When was the last time your family talked openly—not about who gets what, but about what it all means?

Picture this: It’s Thanksgiving evening. The dishes are cleared, the kids are playing cards in the living room, and you’re sitting at the table with your adult children. Someone mentions a friend whose family was torn apart after their father passed – siblings who haven’t spoken in two years, all because no one knew what Dad actually wanted.

Your daughter looks at you and asks, half-joking: “So…do we know what you want?”

The table goes quiet. You’ve thought about this moment dozens of times, but somehow the words never come. Your son changes the subject. The moment passes.

Sound familiar?

The Conversation Everyone Avoids—And Why That’s Dangerous

Here’s a statistic that should alarm every parent: 70% of wealth transfers fail by the second generation—not because of poor investments, aggressive taxes, or bad timing, but because families never talked about what the wealth was for (Forbes, 2011)

The money was there. The estate plan was filed. But the meaning was lost.

Even more striking: when researchers ask why families don’t discuss wealth and legacy, two contradictory fears emerge:

• Parents worry that talking about money will make their children feel entitled, lazy, or change how they view the relationship
• Adult children worry that asking questions will make them seem greedy, impatient, or disrespectful

So both generations stay silent—each protecting the other from a conversation neither wants to start. Meanwhile, the very thing they’re trying to protect—family unity—becomes more fragile with every passing year.

The Family Recipe Metaphor

Think about your grandmother’s signature dish—the one everyone requests at holidays. Now imagine she never wrote down the recipe. Never showed anyone how to make it. Just kept the ingredients “somewhere in the pantry” and assumed someone would figure it out.

When she’s gone, what happens? The ingredients are still there, but nobody knows the proportions, the timing, the technique, the secret that made it special. Someone tries to recreate it and fails. Arguments start about whether it had cinnamon or cardamom. Eventually, people stop trying—and a piece of family identity disappears.

Your legacy is that recipe.

The wealth you’ve built is just ingredients. Without context, instruction, and shared understanding, it can’t nourish the next generation the way you intended. Talking about legacy isn’t about control or disclosure—it’s about ensuring your family knows how to carry forward your values with purpose.

“The greatest use of life is to spend it for something that will outlast it.” — William James

What Makes This So Hard? The Hidden Psychology

Before we get to how to have this conversation, let’s acknowledge why it feels nearly impossible.

For Parents: 

• Fear of appearing controlling or manipulative
• Worry about creating sibling rivalry or competition
• Anxiety that sharing “too much” will reduce children’s motivation
• Uncertainty about timing: Is it too early? Are they mature enough?
• The vulnerability of admitting mortality

For Adult Children: 

• Discomfort appearing interested in inheritance
• Fear of seeming like they’re “waiting” for parents to die
• Uncertainty about whether it’s “their place” to ask
• Generational taboos: “We just don’t talk about that in our family”

Here’s what we’ve learned after decades of facilitating these conversations: The discomfort you feel before the conversation is almost always worse than the conversation itself. And the relief families feel afterward—the clarity, the closeness, the shared purpose—is transformative.

Sarah’s Story: When Silence Became Crisis

Sarah was 54 when her mother died unexpectedly. She and her two brothers had never discussed finances with their parents—it wasn’t that kind of family. When they opened the estate documents, they discovered:

• Their mother had left the family home to Sarah (the only daughter) assuming she’d want to preserve it
• She’d left equal cash distributions to the brothers
• But the home represented 60% of the estate’s value

The brothers felt slighted. Sarah felt burdened—she didn’t want the house and couldn’t afford the upkeep. What their mother intended as a gift became the source of a family fracture that took years to heal.

“If she’d just told us while she was alive,” Sarah said later, “we could have talked through what made sense. Instead, we spent two years fighting over what we thought she meant.”

The lesson? Silence doesn’t protect anyone—it just postpones the pain.

The Seven Steps to a Meaningful Family Money Conversation

1. Clarify Your “Why” Before You Speak

Most people jump straight to logistics: “I want to tell them about the trust structure” or “They need to know where the documents are.” That’s putting the cart before the horse.

Start here instead…

Ask yourself:

• What life experiences shaped how I think about money?
• What do I hope this wealth accomplishes for my family after I’m gone?
• What mistakes do I want to help them avoid?
• What opportunities do I want to create?
• If I had only five minutes to share what I’ve learned about wealth, what would I say?

Write down your answers. You’re not creating a speech—you’re finding your truth. That authenticity is what makes the conversation meaningful rather than transactional.

Example opening: “I grew up with very little, and that shaped how I’ve approached every financial decision. I want you to understand not just what we’ve built, but why—and what I hope it means for your lives and your children’s lives.”

