📋 Key Takeaways
- Choosing a trustee based on love alone is one of the most common — and costly — mistakes families make. A good trustee must be organized, financially savvy, compassionate, fair, firm, and available.
- Family member trustees can work beautifully in functional families, but can devastate relationships when dynamics are already strained. Professional (corporate) trustees are often the smarter choice when conflict is likely.
- Florida’s diverse communities — including many families in Orlando, Winter Park, Windermere, and across Orange, Seminole, Lake, and Osceola Counties — face a specific pitfall: naming a non-citizen trustee, which can trigger serious tax consequences.
- Clear “rules of the road” written into the trust document give trustees documented authority to say no — and protect them from being blamed personally for doing so.
- Successor trustees, professional support teams, and honest conversations about beneficiary weaknesses are all essential parts of getting trustee selection right.
Introduction
When most people sit down to create an estate plan, they spend a lot of time thinking about who gets their assets — and not nearly enough time thinking about who manages those assets along the way. That’s where the trustee comes in, and it’s one of the most consequential decisions in any estate plan.
In this episode of Life, Legacy and Wealth, Tom Moss — an estate planning, special needs planning, probate, and elder law attorney at Sawyer & Sawyer, P.A. — breaks down everything families need to know about choosing the right trustee. Tom serves families throughout Orlando, Windermere, Winter Garden, Winter Park, Dr. Phillips, Horizon West, and across Orange, Lake, Osceola, and Seminole Counties, and he brings decades of experience to one of the most personal and often overlooked decisions in estate planning.
What Does “Choosing the Right Trustee” Actually Mean?
Most families assume that choosing a trustee means picking someone they trust — and naturally, that means someone they love. Tom Moss says that instinct, while understandable, is one of the biggest mistakes he sees.
Tom Moss: “The biggest mistake families make is just picking someone they love. Love is great for relationships, but love doesn’t always equate to a great trustee. When I say you need to pick a good fiduciary, that’s someone who’s going to be organized, responsible, fair — but also firm. A lot of times the person you love most isn’t that person.”
A fiduciary, in simple terms, is a person placed in the highest legal position of trust, with an absolute duty to act solely in the beneficiary’s best interest. They avoid personal conflicts and are held to the highest standard of diligence. And as Tom points out, the trustee controls everything you’ve worked your whole life to build. Depending on your beneficiaries’ circumstances — disability, addiction, financial immaturity — this responsibility can last for generations.
What Does a Trustee Actually Do?
The first job of any new trustee is to inventory the assets — understand exactly what they’re controlling, review the accounts and investments, ensure real property is properly insured, and determine who the beneficiaries are and what the assets are meant to accomplish. From there, they administer the trust according to its terms and their fiduciary duties.
It’s worth understanding how a trustee differs from an executor or personal representative. If a trust simply says “pay my debts and distribute to my kids,” the roles look similar. The real distinction is oversight.
Tom Moss: “A personal representative is court-appointed — there’s an attorney involved, a judge watching. With a trust, there’s no required court oversight and no mandatory attorney involvement. That can be both a benefit and a risk. And in a continuing trust — one that goes on for years — the trustee’s responsibilities are substantially greater than anything an executor faces.”
Florida law also requires trustees to provide annual accountings to beneficiaries, a detail Tom says is frequently overlooked by families who assume the role is informal.
The Qualities That Make a Trustee Effective
Being good with money is essential — but it’s never sufficient on its own. Tom identifies several qualities that families frequently overlook when selecting a trustee:
- Compassion. “I may have a son who went to Harvard and he’s a number guru — but he’s not a compassionate person. The people in a continuing trust usually have real challenges in their lives. Someone has to actually care about them.”
- Willingness to listen. “I don’t expect my trustee to be a professional on day one. I want them to listen to the CPAs, the attorneys, and not be a know-it-all. That’s one of the most damaging traits in a trustee.”
- Organizational skills. Inventorying and managing assets over time requires real diligence. Florida-required annual accountings don’t happen on their own.
- Fair but firm. “It’s like being a good parent. It’s harder to say no than yes, but sometimes the right answer is no. A trustee has to hold that line.”
- Availability. “I can have a brother who is the best business mind in the world, but if he works 23 hours a day and doesn’t return texts, he’s not going to be a good trustee — no matter how capable he is.”
Family Dynamics: Where Conflict Is Born
One of the most candid parts of Tom’s discussion is about what actually happens to family relationships when a sibling or family member steps into the trustee role.
Tom Moss: “All of a sudden you’re not just someone’s brother anymore — you’re the gatekeeper. That relationship shift brings out a lot of what people think are injustices. ‘He never liked me. I can’t believe my parents did this.’ It becomes very personal.”
Trusts are often created specifically because a beneficiary has challenges — overspending, addiction, disability, or poor financial judgment. That means the trustee’s job frequently involves saying no. And when you’re telling your sibling no, it stops feeling like trust administration and starts feeling like a family fight.
Tom also flags two trust-drafting problems that can unintentionally create conflict down the road:
- Too much discretion. A broad standard like “health, education, maintenance, and support” sounds reasonable — but it leaves enormous room for disagreement. One person thinks a new car every year qualifies. The trustee disagrees. Now it’s personal.
- Too many restrictions. Trying to predict every future scenario in a document that may last 50 years is unrealistic. Overly rigid requirements can become impossible to fairly enforce, and mandatory conditions that can’t account for life’s changes often backfire.
Tom Moss: “Guidance is okay. I think that’s important. But when you make things mandatory and try to predict everything that’s going to happen in the future, you have to be very careful — because none of us can see that far ahead.”
Family Member vs. Professional Trustee: How to Decide
For functional families, Tom firmly believes that no professional can replicate what a loving family member brings to the trustee role. But he’s equally clear that not every family is functional — and choosing a family member trustee in the wrong situation can do lasting damage.
