Coordinated Counsel
How to Avoid Problems with Dissatisfied Beneficiaries
Transcript
BARRY: I would say that number 10 on our list, which was where we intended to start–
CHAD: I was going to ask about that. You know, we spent this whole time really talking about all the documents that you can put together and the planning you can do to avoid negative outcomes. But even with these documents in place, what are ways that someone who maybe feels like they’re getting screwed over–? What are some things that they can do to challenge some of these predetermined outcomes?
BARRY: I call them unhappy beneficiaries. Not because they’re not happy in general, but they’re dissatisfied with their inheritance. I assume there’s an estate planning document. So there’s like a will or a trust. Say, for example, there’s no trust. There’s just a will. There’s really only a couple of ways they can do that.
I would say they can attack it from an angle of lack of capacity. They didn’t know what they were doing. They didn’t understand the nature of their assets or who was going to get what. They just didn’t know. In that context, that is a legal determination, not a medical one. Doctors don’t like hearing that. It’s actually not a medical determination. You have the legal capacity. And when you have dementia or Alzheimer’s, you have clear days and bad days. Cloudy days and clear days. Alternating. Some worse than others. All that matters is that you were clear on the day and at the time that you signed those documents.
You’re thinking, “Oh, that’s so easy to do.” But not when someone is making a challenge and bringing medical records showing you were on medication and that a week ago you didn’t know what your name was. Those are bad facts. That becomes an invitation for somebody to argue lack of capacity. You should definitely be planning before that happens.
The second way– Remember when we talked about the good child, bad child, and medium child? Someone might claim that another person was controlling you or telling you to do this, and you did it out of fear or misplaced trust. You were compelled to do it. You were under duress. Challenging under that argument is like–
CHAD: Undue influence, right?
BARRY: The ketchup and a hot dog. You usually see both of them. You do not typically see just one. They come together most of the time.
The third way to challenge documents — and believe it or not, this happens all the time — is to argue that the documents were not validly executed. They were not validly executed. There are strict rules on how to do it. Many online solutions do not do that part for you. They include disclaimers where you sign away liability. As a result, you can have someone who believes they have a good document for 50 years, and then they pass away never really knowing just how vulnerable they really were. A deposition can easily uncover flaws in how the document was executed.
You asked me earlier how we handled document signings during COVID and how we complied with the law. And we are doing it. We’re doing it creatively. Also, in Florida, something else changed recently. On July 1st– It’s October already!
CHAD: I know, it’s crazy.
BARRY: It’s been a long March. On July 1st, electronic execution of wills and trusts became acceptable. It’s not like a DocuSign. It’s not like you can just take a Zoom call and sign a document and you saw me do it. It is actually quite complicated. We offer that service for certain documents, except for wills. The reason is that electronic wills require something called a qualified custodian who must store the document for something like 100 years. It’s just not practical. It’s easier to get in the car, meet in person, and sign the documents the traditional way. E-signing is becoming a reality, and I am sure it will be litigated because there are still holes in the system.
But going back to challenges, the main arguments are lack of capacity, undue influence, or flaws in execution. And of course e-signing. You’re setting yourself up if you wait too long, or if there are bad facts and you have a dissatisfied beneficiary. There will be an attorney willing to take that case. If there is money in there, they will take the case. They will make the argument, and many of those cases end up settling.
That is why we focus so much on strengthening documents and planning properly. It helps prevent those challenges before they ever begin. And that’s something we uncover pretty quickly.
One of the Most Overlooked Parts of Estate Planning? Communication
By: Barry E. Haimo, Esq.
March 19, 2026
Estate planning is often viewed as a legal process focused on documents. Wills, trusts, and beneficiary designations are essential tools that determine how assets transfer after death. However, one of the most common sources of conflict in estate administration has little to do with the documents themselves. It has to do with communication — specifically, the lack of it.
Families are often surprised by how quickly misunderstandings can escalate into disputes when expectations are unclear. In fact, many estate conflicts begin not because the legal plan is flawed, but because beneficiaries are caught off guard by the outcome.
The Problem with Unspoken Expectations
In many families, estate planning decisions are made privately. Parents may create or update a will without discussing it with their children. They may assume their intentions are obvious or believe that discussing inheritance will create unnecessary tension.
Unfortunately, silence can create even bigger problems.
When family members do not understand the reasoning behind certain decisions, they may interpret the outcome in ways that were never intended. A child who receives a smaller inheritance may assume favoritism or manipulation, even when the decision had practical reasons behind it.
For example, one child may have already received financial help during the parents’ lifetime, such as assistance with a home purchase or education. Another child may inherit a family business because they have been working in it for years. Without context, these decisions can appear unfair.
Transparency Can Reduce Conflict
While every family dynamic is different, many estate planning professionals encourage some level of transparency about major decisions. This does not mean that every financial detail must be shared. Instead, it can involve discussing general intentions and explaining the reasoning behind certain choices.
When beneficiaries understand the broader goals of an estate plan — such as protecting a family business, supporting a surviving spouse, or ensuring financial stability for future generations — they are often more likely to respect those decisions. Even a brief conversation can reduce confusion and prevent assumptions that might otherwise lead to disputes.
Choosing the Right Decision Makers
Another area where communication matters is the selection of fiduciaries. Executors, trustees, and agents under powers of attorney all carry significant responsibility. These roles require time, attention, and sometimes difficult decisions. When someone is named to serve in one of these positions, it is helpful for them to know in advance what the role involves.
Discussing these responsibilities beforehand can prevent surprises later and ensure the person is willing and prepared to serve.
Updating the Plan as Life Changes
Family dynamics evolve over time. Marriages, divorces, new children, blended families, and changes in financial circumstances can all affect an estate plan.
Regularly reviewing and updating planning documents allows families to address these changes thoughtfully rather than leaving outdated instructions in place. It also creates opportunities to revisit conversations with family members and clarify intentions as circumstances evolve.
Planning for More Than Assets
Estate planning is ultimately about more than transferring property. It is about providing clarity, minimizing conflict, and helping families navigate a difficult time with fewer uncertainties.
Clear communication cannot eliminate every disagreement, but it can go a long way toward ensuring that the plan reflects not only legal strategy, but also the values and relationships it is meant to protect.
Want a calm, professional voice there with you for these conversations? Get in touch. We can help you both create the plan you want and communicate that plan to those you care about.
And if you’re interested in getting all of your advisors on the same page, get in touch with Kinnect Financial.
