LEGACY FAMILY- A FRESH LEADERSHIP OFFERING
The greatest risk to your family's wealth isn't a bad investment.
It's a family that hasn't prepared.
Legacy Family helps successful families build the trust, communication, and governance that carry wealth — and what matters more than wealth — across generations.
70%
of wealth transfers fail by the third generation, and the cause is almost never the investments.
60%
of those failures trace to a breakdown of trust and communication within the family.
20+
years guiding leaders, teams, and families through their most important conversations.
The Problem
Every culture has a version of the proverb, because every culture has watched it happen. The first generation builds. The second generation manages. The third generation loses it — not because of taxes or markets, but because the family never learned to talk, trust, and decide together.
You have excellent advisors for the money: wealth managers, attorneys, CPAs, estate planners. But the estate plan only works if the family does. Legacy Family is the missing piece — a facilitated process that prepares the family, not just the assets.
“This is Meeting One. The goal is not resolution — it is trust.” The Legacy Family design principle
“Shirtsleeves to shirtsleeves in three generations.”
THE APPROACH
One retreat starts it. A generation sustains it.
Legacy Family works on two horizons: a proven retreat experience that builds trust fast, and a long-term legacy planning arc — grounded in the multigenerational research of Dr. Lee Hausner — that turns one good meeting into a family system that lasts.
Horizon One — The Legacy Family Retreat
A 3-day facilitated family retreat, preceded by confidential one-on-one interviews and assessments with every participant. Positive, structured, and safe — designed so the first family meeting builds trust instead of opening wounds.
• Confidential pre-retreat interviews & Working Genius assessments
• Custom-designed curriculum for your family, at a destination of your choosing
• Family & personal timelines, shared history, and legacy stories
• Trust-building frameworks: BRAVING & The Speed of Trust
• First governance conversations: vision, roles, and next steps
Horizon Two — The Legacy Arc
The retreat is Meeting One — not the finish line. Over months and years, we help your family build the structures that great families use to thrive for generations, drawing on Dr. Lee Hausner's Legacy Family framework.
• Grow all four family capitals — not just the financial one
• A rhythm of family meetings, councils & annual retreats
• Family vision, values & alignment statements that guide trustees
• Next-generation development, mentoring & financial parenting
• Philanthropy, shared traditions & conflict-resilient communication
Inside the Retreat
A deliberate three-step arc
Most family meetings fail because they start with the hardest topics. Ours are sequenced so the family earns the right to have the hard conversations.
Step 01 — Begin with the Positive
Gratitude, shared history, and the science of positive psychology open the room. Families rediscover what they admire in one another before anything else is asked of them.
Step 02 — Build Trust
Personal histories, vulnerability-based trust, and clear behavioral agreements (BRAVING, The Speed of Trust) create psychological safety strong enough to hold real conversations.
Step 03 — Grow Healthy Conflict Capacity
With trust banked, the family learns to disagree productively — naming tensions, practicing repair, and making first decisions about governance and the future.
THE LONG VIEW — DR. LEE HAUSNER'S FRAMEWORK
True family wealth is four capitals, not one
Families that endure invest deliberately in all four. Families that fail usually invested in only one.
Human Capital
The wellbeing, character, and productive purpose of every family member — each one finding meaningful work and a life of their own.
Financial Capital
The assets themselves — stewarded, governed, and understood by prepared inheritors rather than surprised ones.
Intellectual Capital
The family's knowledge, competence, and financial literacy — and how intentionally it is passed to the rising generation.
Social Capital
The family's connection to community — philanthropy, service, and shared purpose that give wealth its meaning.
PROVEN IN PRACTICE
From first conversation to family alignment
A multigenerational family enterprise — a founder-led operating business with significant family wealth — was referred to us by their wealth management team. The parents had done everything right on paper. What they didn't have was a family that had ever sat in one room and talked about it.
We conducted confidential interviews with every family member, designed a custom curriculum, and facilitated a 3-day retreat at a destination resort — then transitioned the family into an ongoing governance rhythm.
Trust first. Every generation heard one another's stories — some for the first time.
Shared language.The family now uses common frameworks for communication and conflict.
A path forward. Clear next steps for governance, roles, and the rising generation.
Advisors included. The family's wealth team stayed at the center of the plan.
OUR TEAM
Guided by experience. Grounded in research.
