How to Talk to Clients About Inheritance (No Tricks or Treats Necessary)

On Halloween night, the front porch is the friendliest spot on the street. The doorbell rings every few minutes. A neighbor you usually just wave to stops by for a real conversation while the kids compare candy on the steps. For one night, people happily trade what-ifs and spooky stories with folks they barely know.

Inheritance is the what-if most families still leave alone. According to Trust & Will's 2026 Death & Inheritance Report, only 8% of American families say a financial advisor, attorney, or other professional started their conversation about inheritance. Everyone else is waiting for Uncle Rick to bring it up over Thanksgiving pie, or for a crisis to force it.

So I asked the Trust & Will Financial Advisor Contributor Panel to go first. When you bring up inheritance with a client, what do you say first? And what usually happens next?

The best way to open the inheritance conversation with clients is to start with the people they care about and let the paperwork follow. For financial advisors, each answer below is a first line you can borrow, and most of them make room for the next generation long before any wealth transfer happens.

Six Openers to Borrow

• Bob Chitrathorn: “If something happened to you tomorrow, would your family know what you wanted them to do?”

• Al Faber: Who will be responsible for taking care of your parents' estate when the time comes?

• Matthew Veland: Do you have a spooky estate planning story of your own?

• Matt Koppelman: What would you regret not having taken care of if you only had one day left to live?

• David Wright Jr.: “What do you want your legacy to be?”

• Lisa White Burns: “Have you had a conversation with your family about what you want them to know—not just what you want them to receive?”

The stories behind each one are below, along with what tends to happen after the client answers.

If Something Happened Tomorrow, Would Your Family Know?

Bob Chitrathorn, CPFA®, Co-Founder and CFO of Simplified Wealth Management, has retired one opener for good: “What happens when you die?” That question tends to stop a meeting cold, which is a little too on theme for October. He asks something more practical. “If something happened to you tomorrow, would your family know what you wanted them to do?”

“That question usually changes the conversation,” Bob said. “Most people have thought about inheritance more than they admit, they just haven't talked about it out loud.”

What usually happens next, he said, “is the client starts thinking beyond the numbers.” Clients start saying what they actually want. “I don't want my kids fighting over this,” one might say, or “I'm not sure my son is ready to manage that much money.” Bob's read on that moment is simple. “That's where the real planning starts.”

From there he walks clients through three questions: “Who needs to know?” “What could cause confusion?” and “What needs to be explained?” The last one can carry the most weight. “Sometimes the most important thing a client can leave behind isn't another legal document, it's some context around why they made the decisions they did.”

Who Will Take Care of Your Parents' Estate?

The word “inheritance” makes some clients flinch. Al Faber, CFP®, ChFC®, CLU®, Founder of DIWY Financial Planning, has a theory about why. “I think people see it like they don't want to seem greedy, like, what am I getting?” he said on our October call.

So he comes in from the other side. He asks about the client's parents and grandparents, and about siblings if the parents are living, to get the family context first. Then he asks who will be responsible for taking care of the parents' estate when the time comes.

That answer does a lot of work. “That usually will lead me to the discussion around who gets what, who's in control,” Al said. It's a smart way in. Trust & Will's report found that 36% of Americans name a parent as the hardest family member to have this conversation with. Al gives the client room to talk about a parent long before anyone has to say “what do I get?” out loud.

He also draws out the family tree with clients, and the holidays make that easy, with relatives in town and old stories already circulating. “Talking about the family starts to engage people in these conversations,” he said.

Do You Have a Spooky Estate Planning Story?

Matthew Veland, Financial Planner with Prudential Advisors, has the most seasonal opener on the panel. When a client hesitates, he leans into it. “I ask them if they have a spooky estate planning story of their own,” he said. On our Contributor Panel call, he compared it to an easy pitch. “I'll give an underhand and then they'll knock it out, single, double, whatever.”

Most swings come with a story. “Nine times out of ten, there's a story that negatively impacted the family,” Matthew said. “This usually prompts action on the clients' part.” The report backs him up: 41% of Americans say money, an inheritance, or an estate has affected a relationship in their own family, and 17% say it did permanent damage.

He doesn't wait for October to bring it up, either. “Discussing inheritance is just part of my process,” he said. It comes up in a dedicated meeting when a client first signs on, and again every year at an estate planning check-in, when he asks whether any major life events have happened. Our Estate Planning Awareness Week roundup has more panel ideas for that yearly meeting.

For advisors who work with Trust & Will, the advisor dashboard makes that yearly check-in easier to prepare, since it shows which clients have signed up and which have finished their plans.

