Q/A
Legacy Conversations That Transform Families
Legacy planning isn’t just about documents, strategies, or numbers—it’s about people.
Every family carries a story shaped by values, relationships, and decisions that ripple across generations. Yet too often, those conversations never happen. Misalignment grows. Assumptions replace clarity. And the very wealth meant to help a family can quietly create tension instead.
This conversation brings together experienced advisors and practitioners who have spent years walking families through these exact challenges. From navigating generational differences to addressing conflict, faith, communication, and leadership—these insights go beyond theory and into real-life application.
What emerges is simple but powerful:
Families don’t break down because of a lack of planning.
They struggle because of a lack of alignment, communication, and intentionality.
Whether you’re an advisor, a family leader, or someone seeking to steward your resources well, this is a starting point for deeper conversations—ones that lead to clarity, unity, and a legacy that truly lasts.
Choose Your Legacy Pathway
Designed for Every Role of Influence
Getting Families to Care Beyond “Documents” (5:23)
The profound role of love in family legacy planning, advocating for open communication rooted in affection. It highlights that true legacy extends beyond financial wealth to encompass talents, relationships, and values. The speaker stresses the importance of perspective, prayer, and proactive communication for couples and families to ensure a harmonious and impactful transfer of assets.
Choosing the Next Generation Leader (5:23)
The critical role of effective communication in family meetings, particularly when appointing an estate executor or business leader. It emphasizes selecting the most capable individual, whether family or external, based on organizational and emotional strengths. The discussion highlights how clear priorities and the complexity of the business dictate succession planning for long-term success.
Conflict Blocking Progress - Family Legacy By Design (2:50)
The complexities of family legacy planning, featuring discussions on navigating conflict and wealth transfer. Three men share insights on fostering unity and addressing emotional challenges within families. The importance of personal responsibility and professional counseling for unresolved issues is highlighted, emphasizing proactive communication for a strong family foundation.
Family Misalignment - Conflict in Values (6:09)
Navigating family dynamics and generational value conflicts. It highlights the importance of understanding children's perspectives during disagreements and offers strategies for fostering alignment. Experts discuss how to guide children through decision-making, emphasizing genuine support and the journey over the outcome, ultimately aiming for stronger family relationships.
Choose Your Legacy Pathway
Designed for Every Role of Influence
Disclosing Inheritance to Kids (3:49)
Explore the complexities of disclosing inheritance amounts to children with Tom Conway of Family Legacy by Design. Learn why transparency can foster trust and improve family communication, even when charitable giving alters the final inheritance. Discover how unprepared heirs can be negatively impacted by undisclosed wealth and the importance of initiating these sensitive conversations early.
Pitfalls of Legacy Planning (4:12)
This insightful discussion features Tom Conway, Randy Fairfax, and Jerry Black exploring the nuances of legacy planning. They emphasize that practical experience and continuous learning are key, rather than assuming expert knowledge. The speakers advocate for collaboration with family advisors, highlighting the value of understanding family dynamics and history to provide effective counsel. This video aims to demystify legacy planning for everyone.
Misalignment Between Generations (6:48)
This video explores the critical aspects of family legacy and wealth management, highlighting the common pitfalls of generational misalignment. Experts Tom Conway, Randy Fairfax, and Jerry Black discuss how differing perspectives between parents and their children can derail even substantial estate planning efforts. They emphasize the importance of open communication and involving the next generation in decision-making to ensure a cohesive and successful transfer of wealth.
Someone who feels called to legacy coaching (5:40)
This video explores building trust and rapport with clients, regardless of their faith. The speaker emphasizes understanding individual stories and the universal human desires for family, security, and generosity. By focusing on core human values and presenting oneself as knowledgeable, professionals can foster strong relationships and facilitate meaningful conversations about life's important aspects, including finances and legacy.
Choose Your Legacy Pathway
Designed for Every Role of Influence
Clients Without Faith Foundation (3:04)
This video explores building trust and rapport with clients, regardless of their faith. The speaker emphasizes understanding individual stories and the universal human desires for family, security, and generosity. By focusing on core human values and presenting oneself as knowledgeable, professionals can foster strong relationships and facilitate meaningful conversations about life's important aspects, including finances and legacy.
Business Model - Making It Work Financially (11:46)
This video explores the intersection of financial success and personal fulfillment in a vocation, particularly in financial advisory roles. It emphasizes the importance of a genuine calling, a desire to help families, and the development of both technical and interpersonal skills. The discussion highlights common pitfalls in client engagement and advocates for leveraging individual strengths through collaboration to effectively steward resources and contribute positively.
Legacy Events in Action
Endorsements
Discover how coaches and financial advisors are being equipped through Family Legacy By Design live workshops to guide clients in building meaningful, multi-generational legacies.
“Tom has the heart of a shepherd. He doesn’t just advise families on finances—he walks with them, listens to their stories, and helps them steward everything God has entrusted to them.”
Building a Comprehensive Legacy Library
Over the next 24 months, Family Legacy by Design is expanding into a full learning ecosystem — including books, certification programs, digital masterclasses, and church-based campaigns designed to serve families and those who guide them.