With Thanksgiving just days away, many BSW clients will gather – whether with family, close friends, or in quiet reflection – to share a meal, reconnect, give back, or simply enjoy a day in good company. This season of turkey dinners, pumpkin pie, and shared laughter reminds us that true abundance extends beyond financial success. It lives in the connections around the table, the stories shared across generations, and the sense of belonging that brings us together.
Moments like these invite us to reflect on how what we create today can shape what lies ahead. When we pause to consider the conversations we have, the lessons we pass on, and the example we set, we often become more intentional about the impact we make and the future we build. In this season lies an opportunity to inspire the next generation with the confidence, knowledge, and resilience to carry our vision forward and manage our legacy with intention.
You may wonder: how do you prepare the next generation not only to be financially savvy, but also with the maturity and perspective to navigate the future? We asked our advisors Julie Martinez, Eric Davis, and Ben Weaver for thoughtful guidance to help you approach this topic with confidence. While every family’s story is unique, certain factors can make these discussions more meaningful. Our advisors share practical tips, helping you set the stage for intentional dialogue this holiday season or when the moment feels right for your family.
Timing and Setting Matter
For family conversations to be truly meaningful, thoughtful preparation around timing and place can lay the groundwork for openness and trust. As you prepare, consider moments and settings that foster focus, connection, and understanding. Here are a few things to keep in mind:
1) Start early and revisit often: The ideal time to involve the next generation in wealth conversations depends less on age and more on readiness. As Eric notes, “If the next generation shows interest or proficiency, it’s wise to begin early.” Try to introduce key financial concepts gradually and in an age-appropriate way while avoiding overly technical or number-heavy discussions. Julie emphasizes that these conversations often are most effective when they can unfold over time, rather than tackling them all at once.
2) Pick a private, comfortable space: Ensure the setting is free from distractions and that everyone feels safe to speak openly. “Wealth management isn’t just about giving instructions,” says Julie. “It’s about creating space for questions, curiosity, and open dialogue.”
3) Be clear and inclusive: Explain why the conversation matters and invite input from the younger generation. As Julie notes, encouraging participants to explore their roles, ask questions, and provide their perspective can help build confidence and a sense of ownership.
Lead with Meaning, Not Numbers
Starting the conversation with qualitative aspects such as values and goals before sharing financial details can help the next generation connect wealth to meaning and purpose, rather than viewing it as just something to receive.
One common concern, as Ben notes, is that talking about wealth too early might dampen a child’s drive to chart their own path. He recommends letting younger family members grow into their roles over time, guiding early conversations around opportunity, responsibility, and shared values, and carefully matching timing with readiness.
Still, the idea of preparing heirs is often misunderstood. We believe that wealth stewardship should be less about maintaining control, imposing personal values, or setting rigid expectations, and more about empowering the next generation to make thoughtful, informed choices. As Julie puts it, “The goal is to equip the next generation with the tools and knowledge to manage wealth responsibly, creating space for them to explore their own understanding of wealth, and encouraging decision-making grounded in clarity and purpose.”
Starting the Conversation: Two Approaches
The best way to approach family wealth conversations may vary from family to family. Some may prefer conversations that happen naturally around the dinner table while others may opt for a more structured format with specific topics and guided questions. Whether you choose a casual or more intentional approach, each offers an opportunity to connect, inspire, and empower. Here are a few ideas to help get the conversation started.
Conversation topics for naturally flowing discussions
The following topics can guide conversations that feel natural and engaging, moving from reflecting on the past to future goals and ways to make an impact. Try these:
- Favorite family memories or stories about past generations
- Lessons from past decisions
- Unexpected lessons learned from mistakes or challenges
- Plans for the year ahead
- Goals, dreams, and ambitions
- Ways to give back to the community
For intentional, guided conversations:
These topics are designed to spark meaningful dialog and provide a structured way to explore values, decision-making, family legacy, and charitable intentions. You may start the conversation with the following:
Personal Values & Life Direction
- I’d love to hear about your plans and goals in life – where do you see yourself in the next 3-5 years?
- What does success mean to you?
Financial Decision-Making
- If you had money to manage right now, how would you use it?
- How do you approach balancing spending, saving, and giving, knowing that managing money involves trade-offs?
- Are there lessons from past financial mistakes that have shaped your relationship with money?
Family Wealth & Legacy
- What do you hope our family’s resources will help us achieve together?
- Are there ways you would want to be involved in managing our family’s resources?
Philanthropy & Impact
- If our family could support any cause, what would make the biggest impact in your view?
- Are there causes or issues that are particularly important to you?
Having conversation topics can be helpful, but we believe it is equally important to remain flexible and attentive to how the younger generation responds. Active listening can create space for reflection, encourage openness, and allow participants to be honest and ask questions. If you notice the younger generation is not quite ready to dive deep, we recommend you don’t force the conversation. Let it unfold naturally, building trust and encouraging engagement over time.
Whether casual or intentional, we hope that these tips and prompts spark meaningful conversations around the table – amid turkey dinners, pumpkin pies, and laughter – and create connection in your family.
Wishing you a wonderful Thanksgiving!
The Financial Planning Team
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