The Secret to Keeping Wealth in the Family: Talk to your kids about your money

Most families think the biggest risk to their wealth is the market. It isn’t. Decades of working with families in the Berkshires, Massachusetts, and beyond has taught me something surprising: the greatest threat to multigenerational wealth isn’t market swings, taxes, or even a poorly drafted estate document. It’s the silence created when parents don’t talk to their kids about the money they’re going to inherit.

Silence often settles in quietly, and usually grows from uncertainty, not deliberate secrecy. Maybe your spouse handled all the financial conversations during your marriage, or you were raised to believe money was a private matter not meant to be discussed. Or maybe you worry that talking openly about the wealth your kids will inherit will create expectations – or even dependence.

Many families benefit from working with a financial planning team experienced in multigenerational wealth conversations. At Berkshire Money Management, I help parents prepare for those discussions with clarity and confidence.

I hear concerns like these from clients and friends all the time:

“I worked so hard… I don’t want my kids taking their inheritance for granted.”
“I’m afraid talking about money with my children will change our relationship.”
“I don’t even know how to begin a financial conversation.”

These are real fears and, whether you realize it or not, money can be an incredibly emotional topic. Your wealth is connected to your values, your work ethic, the sacrifices you made, and the hopes you hold for your children and grandchildren. And opening up—especially if you’re navigating these decisions on your own—can feel like stepping into a lion’s den. But the alternative is far worse: without communication, even the most well-built estate plan can be torn apart.

The good news is that communicating with your family about your wealth doesn’t require a lion tamer. It doesn’t need to be formal or polished, either. You simply need to begin.

What happens when families don’t talk about money

Years ago, I worked with a woman, let’s call her Sherri, who had saved diligently for decades with her late husband. They lived modestly, and their children assumed they had “enough” but not much more. When their oldest son and his family found themselves struggling with housing costs, Sherri didn’t hesitate to buy them a home closer to the city with the intention of creating stability for her grandchildren and supporting her son’s career.

But because Sherri and her family had never discussed their values around saving, work, or long-term planning, the gift landed without context. When the housing market surged, her son and his wife sold the house, moved to a more rural area, reduced their work hours, and began living off the proceeds. Sherri was stunned. This was not the future she and her late husband imagined—not for their child, and certainly not for their grandchildren. Years later, Sherri still feels hurt, but hasn’t directly addressed the issue with her son. And because Sherri hasn’t discussed her wealth with any of her four children, her son and his siblings are set to inherit the rest of her savings without any idea how hard she and their father worked for that money or what they hoped it would mean for them.

The problem in Sherri’s story isn’t the gift. The problem is the absence of communication about her values, intentions, and expectations. This is a pattern I see often: when money shows up without guidance, children fill in the gaps themselves, and those decisions rarely align with the parents’ wishes.

Focus on meaning, not account balances

Many people avoid discussing inheritance because they assume they have to share exact numbers and details about their personal wealth. In reality, what your adult children need most from these conversations is clarity about:

• The values behind your decisions
• The purpose of your wealth
• What you hope the money will (and will not) do
• Your expectations for how decisions should be made in the future

Giving your kids clarity about your wealth is especially important if you’re widowed or divorced, or if your spouse was the one who previously carried these conversations. The financial story now needs your voice, not because you owe your family details, but because they need direction.

Starting a financial conversation with your kids can feel daunting, but one sentence can open the door: “I’d like to talk about what matters to me, and what I hope this money accomplishes for our family.” And remember, you don’t need to cover everything in one day. The most important thing is to start.

Frequent financial conversations help families thrive

When families talk about their money, everything else becomes easier:

• Decisions about your health and estate feel less mysterious
• Children feel informed, not entitled
• Grandchildren benefit from your values, not just your assets
• The family understands the why behind your choices
• Family squabbles are stopped before they start

In our Rock-Solid Family Wealth Plan, we say that communication is the “mortar” that holds the whole structure together. Without it, even well-built plans can crumble under the weight of assumptions.

3 Core topics for family wealth conversations

The families that are best at communicating about their wealth tend to cover three core topics, each crucial for keeping wealth intact across generations:

1. The story of how your wealth was built

Telling your children the story of how you built your wealth and why helps the next generation understand the values behind your assets such as discipline, sacrifice, and long-term thinking, not just the assets themselves. Without this context, your wealth is just money; easy come, easy go.

2. What your wealth is intended to support

Your children can’t honor your wishes if they don’t know them. Sherri wasn’t clear with her son that she wanted to provide stability for her grandkids – not fund his unemployment. To avoid conflict, make sure the next generation understands what you want your money to be used for, whether that’s education, stable housing, togetherness, community impact, or something else entirely.

