For many families, money is such a fraught issue that people would literally rather take the reasoning for their estate planning decisions to their graves than discuss them beforehand.
This lack of candor is sure to cause hurt feelings and even costly litigation when assets are inevitably acrimoniously divided among the remaining family members.
But for advisors who facilitate effective communication between client families ahead of time, the process can instead bond them even closer.
Seth Eisenberg, president and CEO of the relationship education firm the PAIRS Foundation, said estate planning isn’t just about dividing assets — it’s about safeguarding relationships.
“Advisors can play a critical role in preventing future conflict by creating a process that fosters clarity, inclusion and emotional safety for families,” he said. “In my experience, the most intense family disputes don’t erupt because of greed — they come from unmet expectations, unresolved hurt and feeling left out of decisions that deeply impact their sense of identity or belonging.”
Jason Gilbert, founder and managing partner of RGA Investment Advisors in Great Neck, New York, said estate planning, when done well, is about preventing conflict before it begins. He said the best advisors take the time to understand family dynamics, not just the finances.
“In my experience, issues almost never arise from bad math. They come from unmet expectations, surprise decisions or unequal treatment that wasn’t well explained,” he said.
Communication above all
Eisenberg said he has worked with families where the absence of a clear estate plan led to years of estrangement — and others where thoughtful, transparent planning became a healing experience. He said in one case, a family patriarch invited his adult children to a guided conversation “to explore their hopes, fears and feelings” before finalizing his will.
“The result wasn’t just a better legal plan — it was a profound deepening of trust and connection,” he said.
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Gilbert said one of the most effective ways his firm reduces inter-family conflict is by making communication a central part of the planning process.
“We encourage our clients to bring adult children into certain conversations early, not to share every detail, but to build alignment around values, intentions, and legacy goals,” he said. “I’ve seen families fall apart over wills that were ‘technically sound’ but felt like bombshells because no one knew what was coming.”
Gilbert said his firm once worked with a new client whose prior advisor had never addressed estate planning. The patriarch passed unexpectedly, leaving no trust in place, a vague will and significant assets titled improperly.
“It took over a year to unwind, and it created a deep rift between siblings,” he said. “Since then, we’ve helped the family rebuild structure and communication around legacy planning and now, they’ve come full circle with regular family meetings that we help facilitate.”
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Eisenberg said advisors can help reduce conflict by encouraging families to start conversations early and revisit them regularly, use neutral facilitators or structured tools to explore emotional reactions, put communication in writing — including the “why” behind decisions, clarify roles and responsibilities within trusts and wills, and encourage legacy letters that share values and intentions, not just directives.
“Ultimately, the goal isn’t just avoiding court — it’s protecting what matters most: the emotional well-being of the people we love,” he said.
Mackenzie Richards, partner and relationship manager at SK Wealth Management in Providence, Rhode Island, said while estate planning documents are critical, “ideally we like to see clients have these important, but sometimes tough or awkward conversations while they’re still above ground.”
“There are so many ways questions that can pop up that will lead to frustration, anger and, very possibly, family infighting,” he said. “‘Why is my inheritance left in a trust? Why did my brother or sister get more? Why did they get the beach house and I got the investments? Why is my brother or sister the executor and not me?’ Almost all of the time these questions can easily be explained away with communication ahead of time. Most of the time these decisions are not rooted in actively trying to treat children differently, but are more procedural and administrative decisions than anything.”
Keep it equal, or at least explain why not
Evan H. Farr, principal attorney at Farr Law Firm in Fairfax, Virginia, specializes in estate planning and elder law and said being fair is key to avoiding family fights.
“Obviously that begs the question, ‘What is fair?'” he said. “For most people, fair means leaving their assets to their children in equal shares. I would estimate that about 90% of parents leave their assets to their children in equal shares, ‘per stirpes,’ [which] means that if a child dies before the parent leaves behind children, the share of the deceased child goes to the children of the deceased child. Almost all parents do this because of perceived ‘fairness.’ Most parents are worried that if they leave unequal amounts, their kids will fight, and this is predictably accurate.”
Farr said unequal distributions often do lead to family fights and prolonged and expensive litigation, but “fair” does not always mean equal.
“Some parents will leave more money to children who need it more, often if that child chose a noble but low-paying profession, such as a teacher or front-line worker.,” he said. “And, of course, a parent with a child with special needs will often leave more money, in a special needs trust, for the benefit of the child with special needs.”
John W. Loyd, owner of The Wealth Planner in Fort Worth, Texas, said the “big thing” is to equalize or prepare clients to share the reasons why not.
“If you don’t, best to explain to family members while alive the rationale,” he said. “For example, some clients want to reward bad behavior; giving more to the consistently unemployed child versus the hard-working, successful child who owns their own business. I try and get clients to think about these things logically versus emotionally.”
