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The Emotional Foundation
Before the strategies and structures, multi-generational wealth starts with intention. This section explores what's driving you, what you're most concerned about, and what legacy you actually want to build.
When you think about passing your wealth to the next generation, what is your greatest concern?
Diminish work ethic or personal ambition
Cause conflict or division among my children
Lost to poor decisions divorce or creditors
They will not understand the values and stories behind the wealth
Not concerned - believe they are fully prepared
Which statement best describes your current approach to preparing your heirs for the wealth they will inherit?
Keep financial details private until after I am gone
Want to start preparing them but do not know how without creating entitlement
Actively teaching them but worry the lessons will not stick after I am gone
Have a structured ongoing process for preparing the next generation
What is your primary goal in building and transferring multi-generational wealth?
Financial security and a comfortable lifestyle
Opportunities for education entrepreneurship and personal growth
A tool to keep the family connected and working together for generations
A platform for significant philanthropic impact in the world
What is your marital status?
Do you have children?
Do you own a business?
Yes - I am a sole owner with no business partners
Yes - I have one or more business partners
No - I do not own a business
Intent vs. Reality & The 100-Year Vision
Most families say they want their wealth to last for generations — but few have translated that wish into a shared vision the next generation actually understands. This section measures the gap between intention and reality.
Do you have a clear, written vision for what you want your family's wealth to accomplish 100 years from now - beyond your own lifetime and your children's?
Wealth has grown significantly and is supporting my great-grandchildren
Family still gathers knows our shared history and supports one another
Both the wealth and the family connection are thriving and intertwined
Have not thought about a 100-year vision
How important is it to you that your wealth is managed collaboratively across generations, rather than each generation handling its share independently?
Extremely important - it is a core goal of my planning
Somewhat important but expect they will mostly go their separate ways
Not important - prefer to divide everything cleanly so they do not have to work together
Does your family currently make any significant financial or investment decisions together, as a multi-generational group?
Yes - have a structured family bank or shared philanthropy fund they manage
Partially - discuss decisions but I still make the final call
No - they manage their own money separately
How confident are you that your heirs have the skills, knowledge, and judgment to manage significant wealth responsibly?
1 - Not confident at all
2
3
4
5 - Extremely confident
Communication & Trust
Study after study points to the same cause when inherited wealth disappears: not bad investments or taxes, but a breakdown in communication and trust between generations. This section looks at how your family talks about money.
Fully open - my heirs know what exists and the thinking behind it Somewhat open - they know the broad strokes but not the details Limited - I share very little; they will learn most of it later Closed - we do not discuss family wealth
Regular structured family meetings with full transparency
Discuss general concepts but keep specific numbers and legal details private
Rarely discuss - they will find out the details when the time comes
Have not discussed it at all
Do you understand the different communication styles within your family and how they affect financial conversations?
Yes - formal assessments and understand how to adapt communication for each other
General sense of personalities but nothing formal
No - communicate the way we always have
Does your family have a healthy, established process for resolving conflict - especially conflict involving money or fairness?
Pre-agreed process for resolving disputes respectfully
Talk it out though it can sometimes get heated or emotional
Avoid conflict and let the issue simmer
I make the final decision to end the disagreement
Do your heirs have a genuine voice in family financial discussions - the chance to be heard on decisions, not just informed of them?
Yes - input is actively encouraged and carries real weight
Can ask questions but they know I have the final say
No - questioning my financial decisions is generally discouraged
How worried are you about your family's ability to communicate well about wealth after you are gone?
1 - Not worried at all
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3
4
5 - Extremely worried
Mentoring & Heir Preparedness
Wealth doesn't prepare heirs — preparation does. This section looks at whether the next generation is being actively developed to receive and steward what's coming, or simply expected to figure it out.
Have you given your heirs pre-inheritance experiences - smaller amounts of money or responsibility to manage, so they can learn and make mistakes while the stakes are low?
Yes - actively manage a shared pool of funds or investments
Starting to introduce these concepts but have not fully implemented them
No - will not manage shared family money until after I am gone
How involved is the younger generation in the family's financial life right now - meetings, decisions, learning?
Yes - age-appropriate involvement and specific roles for them
Occasionally sit in but do not have active roles
No - they are too young to be involved
If you own a business or significant shared assets, is there a documented succession plan for who takes them over and how?
Yes - succession and management plan fully documented and understood by all
Have talked about it but nothing is formally documented
No - have not addressed this yet
How confident are you that the next generation is being actively mentored for the leadership roles they will inherit?
Yes - younger generation is already taking over some of these roles
Still do it all but know I need to pass the baton
No - assume someone will just step up when I cannot do it anymore
Family Purpose & Governance
Families that sustain wealth across generations tend to operate less like a group of relatives and more like an institution — with a shared purpose and agreed-upon rules for how they work together. This section looks at whether that structure exists.
Does your family have a written statement of purpose - a shared articulation of what the family stands for and what the wealth is meant to serve?
Yes - co-created with the younger generations
Yes - but primarily created by me or my spouse
Have strong values but they are not written down as a formal statement
No - do not have a shared purpose statement
Does your family have a governance document - a family constitution, charter, or set of agreed rules for how decisions get made?