3. What you expect from them after you’re gone

Your estate plan will include plenty of legal instructions for your wealth, but do your kids know your wishes for their future? Consider the following:

• Should decisions be made jointly?
• Should inheritances support work or replace it?
• Should assets be protected from potential spouses, creditors, or poor decisions?
• Should grandchildren be encouraged to pursue education, certain milestones, or charitable involvement?

Your ultimate goal in having these conversations is to translate your intentions into something your family can follow when you’re no longer here to guide them.

How to start talking to your kids about inheritance

Most people imagine that talking to their family about money requires a formal meeting or a detailed explanation of their entire financial picture. It doesn’t. In fact, the best conversations often start in much smaller, more natural ways.

You might begin with a story about how you learned to save, or a decision you made early in your life that shaped how you think about money. You might bring up a charitable organization you support and explain why it matters to you. Some parents even start by giving a small gift of stock, not for the financial impact, but to spark a discussion about long-term planning and responsibility.

The goal of your first conversation isn’t to cover everything at once; it’s simply to make the topic familiar. Many clients tell me that once they say the first sentence, the rest becomes easier. The fear subsides, and the conversation becomes more natural than they expected. If you want some structure, our Quick-Start Guide to Family Meetings offers prompts and conversation starters that help families open the door to these discussions without making them feel too formal or overly pressured.

The most important part of your first family wealth conversation isn’t the format – it’s that you begin. Over time, these conversations create clarity, reduce anxiety, and give your family a shared understanding of what your wealth is meant to support.

Who can help you address your finances with your family

You don’t have to face these conversations alone. A financial advisor who understands estate planning—and the challenges that come with it—can help you translate your wishes into a clear, workable plan and communicate it to your family. Berkshire Money Management has been guiding families through tough financial conversations for decades and I can tell you, when it comes to family dynamics, very little surprises me anymore. Together, the right team can help your family stay aligned, informed, and protected.

Your estate attorney also plays an important role in these conversations about your wealth while putting the right legal protections in place so your intentions are carried out the way you envision. If you’re working with an estate attorney, it doesn’t hurt to ask if they’d be willing to host a family meeting with you and your children to go over all the important points.

Don’t wait – start the conversation with your family now

Whether you’re 55 or 85, tomorrow is never guaranteed. When you pass away, your estate plan will outline the legal distribution of your assets, but communicating with your family today is what fills in the human details the documents cannot. When parents avoid discussing their wealth with their children, several things tend to follow:

• Children receive assets they don’t know how to manage.
• Siblings disagree about “what Mom would have wanted.”
• Probate becomes longer, more expensive, and more emotional.
• Tax opportunities are missed.
• Wealth gets divided in ways that don’t reflect your true wishes.
• Families become divided, sometimes permanently.

I’ve seen families torn apart simply because no one knew the parents’ intentions. I’ve also seen families move through difficult transitions smoothly because expectations were clear long before anyone needed to act on them.

Frequently Asked Questions

1. When is the right time to start talking to my adult children about inheritance?

The best time is before a crisis, major gift, or estate event. A simple, low-pressure conversation—such as sharing your values, hopes, and intentions—builds understanding long before money ever changes hands. The earlier these conversations begin, the more natural and helpful they become.

2. Do I have to share exact numbers when I talk to my family about my wealth?

No. Most families don’t need or want a full financial disclosure. What your children need is clarity about things like:

• What you want your wealth to support
• What it should not support
• How decisions should be made in the future

3. What should we talk about in our first family wealth conversation?

Start small and personal. Useful first-conversation topics include:

• How you built your wealth and what shaped your financial values
• What you hope your money accomplishes for your children or grandchildren
• How you think about work, saving, and responsibility
• Why certain causes or gifts matter to you
  
  

4. How do I prevent conflict between my children after I’m gone?

Clear expectations are the strongest antidote to future conflict. Families avoid the biggest disputes when they:

• Communicate their intentions while they’re still alive
• Explain the reasoning behind major decisions
• Document those intentions with an estate attorney
• Use the right structures—trusts, beneficiary designations, or joint decision-making guidelines—to reduce ambiguity
  
  

5. Who can help me lead inheritance conversations with my family?

A seasoned financial advisor or estate planning attorney can guide the conversation, help translate your wishes into a clear plan, and even host a family meeting if needed. Professionals like the team at Berkshire Money Management who understand both estate strategy and family dynamics can make inheritance discussions easier, more productive, and less emotional.

Plan your first family meeting

Our Quick-Start Guide to Family Meetings is designed to help you share your values and wishes with your family efficiently and without drama.

Some of the names and details in this article have been modified to protect the privacy of the subjects.