Tom Moss: “If I care about my brother and I love my brother, I’m going to try to do what’s best for him. There’s simply no replacement for that. However, some families aren’t entirely functional, and that can create conflict. Professional trustees do this every day — they have investment decisions, tax decisions, and compliance infrastructure. The downside is that the Bank of America doesn’t love your brother the way you do. That’s not a fault of the professional. It’s just the reality.”
The clearest signal to go the professional route? When the beneficiary is combative, when the family has a documented history of conflict, or when the trustee role would genuinely damage or destroy a sibling relationship.
Tom Moss: “If your two kids have never gotten along their whole life and can’t sit at the same Christmas table, don’t set it up for failure. You’re just putting two people who are going to hate each other even more.”
What About Co-Trustees?
Naming two family members as co-trustees can work well — shared workload, built-in backup coverage — but only when the relationship is solid. When it isn’t, Tom warns it can make things worse: conflicting decisions, one trustee undermining the other at the bank, complete gridlock.
Tom Moss: “The history of your children is going to tell you a lot. Did they fight every day since they were 12? Then you’re going to appoint them to work together now?”
Red Flags and Common Mistakes in Trustee Selection
Non-Citizen Trustees — A Central Florida Caution
This is a mistake Tom sees often, especially in the diverse communities across Central Florida.
Tom Moss: “We have a lot of different nationalities here, and a lot of times people want to choose a brother who’s still in Brazil. That could be a red flag immediately. Choosing a non-citizen trustee can result in negative tax consequences. Make sure you’re naming a qualified trustee.”
Other Common Pitfalls
- Naming someone without asking them. Never assume willingness. A financial advisor being good with money doesn’t mean they want to be the legal guardian of your family’s assets — or the authority figure over your children.
- Naming elderly trustees without a succession plan. A trust can last decades. Naming an 85-year-old without identifying successors creates an immediate problem.
- Keeping the peace at the expense of good judgment. Naming co-equal trustees just to avoid hurt feelings often creates more conflict, not less. Tom’s advice: cater to each person’s strengths. One child may be financially sharp; another may be deeply compassionate. One becomes trustee; the other, healthcare surrogate. Let their strengths guide their roles.
Writing Clear Trust Instructions to Reduce Conflict
One of Tom’s most practical recommendations is building a “rules of the road” section directly into the trust document — written guidance that gives the trustee documented backing when making difficult decisions.
Tom Moss: “In a lot of trusts, I have a section with desired behaviors — what the parents want the beneficiary to be doing before distributions are made. Things like: be employed, don’t be breaking the law, take care of your health. That way the trustee can say, ‘I’m not withholding this money because I don’t like you. It’s because your parents set these expectations, and you’re not meeting them.’ That’s a very different conversation.”
Every trust should be customized to the family. Tom encourages clients to go beyond the template and add their own values and expectations. The document should reflect who they are — not just a standard form.
On the question of whether to hold a family meeting while the grantor is still alive: Tom says it depends entirely on the family. For cooperative, functional families, it can eliminate surprises and reduce future disputes. For families with deep conflict, forcing that conversation can put an unnecessary and painful burden on an aging parent.
Florida-Specific Considerations for Trustee Selection
Beyond the citizenship issue, several Florida-specific circumstances affect trustee selection:
- Real estate and rental properties. A trustee managing Florida rental properties needs to understand landlord responsibilities, property management, and insurance. An out-of-state trustee who refuses to hire a management company and isn’t physically checking on properties is creating serious risk.
- Business owners. If the trust includes an active business, trustee selection becomes even more critical. Most family businesses fail within one generation — not because the next generation is incapable, but because there’s no real succession plan. The trustee must be able to work with key employees and ensure continuity.
- Blended families and second marriages. These situations add complexity to both the structure of the trust and the dynamics around trustee selection, requiring careful, individualized planning.
Building a Professional Support Team
Individual trustees don’t have to go it alone — and Tom emphasizes that the best outcomes happen when a trustee is supported by a vetted team of professionals.
Tom Moss: “Go meet with the financial advisor you trust now. Go meet with a good CPA now. Go meet with a good attorney now — so that when you’re gone, your trustee isn’t starting from scratch or getting sold a bad product by someone they don’t know. Having that team already in place is one of the most valuable things you can do.”
Next Steps: How to Get Started
If this conversation has made you realize your current trustee choice might need a second look, Tom’s recommended first step is straightforward: sit down — alone or with your spouse — and honestly assess whether you want an individual trustee or a corporate trustee. If individual, make a list of candidates and evaluate their real strengths and weaknesses. If corporate, identify which local banks have trust departments and set up meetings.
Then bring that thinking to your estate planning attorney. The questions a good attorney will ask: What are this beneficiary’s strengths and weaknesses? Are there issues with addiction, spending, an abusive relationship, or financial instability? Would you trust this person with your money right now?
Tom Moss: “Make sure the people you choose are not only capable — but available. And make sure they understand what they’re agreeing to. It’s not a small job. It is a continuing responsibility, for as long as that trust is in place.”
Ready to Choose the Right Trustee for Your Family?
Trustee selection is one of the most important — and most personal — decisions in your estate plan. Getting it wrong can cost your family far more than money. Tom Moss and the team at Sawyer & Sawyer, P.A. help families throughout Orlando, Winter Park, Windermere, Winter Garden, Dr. Phillips, Horizon West, and across Orange, Lake, Osceola, and Seminole Counties think through these decisions with clarity, compassion, and decades of real-world experience in estate planning, special needs planning, probate, and elder law.
Call us at 407-909-1900 or schedule a consultation online to start the conversation. Your family’s legacy deserves a plan — and the right people to carry it forward.
