“What Matters Most” Family Legacy Conversation Guide

Why This Conversation Matters

Most families never sit down to talk about what their wealth is actually for. They talk about numbers. Account balances, tax bills, the will. What gets left out is the harder and more important conversation: what the family values, what they want the next generation to understand, and how they want to be remembered.

This guide is built to open that conversation before you sit down with an advisor. It gives your family a shared starting point, so the meeting becomes a continuation of a conversation you have already started, not the beginning of one.

There are no right answers here. The goal is understanding, not agreement.

How to Use This Guide

Set aside uninterrupted time, ideally with the people who will be part of these decisions. Read each section together. Let each person answer in their own words before moving to the next. Some sections will be quick. Others may take more than one sitting. That is normal.

Write down what stands out. Bring your notes to your advisor conversation.

Section 1: Our Story and Values

• What is one story from our family's history that says something about who we are?
• What values were passed down to us, and which ones do we want to pass down?
• What has money meant in our family, historically? Security, opportunity, obligation, freedom?

Section 2: Wealth and Its Purpose

• What do we want our wealth to accomplish, beyond providing for basic needs?
• Are there causes, institutions, or people outside our immediate family we want to support?
• What would it mean for our wealth to outlive us in a meaningful way?

Section 3: Family Roles and Decisions

• Who in the family currently understands our full financial picture? Who should?
• If a decision needed to be made quickly, who would we want involved?
• Are there any assumptions about roles or responsibilities that have never actually been said out loud?

Section 4: Preparing the Next Generation

• What do we want the next generation to know before they inherit anything?
• What skills, habits, or experiences do we want to make sure they have?
• What are we most concerned about when it comes to passing on wealth?

Section 5: Wishes for Care and Legacy

• If a health event limited our ability to make decisions, what would we want to happen?
• What do we want people to say about us, and about our family, in the years after we are gone?
• Is there anything left unsaid that this conversation has brought up?

Bringing This to Your Advisor Conversation

Once your family has worked through these questions, the conversations that follow — estate plan review, gifting strategy, and charitable giving — become much more productive. Your advisor is not starting from a blank page. They are helping you build a plan around values your family has already named.