I think it often gets misread.
When parents are reluctant to share information about a windfall—when they hedge, delay, or give only partial information—it often gets labeled as wanting control. And sometimes that’s fair. But in my experience, what’s more often underneath it is fear. Very understandable, very normal fear.
Fear that the money will change their children’s motivation. Fear that future partners will enter the picture for the wrong reasons. Fear that the family story—the work, the sacrifice, the specific shape of how this wealth came to be—won’t be honored once it’s passed on. Fear that their children will be overwhelmed, or will make decisions they’ll regret.
These fears are worth naming out loud, first to yourself and then eventually in the conversations you have. Because parents who only plan from a place of fear—who structure everything around what could go wrong—tend to have very different conversations than parents who also make space for hope.
Hope and Cope
I’ll leave you with a great fear reframe we like for this moment.
For every fear you have about this money and what it might do to your family, there is a corresponding hope. The fear that your child becomes financially reckless has a flip side: the hope that this money gives them freedom and security and options you didn’t have. The fear that the family story gets lost has a flip side: the hope that it carries forward in how your children choose to live and give and build.
If you were to write out your fears in one column and then rewrite each one as a statement of hope in the other, something shifts. You’re not ignoring the fears—they’re real and they deserve attention. But leading with hope opens a different kind of conversation. Instead of a conversation organized around protection and limits and what won’t be allowed, you get a conversation organized around purpose: What do I dream for you? What does this make possible? How do we talk about that together?
And that conversation—the one grounded in hope—is the one that gets buy-in. It’s the one that adult children actually want to be part of. It’s the one that makes the money feel like a relationship rather than a transaction.
The great wealth transfer is coming for a lot of families. The conversation doesn’t have to be as hard as it feels. But it does have to happen.
Ashley Quamme and I talk about conversations like this one regularly on our series Relevant & Relational, part of the Beyond the Plan Solutions YouTube channel. If this is something you’re navigating—as an advisor or as a person—feel free to reach out. We’d love to keep talking about it.
At Beyond the Plan(R) Ash and I also work with families and advisors, helping them navigate conversations like this with greater clarity and support.
If you are interested in working with us. We are interested in hearing from you.