Craig Chong - Founder & Lead Facilitator
Craig has spent more than 20 years helping leaders, teams, and families navigate their most important transitions — serving 150+ businesses across Hawai‘i and the mainland. He brings the rare combination of executive-level facilitation and deep personal care to every family he serves.
• Professional Certified Coach (PCC) & Hudson Institute Master Coach
• Certified EOS Implementer® & Working Genius Facilitator
• Senior Birkman Consultant; NAVIX Exit Strategy Consultant
• M.A. Intercultural Studies in Leadership & M.A. Theology, Fuller Seminary
Linda Lindquist - Facilitator & Sr. Strategic Advisor
Founder & CEO of Courageous Thinking Inc., Linda spent 25 years guiding CEOs, entrepreneurs, and their teams through high-stakes change before turning her practice toward the work she now calls her most important: families. A world-champion offshore sailor who has raced on more than 100 crews, she came to family work through a simple conviction — the things that make a winning crew are the things that make a family endure: trust under pressure, honest communication, and a shared destination. Today she advises enterprising and multigenerational families, including some of America's most prominent, as they navigate wealth, transition, and legacy.
• Founder & CEO, Courageous Thinking Inc. (cgthink.com)
• Sr. Strategist & Trusted Advisor to enterprising families and their leaders
• 25 years facilitating leaders and teams through change & transition
• Speaker on navigating change, alignment & legacy
Dr. Lee Hausner, PhD — Sr. Advisor
One of the nation's foremost authorities on multigenerational family wealth, Dr. Hausner literally wrote the book on it — The Legacy Family — and has advised ultra-high-net-worth families worldwide for over three decades. Her research and frameworks anchor the long-term arc of every Legacy Family engagement.
• Author, Children of Paradise: Successful Parenting for Prosperous Families
• Co-author, The Legacy Family: The Definitive Guide to Creating a Successful Multigenerational Family
• Clinical psychologist; 17 years senior psychologist, Beverly Hills Unified School District
Sandy Chong — Facilitator & Client Experience
A former financial advisor who built a successful advisory practice (Series 6 & 7), Sandy speaks the language of wealth — but her true gift is reading the heart of a family. She and Craig have raised two daughters with deep values and a strong work ethic while anchoring their own extended, multigenerational family. Clients know her for an uncommon intuition and discernment about people and family dynamics, a grounding voice of prayer and blessing when families welcome it, and a warmth and hospitality that set the tone for every retreat.
• Former financial advisor; built a successful advising practice (Series 6 & 7)
• Certified Birkman Consultant & coach
• Gifted in discernment of people & family dynamics
• Hospitality & client care — the warmth behind every Legacy Family gathering
FOR ADVISORS & CENTERS OF INFLUENCE
Your clients' family dynamics are the biggest risk to the plan you built
Wealth advisors, attorneys, estate planners, and CPAs refer families to Legacy Family because it protects the plan — and deepens the relationship.
You stay at the center
We don't manage money, draft documents, or file returns. We prepare the family to receive the plan you built — and we keep you involved throughout.
Deepen client loyalty
Advisors who bring family preparation to the table become indispensable across generations — the single best predictor of retaining assets through a wealth transfer.
A proven, discreet process
Confidential interviews, professional facilitation, and complete discretion. Your client relationship is protected at every step.
QUESTIONS FAMILIES ASK
Is this therapy?
No. Legacy Family is professional facilitation, not counseling. Sessions are structured, positive, and forward-looking. Where deeper individual work is needed, we refer to appropriate professionals.
Our family isn't in conflict. Do we need this?
The best time to build trust and governance is before you need it. Families who wait until conflict — or a health event, sale, or estate transition — forces the conversation have far fewer options.
What happens before the retreat?
Craig conducts a confidential one-on-one interview and assessment with each participant. What's shared privately stays private — it shapes the design of the retreat without ever being attributed.
Where do retreats happen?
At a destination of your family's choosing — typically a resort setting away from home, where the family can be fully present together.
What does it cost?
Retreat engagements are custom-scoped and quoted after an initial conversation. Long-term Legacy Arc engagements are structured as annual partnerships.
Will our advisors be involved?
Yes, as much as your family wishes. Most engagements begin with a referral from a trusted advisor, and we design the process to strengthen — never bypass — those relationships.