Lisa McCurdy

Karen Alston

I've spent three decades counseling ultra-high net worth families, focused on multiple generations of families and multiple arms of the family tree. Over the years of managing an estate planning law practice, I've come to understand that families seldom have a deliberate, purposeful conversation about what sustains them as a family, and this often proves to be a barrier to planning. Ninety-one per cent of all wealth transfers fail before getting past the third generation, validating the "shirtsleeves to shirtsleeves in three generations" expression we have all heard many times. Those that are rebuilding in Gen 3, have failed to address the family dynamic and align around common mission – placing successful tax-advantaged generational wealth transfer and wealth preservation out of reach.

Families often assume that technical perfection equals security. Human behavior is the weakest link. A $100 million trust can be undone by mistrust, jealousy, or lack of shared vision. Courts see endless cases where heirs fight over minutiae, destroying both wealth and relationships, largely because of hurt feelings related to issues not addressed prior to a family leader's death.

While 86 per cent of families view "life lessons and values" as essential to inheritance, many still struggle to communicate these effectively across generations. 

So how do we move UHNW families to meaningful dialogue?

In a nutshell, communication matters.

Successful families can navigate difficult conversations, gain consensus, and align around common vision – all while honoring multigenerational differences. Each generation has their distinct communication styles, preferences, and expectations, which introduce a unique set of obstacles.

During my fireside chat, I integrated cutting-edge technology with timeless human wisdom, which helps families shift from anxiety-driven planning to purpose-driven dialogue. Specifically, I shared how families can use AI as a catalyst for meaningful, values-driven conversations, helping them articulate shared principles, prepare the next generation for responsible wealth stewardship, and move to stronger, more successful multigenerational families.  

Key takeaways:
-- AI helps solve the family communication challenge, not by replacing human connection, but by deepening it; 
-- AI can be a catalyst for meaningful conversations that bridge generational divides, articulate shared values, and prepare the next generation for responsible wealth stewardship, recognizing the unique generational differences in communication style; and 
-- For those just getting started, I recommend top-rated known platforms, such as ChatGPT, Microsoft Copilot, Google Gemini.

Where should AI end and human experience begin?
AI excels at patterns and scale: It can process vast amounts of data, recognize trends, and simulate conversation with remarkable fluency. Human expertise is irreplaceable in judgment and lived experience: Empathy, moral reasoning, and the ability to connect through shared vulnerability are uniquely human. AI can mimic emotional tone, but it doesn't feel; it doesn't carry the weight of lived experience, cultural nuance, or personal history. The boundary is authenticity.

What privacy controls should be recognized?
Given the highly sensitive nature of family dynamics and financial information, data minimization and purpose limitation are essential. Collect only the data strictly necessary for the task, avoid storing sensitive details unless essential, and ensure that data is used only for the purpose intended. 

You must treat family and financial data as the most sensitive category, applying maximum safeguards from collection to deletion. My guiding principle: If you wouldn't post it publicly or email it unencrypted, don't share it with an AI assistant.

AI is not a replacement for human empathy but a scaffolding tool, helping families prepare, moderate, and navigate emotionally-charged discussions. By combining structured facilitation with AI-driven insights, UHNW families can move from transactional debates to purpose-driven dialogue that preserves both wealth and legacy.

Disclaimer: Nothing in this content is to be construed as creating an attorney-client relationship. Additionally, none of these resources are to be considered legal advice. Content and resources provided are meant for educational and informational purposes only. The author is not liable for any losses or damages related to actions or failure to act related to the content, downloads, or resources made available through this content.