One of the challenges for advisors serving ultra‑high net worth clients is managing the complex tasks of wealth transfer. Firstly, there are a number of groups involved, each with their own interests and goals that can conflict with others: heirs, businesses, foundations and trusts.
To complicate matters, heirs can belong to different generations and have different styles of communication and emotional sensitivities. A 2026 J.P. Morgan survey found that a majority of millennials and Gen Z respondents cited emotional factors as a significant challenge in family discussions about wealth, compared to 38% of Gen X and 29% of baby boomers.
Inheriting wealth is a complex, emotional process — one that reveals underlying family dynamics and life choices. People often don’t like to talk about money, which heightens the risk of conflict because of misunderstandings and unclear agendas.
“Start by naming the tension out loud. Families often avoid it, and silence tends to let it grow,” said Justin Bakewell, Head of Client Strategy, Pitcairn.
Advisors, therefore, should know what to do — and what not to do. Their role should be to facilitate and illuminate, experts say, enabling productive conversations and making the process of wealth transfer as clear and transparent as possible to everyone involved.
Advisors should help families make their own decisions rather than act as referees. If necessary, advisors should turn to outside groups with more expertise in areas like mediation and conflict resolution, such as attorneys and psychologists.
“Self‑awareness and humility are crucial as advisors, especially when it comes to our limits and when to bring in other experts,” said Jason Oclaray, President of Angeles Family Office. “That will be different for each advisor, client, and situation, which makes bringing in outside advice more of an art than a science.”
Managing Various Interests
Advisors often encounter people and institutions with diverging goals for giving and receiving wealth. Keeping everyone informed and talking to each other are key challenges.
“The reality of wealth means that all families have competing interests at times, each tied up with emotional and psychological implications,” Oclaray said. “The most valuable advisors act as fiduciaries, laying out options, identifying trade‑offs, and facilitating sometimes‑challenging discussions to arrive at the best outcome possible. Wealth means complexity, and our responsibility is to simplify as best we can.”
With so many parties involved, advisors should identify which clients they represent and the obligations owed to each, said Benjamin Renzo, Head of Family Office, Simon Quick Advisors.
“The starting point is identifying who the client is,” Renzo said. “Advisors owe a fiduciary duty, and whether that duty is to an individual client, their adult children, a trust, entity, or several parties, shapes our obligations, including how advice and work product could be used in litigation, and whether you can or should continue advising all parties once interests become adverse.”
Different Generations, Different Views
Baby boomers’, Gen X’s and millennials’ unique ways of seeing wealth could lead to disagreements about the purpose of money and how and when heirs should receive it.
“The biggest gap is usually purpose, not investment preference,” Bakewell said. “Founders often see wealth as something to protect. Rising generations may see it as a tool for impact, independence or a different kind of life. When those views go undiscussed, resentment can erode trust faster than any market downturn.”
Said Renzo: “Unresolved family issues and mixed messages about the purpose of wealth are common threats, along with misaligned values across generations, and too little time spent understanding how the next generation reasons and their perspective on wealth. Breakdown and lack of conflict‑resolution skills compound this, as does underestimating the impact and risk of small decisions.”
“Between generations, the greatest threats are time and taxes,” Oclaray said. “Younger adult generations often want assets and authority shifted to them as they mature, perhaps sooner than the first generation is ready. And sometimes, younger generations don’t consider the effect of ‘subtract (for taxes) and divide (for siblings)’ on generational wealth.”
Preparing Heirs For Wealth
Large amounts of money can fundamentally change lives. That’s why advisors should help prepare clients for how to responsibly manage new wealth, including honest conversations about values, mission and past mistakes.
“It starts at home,” Renzo said. “Families that truly engage, taking time to walk heirs through how wealth is managed, from values and principles to the actual decision‑making process, tend to fare better. Sharing past mistakes and hard lessons matters too. That candor builds perspective, connection, and trust well before any inheritance changes hands.”