Yes - clear living governance document reviewed regularly
Some informal rules but nothing written or formalized
No - make decisions on a case-by-case basis
How does your family approach integrating in-laws into the family's financial culture and conversations?
Actively welcomed with a clear path to participation
Included in social events but excluded from financial or governance meetings
Strict boundaries to keep the wealth only with blood relatives
Does your family hold a regular, structured family meeting to discuss wealth, values, and shared decisions?
Yes - hold an annual family meeting with a structured agenda
Try to but it is inconsistent or lacks structure
No - only gather for holidays and social events
How confident are you that your family has the shared purpose and governance to stay unified across generations?
1 - Not confident at all
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3
4
5 - Extremely confident
Heritage & Storytelling
The course made a striking point: heirs who know where the wealth came from — the struggles, the choices, the story — are far more likely to steward it well. Money without narrative becomes an entitlement; money with narrative becomes a responsibility.
Have you documented your life story and the story of how the family's wealth was built - in writing, video, or recorded conversation?
Yes - fully documented and shared with the family
Started the process but have not finished it
No - but family knows my stories because I tell them often
No - have not documented or shared my story in a structured way
Do your heirs actually know the origins of the family's wealth - the sacrifices, risks, and decisions that created it?
Yes - they understand the history deeply
They know the basics but lack the deeper context
No - they are largely unaware of the history
Have you shared the stories of the people who most influenced you - the mentors, values, and lessons that shaped how you built and view wealth?
Yes - documented this and shared it with my family
Know who it is but have not formally shared the story
No - have not thought about this
Shared Philanthropy
The course framed shared giving as one of the most powerful tools for uniting a family across generations — a low-stakes arena where heirs practice making decisions together, align on values, and experience wealth as a force for purpose rather than just consumption.
Does your family practice philanthropy together - giving as a coordinated group rather than as separate individuals?
Yes - use a Donor Advised Fund or Family Foundation to make shared giving decisions
Give to charity but the decisions are made individually
I make all the charitable decisions for the family
Do not currently have a structured philanthropy plan
Does your family have a shared philosophy for its giving - agreed causes, values, or a mission that guides where support goes?
Give unrestricted funds to organizations we trust
Focus heavily on measuring specific impact and outcomes of gifts
Mix of both
Do not have a specific philosophy
Do younger generations have a real budget or role in the family's giving decisions - actual dollars they help direct?
Yes - actively use this as a training tool
Have discussed it but have not implemented it
No - do not do this
The Collaborative Team & Trust Structures
The structures and advisors you put in place are what carry your intentions forward once you're no longer at the table. This section looks at whether your team and your trusts are built to serve the family's purpose — or just to move money.
Do your professional advisors - attorney, CPA, financial advisor - actually collaborate with one another as a coordinated team?
Yes - meet regularly and coordinate plan holistically
Have all those advisors but they operate in silos
Only have one or two of those advisors
Manage most of this myself
What is your philosophy for selecting advisors who will serve the family across generations?
Specifically sought advisors who prioritize family cohesion alongside tax efficiency
Focused primarily on technical expertise and tax reduction strategies
Have not evaluated my advisors through this lens
Have you clearly defined the purpose of your trusts - what they are meant to accomplish for the family, beyond just holding and distributing assets?
Protect assets while actively enhancing lives and providing opportunities
Protect assets from potential bad decisions creditors or future ex-spouses
Distribute money at specific ages
Do not have trusts set up for my children
Have you written a "letter of wishes" to accompany your trusts - guidance for trustees on your intentions, values, and how you want the wealth to be used?
Yes - provided clear human context for my trustees
No - relying entirely on the legal language in the trust document
Do not know what a Letter of Wishes is
Do the people who will serve as trustees understand the role you expect them to play - not just the legal duties, but the stewardship of family purpose?
Committed to personal development and well-being of beneficiaries
Primarily focused on administration compliance and investment returns
Not sure how my trustees view their role
How much peace of mind do you have about your family's ability to receive, manage, and grow this wealth across generations?
1 - No peace of mind at all
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3
4
5 - Complete peace of mind
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This assessment is designed to provide educational information. It is intended to serve as a framework for discussion with a qualified professional and is not a substitute for professional advice.
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Any projections, estimates, formulas, statistics, or calculations shown are hypothetical in nature and are based on the information you provided, along with standardized assumptions. Actual results will vary. Past performance of investments is not indicative of future results. This assessment is based on national averages and may not reflect your particular situation, therefore it does not recommend any specific insurance product, financial institution or product, plan, or provider.
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The information contained in this assessment does not constitute financial, investment, tax, or legal advice. Scores, calculations, and findings are educational approximations based on the information you provided. Your actual situation may differ materially from any estimates shown. You should consult with a licensed professional before making any decisions.
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Content in this assessment may have been generated in whole or in part by artificial intelligence (AI) systems. While AI can provide valuable educational insights, these systems can make mistakes or produce inaccurate information. The information presented should be used as a starting point for your planning discussions, not as definitive advice. Before taking any actions, consult with qualified professionals who can evaluate your specific situation.
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