Conversations about money are rarely just about dollars. They’re about values, priorities, expectations—and sometimes, unspoken tension. That’s why many families, even financially successful ones, avoid them altogether.

According to a Merrill Lynch study, 66% of parents say they’d rather talk about their own death than their finances. Yet more than 70% of those same parents want their children to be prepared to manage family wealth responsibly.

At VestGen, we help clients bridge that gap. Because the best financial plans don’t just transfer wealth—they transfer wisdom. And that begins with conversation.

Why It’s So Hard to Talk About Money

For many families, the struggle starts with good intentions:

• “We don’t want to burden them.”
• “We want to avoid entitlement.”
• “We’re waiting for the right moment.”

But life rarely hands us the perfect time. And when no plan is shared, adult children often inherit complexity, confusion, and conflict—at the very moment they’re grieving.

Proactive communication can help:

• Prevent disputes between siblings
• Ensure your financial and legacy wishes are honored
• Build trust and capability across generations

It doesn’t have to be all-or-nothing. But it does need to begin.

Step One: Start with Why

Before sharing numbers, share your “why.”

• Why did you save the way you did?
• What are your hopes for how your children will use an inheritance?
• What lessons about money or responsibility are most important to you?

This reframes the conversation from “Here’s what we have” to “Here’s what we believe.”

At VestGen, we often facilitate this discussion with clients to help bridge financial data with family meaning.

Step Two: Choose the Right Format

Not every conversation needs to happen around the dinner table. In fact, some of the most productive conversations happen in smaller groups or over multiple sessions.

Consider:

• A series of one-on-one conversations with each child
• A facilitated family meeting with your advisor present
• A written legacy letter that complements formal estate documents

The goal is a format that promotes understanding, not anxiety.

Step Three: Share What Matters Most

You don’t have to disclose everything to have a productive conversation. But some topics can provide clarity and reduce confusion down the road:

• General structure of your estate plan (wills, trusts, powers of attorney)
• Who will serve in key roles (executor, trustee, healthcare proxy)
• Values around giving, philanthropy, or family business succession
• Any important wishes about property, heirlooms, or care responsibilities

We help clients prepare talking points, answer tough questions, and communicate clearly across generations.

Step Four: Educate Without Lecturing

One of the best ways to prepare heirs is to involve them.

That might include:

• Giving adult children visibility into certain financial decisions
• Inviting them to join you in conversations with your advisor
• Gifting small amounts during life to practice stewardship

Education doesn’t need to be formal. It needs to be consistent, respectful, and rooted in shared goals.

How VestGen Helps Families Communicate and Prepare

Legacy planning isn’t just about asset transfer—it’s about people. Our advisors help families:

• Facilitate intergenerational conversations
• Align estate planning documents with family dynamics
• Incorporate charitable and impact giving into family goals
• Prepare heirs to lead, not just inherit

We work with you to ensure your financial plan reflects both your technical goals and your emotional priorities.

A Legacy That Lasts Beyond the Balance Sheet

The most successful wealth transfers happen when heirs understand both the “how” and the “why.”

By starting the conversation now—and returning to it regularly—you create a path for trust, understanding, and long-term alignment.

If you’re unsure how to start this conversation with your family, we can help. Schedule a confidential conversation with a VestGen advisor to begin planning a legacy that lasts.