2. Choose the Right Setting (And Yes, It Really Matters)

Announcing “We need to talk about the estate” over Thanksgiving turkey is like proposing marriage in a crowded airport—technically possible, but terrible timing.

Instead, try this: 

• Schedule a specific time: “Saturday morning after breakfast, let’s take an hour together”
• Choose a comfortable, private space: a quiet room, a walk together, a fireside chat after the chaos has settled
• Eliminate distractions: no phones, no TV in the background, no interruptions
• Keep the group manageable: start with immediate family, expand later if needed

Gatewood tip: Some families find it easier to have this conversation away from the family home—perhaps during a weekend retreat or a quiet dinner out. The change of scenery can make difficult topics feel more approachable.

3. Set Expectations Beforehand (Eliminate the Ambush Factor)

Nobody performs well under surprise. Give your family the gift of preparation.

A week before, say something like:

“I’ve been thinking about our family’s future—not just finances, but our values and the legacy we’re building together. I’d love to spend some time this holiday talking about what matters most to us and how we want to care for each other. No pressure, no big reveals—just a conversation I think is overdue. Can we set aside Saturday morning?”

This framing:

• Reduces anxiety by removing mystery
• Positions the talk as collaborative, not dictatorial
• Focuses on values and relationships, not just money
• Gives everyone time to mentally prepare

4. Start With Gratitude, Not Numbers

The biggest mistake people make? Opening with logistics.

“So, we have three accounts, the house is paid off, and here’s who gets what…”

STOP. You’ve just turned a relationship conversation into a business meeting.

Instead, begin here: 

“I want to start b saying thank you. Thank you for being the people you’ve become, for the support you’ve given us, for making our family what it is. Everything we’ve built has been with you in mind—not just to leave you something, but to give you options, security, and the ability to make a difference in the world. That’s what this conversation is really about.”

Feel the difference? You’ve just created connection before content. That’s the foundation for everything that follows.

5. Focus on Purpose and Values First (The “Why” Before the “What”)

Here’s a question that will transform your conversation:

“What do you think I value most about money?”

Let them answer. You might be surprised—or concerned—by what they say. Their perception reveals what you’ve actually communicated through your actions over the years, which may differ from your intentions.

Then share your truth:

• The life lessons that shaped your relationship with money
• The mistakes you made that you want to help them avoid
• The values you hope will guide their decisions
• The causes or principles you want your wealth to serve
• The vision you have for how this wealth creates opportunity (not entitlement)

Share a defining story: “When I was 28, I made a terrible investment that cost us nearly everything we’d saved. I learned that wealth isn’t about taking big swings—it’s about consistent, purposeful decisions. That’s why we’ve always prioritized…”

Stories stick. Principles delivered through narrative create lasting impact.

6. Invite Questions and Listen Without Judgment (This Is the Hardest Part)

After you’ve shared your perspective, pause. Take a breath. And then ask:

“What questions do you have? What concerns? What would you like to understand better?”

Then do the hardest thing: be quiet and listen.

Your children might ask uncomfortable questions:

• “Why did you structure it this way?”
• “What if we disagree with your choices?”
• “Can we talk about changing X?”

Resist the urge to defend or explain immediately. Instead, try:

“That’s a fair question. Help me understand what you’re thinking.”

Remember: Questions aren’t challenges—they’re engagement. If your family is asking, it means they care. That’s exactly what you want.

Warning sign to watch for: If your adult children say “whatever you think is best” and clearly want to end the conversation, dig deeper. Avoidance masquerading as respect is still avoidance.

7. Create a Follow-Up Plan (Don’t Let This Be a One-Time Event)

End the conversation with specific next steps:

“This was really valuable. I’d like us to revisit this annually—maybe every holiday season. In the meantime, here’s what I’m committing to:

• Get our estate documents to you by [date]
• Schedule a meeting with our Gatewood advisors so you can meet them
• Update our beneficiary designations to reflect what we discussed

What would be helpful for you?”

Make it a ritual, not a reckoning. Annual check-ins normalize the conversation, reduce anxiety, and allow the dialogue to evolve as circumstances change.

The Questions That Change Everything

Five Questions to Ask Yourself Before the Conversation

1. What values or life lessons do I want my wealth to represent? (Not: what assets do I have)

2. Who in my family needs to better understand our financial plans—and why? (Consider: the responsible child, the struggling child, the son-in-law who never asks questions)

3. What do I want my children or heirs to feel—not just know—after this discussion? (Secure? Empowered? Prepared? Grateful? Connected?)