What Would You Regret Not Having Taken Care Of?

Matt Koppelman, CFP®, WMCP®, Co-Founder of Precision Wealth Planners and Financial Planner with Prudential Advisors, starts far from the paperwork. He follows George Kinder's approach to financial planning, “which starts with what someone wants their life to look like before we get into the numbers,” he said. “Estate planning usually comes up on its own that way.”

One question he borrows from Kinder asks what a client would regret not having taken care of if they only had one day left to live. It sounds heavy. The answers are mostly about people. “Along with the trip they wish they took, people usually bring up a son they worry about, a parent they support, or a grandchild they want to help with school tuition,” Matt said.

Each of those people comes with a decision attached: who receives what, when, and who handles it. Matt would rather begin with the people. “The conversation is easier to have when you're talking about real people instead of documents and legal jargon.”

What Do You Want Your Legacy to Be?

David Wright Jr., Managing Principal of WrightWay Legacy Services, opens with two questions: “What do you want your legacy to be?” and “What do you want to be remembered for?” They give people room to talk about what they have built and the values they hope to pass forward. Then the questions get practical, from whether a family home matters to who should make decisions if the client can't. (For that last one, our guide to choosing a family decision-maker is a good follow-up read.)

What happens next surprises some families. “Families do not all define inheritance the same way,” David said. “Some focus on property or financial resources. Others are especially concerned about clarity, family relationships, and reducing uncertainty for the people who will carry out their wishes.”

His fix is in the order of things. “Our approach is to make the conversation personal before making it procedural,” he said.

Sometimes the whole family shows up. On our October call, David described sitting down with four generations of one family, from a woman born in the Silent Generation all the way down to her great-grandchildren. “We had all of them in the living room just having one big conversation,” he said. “We make it fun and interesting, too. We just talk with each other. I tell them about me, my wife, and my kids.”

What Do You Want Your Family to Know?

Lisa White Burns, Founder and Financial Wellness Coach at Her Path, LLC, sees the weight on the other side of the table. “Often this conversation can be uncomfortable for those that are leaving the inheritance, especially women,” she said. “They worry about what is fair, feel guilty about how this should happen, and so much more.”

So she lowers the stakes before she asks anything. “I try to make sure that it's just a conversation, no final decision to be made, just thinking things through.” A meeting with no homework is an easier one to say yes to.

Then comes her question: “Have you had a conversation with your family about what you want them to know—not just what you want them to receive?”

“That usually changes the tone,” Lisa said. In her experience, people put it off because “they don't know where to start. And so by starting with just talking about it, I'm able to help them take that first step.”

When a client’s first step turns into decisions, an estate plan built with Trust & Will lives online and can be kept current as life changes, so the next family conversation doesn’t mean starting over.

How to Talk to Clients About Inheritance: Quick Answers

When should advisors bring up inheritance with clients?

Early, and on a schedule. For Matthew Veland, “Discussing inheritance is just part of my process,” with a dedicated meeting when a client first signs on and a check-in every year after. Matt Koppelman starts with the client's life goals, and “Estate planning usually comes up on its own that way.”

What if a client doesn't want to talk about inheritance?

Take the pressure off. Lisa White Burns tells clients “it's just a conversation, no final decision to be made, just thinking things through.” David Wright Jr. eases in the same way. “Our approach is to make the conversation personal before making it procedural,” he said.

Why do clients avoid the inheritance conversation?

Some worry about how it looks. “I think people see it like they don't want to seem greedy, like, what am I getting?” Al Faber said. Others are simply stuck at the start. In Lisa's experience, “they don't know where to start.”

What are good inheritance conversation starters for clients?

Start with the people. David Wright Jr. asks, “What do you want your legacy to be?” Matthew Veland asks clients “if they have a spooky estate planning story of their own.” The full set of six openers sits at the top of this article.

Be the Eight Percent

Every advisor on this panel opens a little differently, and every one of them is willing to say the first sentence. Bob put it best.

“Nobody really wants to talk about inheritance over Thanksgiving dinner or wait until a crisis forces the conversation. Sometimes the best thing a professional can do is just be the person willing to bring it up first.”

Borrow whichever opener sounds most like you and try it in your next review. No costume needed. That's how the 8% grows.

Want an easier icebreaker? Share Trust & Will's Death & Inheritance Report with clients and let the numbers start the conversation for you.

Interested in partnering with Trust & Will to support your own clients' estate planning needs? Learn more about how you can join over 20,000 financial advisors and firms who are delivering peace of mind to their clients by offering a comprehensive estate planning solution. Sign up for free today.

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