Said Oclaray: “Heirs should be prepared as early as possible through communication, planning, and participation. Meaningful responsibility is something learned over time. A large liquidity event, whether an inheritance, sale, or lottery win, can be very difficult and disorienting without a pre‑existing framework of meaning.”
Such talks should happen sooner than later.
“Preparation should start years before the transfer, and it should be gradual,” Bakewell said. “Heirs benefit from age‑appropriate financial education, real responsibility with real money and a clear understanding of the family’s values. We encourage parents to share the ‘why’ behind their plans, not just the numbers. Heirs who feel trusted and capable are more likely to build purposeful lives.”
Family Versus Businesses, Trusts, Foundations
Wealth transfer is already a fraught process, because of the emotional dynamics and relationships among family members. In other words, inheriting money can be intensely personal.
But what about professionally managed institutions, such as businesses, trusts and foundations, that also receive wealth? Those groups present a plethora of goals, governance and legal situations that can greatly complicate the situation.
“They blend family roles with formal ones,” Bakewell said. “A sibling may also be a trustee, a board member or an employee, and each role carries different obligations. Decisions that make sense for the entity can feel personal at the dinner table. Without clear governance, overlapping roles can strain even close relationships.”
Said Renzo: “Businesses often have other owners and principals whose objectives and views differ from the family’s. Trusts are administered by trustees who typically hold broad discretion over distributions, which does not always align with beneficiaries’ expectations. Foundations without a clear succession plan and decision‑making process can further complicate family dynamics.”
“Clients with complex business, estate, and philanthropic goals face real‑world trade‑offs,” Oclaray said. “One second‑generation client jokes that his family’s favorite charity amounts to an ‘extra sibling.’ Skillful advisors should clarify those trade‑offs so the client can make meaningful decisions. Communication plays a key role to manage expectations throughout the family.”
Facilitate, Not Referee
Advisors need to clearly understand the best role they can play in managing disagreements and conflicts among family members. They can help families develop strategies and structures for resolving disputes while leaving decisions to the family.
“Advisors should act as facilitators, not referees,” Bakewell said. “We help families build the structures that make hard conversations possible, including family meetings, decision‑making frameworks and clear communication norms. When disagreements arise, our role is to bring objectivity, surface each perspective and keep the conversation anchored to shared goals. The family should own its decisions. We help them get there.”
“Advisors should act as facilitators, not referees.” — Justin Bakewell, Head of Client Strategy, Pitcairn
Said Renzo: “Advisors should function almost like a general manager of family governance and during any disagreements. Understanding the full picture, family dynamics, history, risks, personalities, values, and objectives is essential to identifying the right third parties and strategy. It is equally important to recognize that not every family member will want you as their advisor, now or in the future.”
Oclaray emphasized anticipating and avoiding conflicts.
“The value of a true family office is in knowing clients and family dynamics intimately and in being able to help them anticipate and avoid conflicts even before they arise,” Oclaray said. “That’s the challenge of our work—sometimes the most valuable work we do is in avoiding a problem in the first place.”
Recruiting Outside Help
Advisors need to know when to call for additional expertise.
“As early as possible, and before a conflict hardens,” Bakewell said. “Attorneys and trustees belong at the table from the start of any complex plan. When emotions begin driving decisions, a family psychologist or mediator can help more than another spreadsheet. Knowing the limits of our role is part of serving families well. A coordinated team tends to produce the best outcomes.”
Oclaray agrees.
“A rule of thumb is: Early and often, without being wasteful,” Oclaray said.
“Bring in attorneys when litigation is threatened or claims arise, or when there are concerns about disclosing certain information,” Renzo said. “Involve psychologists when perspectives on wealth or decision‑making diverge sharply, or when personal history, physical health, or mental distress have strained family relationships. Turn to mediators once other dispute resolution efforts have failed, understanding upfront whether that mediation will be binding.”
Thomas Lee, Senior Editor and Staff Writer for Wealth Solutions Report, can be reached at thomas.lee@wealthsolutionsreport.com.