4. Are my estate, tax, and charitable plans aligned with the purpose I just defined? (Often, we find they’re not—and that’s okay; that’s what advisors are for)

5. How do I want my family to remember the way we handled this conversation? (This becomes part of your legacy too)

Questions to Ask Your Family During the Conversation

These questions turn monologue into dialogue:

2. “What do you think our family’s greatest strengths are?” (Establishes positive foundation)
3. “What causes or goals matter most to you personally?” (Reveals their values, shows you care about their vision)
4. “How can we use what we’ve built to help others—or to help each other?” (Reframes wealth as tool, not trophy)
5. “What worries you most about the future, financially or otherwise?” (Surfaces fears you can address together)
6. “How do you define a meaningful legacy?” (The most important question—their answer tells you everything)

Best Practices That Make It Work

Keep it brief: Ninety minutes maximum for the first conversation. You’re opening a door, not walking through the entire house in one day.

Keep it warm: Share a meal together first. Breaking bread creates connection that makes difficult conversations easier. 

Keep it ongoing: Say explicitly: “This is the first of many conversations.” Removes pressure to cover everything perfectly.

Keep it balanced: Don’t dominate. Aim for 50/50 talk time—half you sharing, half them responding.

Keep it guided: Consider inviting your Gatewood advisor to facilitate. A neutral, experienced third party can help navigate tension and ensure everyone feels heard.

The Holiday Connection: Why Now Matters

The holidays aren’t just convenient for family gatherings—they’re thematically perfect for this conversation.

This is the season of:

• Gratitude: expressing what we appreciate about each other
• Generosity: giving gifts that show care and foresight
• Reflection: looking back on the year and considering what’s ahead
• Tradition: honoring what we’ve received and deciding what we’ll pass forward

Your family legacy conversation isn’t separate from these themes—it’s the deepest expression of them.

By having this talk during the holidays, you’re giving your family the greatest gift possible: clarity where there was confusion, purpose where there was uncertainty, and connection where there might have been distance.

What If It Goes Wrong?

Let’s be honest: not every family conversation goes smoothly. What if someone gets defensive? What if siblings disagree? What if old resentments surface?

First, know this: Conflict that surfaces during the conversation is infinitely better than conflict that erupts after you’re gone. At least now you’re present to clarify, mediate, and adjust.

Second, remember: Perfect is the enemy of good. A slightly awkward conversation is still 100 times better than no conversation at all.

Third, get help if you need it: Gatewood advisors have facilitated hundreds of family legacy meetings. We know how to:

• Navigate different personality types and family dynamics
• Mediate when opinions diverge
• Explain complex financial structures in accessible language
• Keep conversations productive when emotions run high
• Create action plans that satisfy everyone’s concerns

You don’t have to do this alone.

How Gatewood Can Help

At Gatewood Wealth Solutions, we believe true legacy planning is about more than transferring assets—it’s about transferring wisdom, values, and purpose across generations.

Through our Firm-to-Family™ approach, we provide:

Structured Family Legacy Meetings

• Professionally facilitated conversations that keep everyone focused and heard
• Neutral third-party guidance that reduces family tension
• Clear documentation of decisions and next steps

Multigenerational Wealth Planning

• Integration of estate, tax, investment, and insurance strategies
• Education for the next generation on managing wealth responsibly
• Ongoing support as family circumstances evolve

Values-Based Planning 

• We start with your “why,” not your “what”
• Charitable giving strategies that align with your family’s passions
• Customized solutions, never cookie-cutter products

Continuity and Confidence

• Our multigenerational advisor team ensures someone will always be here for your family
• Real-time visibility into your complete financial picture through our integrated technology
• Dynamic planning that adapts to life’s key moments

We keep your priorities the priority—this year, next year, and for decades to come.

Your Next Step

This holiday season, give your family the conversation they need—even if they don’t know they need it yet.

Start small if you must. You don’t need to cover everything in one sitting. But start.

Because the alternative—leaving your family to guess what you meant, what you wanted, what mattered to you—isn’t protection. It’s a burden no one should carry.

The greatest gift isn’t what you leave behind. It’s the clarity with which you leave it.

Ready to start the conversation?

Schedule a Legacy Planning Conversation with Gatewood Wealth Solutions. We’ll help you prepare, facilitate the discussion if you’d like, and create a comprehensive plan that honors your values and preserves your family’s future.

Important Disclosures:

The opinions voiced in this material are for general information only and are not intended to provide specific advice or recommendations for any individual.

This information is not intended to be a substitute for specific individualized tax or legal advice. We suggest that you discuss your specific situation with a qualified tax or legal advisor.

Sources
Carolyn Rosenblatt, Wealth Transfers: How To Reverse The 70% Failure Rate, Forbes, December 9, 2011. Read Article