By Ilya Lyubimskiy, JD, CPA | Estate Planning & Probate Attorney and Author of I Wish I Talked to You Sooner
One of the most important estate planning decisions has nothing to do with who inherits your property.
It is deciding who you trust to carry out the plan.
People often approach this decision almost automatically.
“My spouse first.”
“Then my oldest child.”
“My sister lives closest.”
“I have three children, so I should name all three.”
Sometimes those are excellent choices.
But estate planning roles are not awards for the person you love most. They are jobs that require different skillsets.
A beautifully drafted estate plan can become much harder to carry out if the wrong person is placed in charge.
First, Understand the Different Jobs
Estate plans can include several people with very different responsibilities.
A personal representative (a/k/a executor) is the person responsible for administering the probate estate after death. Colorado courts use the term “personal representative” for the person appointed to administer the estate.
A trustee manages property held in a trust according to the trust’s instructions.
A financial agent acts under a financial power of attorney and can handle authorized financial matters while you are alive.
A healthcare agent makes healthcare decisions when you cannot make or communicate those decisions yourself.
Sometimes the same person can serve successfully in several roles.
Sometimes that would be a terrible idea.
The question is not simply:
“Who do I trust?”
It is:
“Who do I trust to do this particular job well?”
The book makes this point directly: personal representatives, trustees, and agents have real legal responsibilities, and choosing the people who will carry out the plan can be just as important as drafting the documents themselves.
Being the Oldest Child Is Not a Qualification
Naming children in birth order is incredibly common.
Oldest child first. Then the second. Then the third.
It feels orderly and fair.
But age does not necessarily tell you who is best suited to manage an estate, trust, or financial affairs.
Maybe your oldest child is wonderful but hates paperwork.
Maybe another child works in finance, keeps impeccable records, and is comfortable dealing with accountants and attorneys.
Perhaps one child is constantly overwhelmed with their own responsibilities while another has more time and flexibility.
Those facts matter more than birth order.
The same applies to a spouse, sibling, or close friend. The closest relationship does not automatically produce the strongest decision-maker.
The book specifically warns against treating these appointments as a matter of family hierarchy rather than skill, temperament, and responsibility.
What Makes a Good Personal Representative?
Administering an estate can involve much more than reading a will and handing out property.
The person in charge may need to locate assets, communicate with beneficiaries, work with attorneys and accountants, address creditor issues, keep records, manage property, and eventually make distributions.
So consider someone who is:
- responsible and organized;
- comfortable with paperwork and deadlines;
- able to communicate with different family members;
- willing to ask professionals for help when necessary; and
- capable of staying reasonably neutral when emotions run high.
They do not need to be an attorney or accountant.
But they should be someone who can manage a process without ignoring it for six months because paperwork makes them miserable.
Reliability is often more valuable than financial sophistication.
What Makes a Good Trustee?
A trustee may have a much longer job.
Depending on the trust, the trustee could be managing assets for years.
Imagine a trust created for young children.
Or a trust designed to provide for a surviving spouse during life and then distribute remaining assets to children.
Now the trustee may have to manage investments, keep records, make distributions, communicate with beneficiaries, and exercise judgment over an extended period.
That requires a different level of commitment.
Ask:
- Can this person manage money responsibly?
- Can they follow instructions rather than substitute their own preferences?
- Will they keep good records?
- Can they say “no” when necessary?
- Can they deal fairly with beneficiaries who may want different things?
And perhaps most importantly: Can this person handle the relationships surrounding the trust?
Someone can be excellent with money and terrible at managing family conflict.
In some trusts, both skills matter.
The Best Financial Agent May Not Be the Best Healthcare Agent
We touched on this in the financial and medical power-of-attorney articles, but it is worth repeating.
Different people can be good at different things.
You might have one child who is extremely organized, financially sophisticated, and comfortable dealing with banks.
Another child may live nearby, remain calm in medical emergencies, and be better at communicating with physicians.
There is nothing unfair about recognizing those differences.
In fact, the book gives exactly this kind of example: one family member may be better suited for financial responsibilities while another is more available and better equipped for healthcare decisions. The problem arises when no one understands the reasoning behind those choices.
Estate planning should match responsibilities with abilities.
It is not necessary to give everyone the same job simply to avoid hurt feelings.
Geography Still Matters
Technology makes distance much less important than it used to be.
People can sign documents electronically, attend meetings remotely, access accounts online, and communicate from almost anywhere.
Still, geography can matter.
A healthcare agent living nearby may be more readily available during an extended hospitalization.
A trustee managing real estate may benefit from understanding the property and local circumstances.
A personal representative who lives across the country can absolutely serve in many situations, but travel and logistics may make the job harder.
Distance should not automatically eliminate your best candidate.
It should simply be part of the analysis.
Always Have a Backup
Your first choice may be perfect today.
That does not mean they will be available ten years from now.
People move. Health changes. Relationships change. Sometimes a person who originally agreed to serve later decides the responsibility is more than they can handle.
That is why successor decision-makers matter.
Ask yourself:
“If my first choice cannot serve, who is next?”
And sometimes:
“Who is the backup to the backup?”
A plan that depends completely on one person can develop a significant hole when that person is no longer available.
The book emphasizes that the right appointments and the right backups help create a plan that can continue functioning when circumstances change.
Talk to People Before You Name Them
This sounds obvious.
It is surprisingly easy to skip.
Do not make someone discover after an emergency or death that you appointed them to a major fiduciary role years earlier.
Ask first. Then explain what the role involves. Ask whether they are comfortable serving. They may tell you something important. Perhaps they are overwhelmed caring for a child with special needs. Maybe they expect to move overseas. Perhaps they have a demanding career and know they would struggle to administer a complicated trust.
Or maybe they simply do not want the responsibility.
That is useful information to have before the document needs to work.
The book makes this wonderfully practical point: estate planning works better when these appointments are not surprises.
When Might a Professional Fiduciary Make Sense?
Family and friends are not the only options.
In some circumstances, a professional fiduciary or trust company may be worth considering.
That may be especially useful when:
- beneficiaries have significant conflict;
- the assets are complicated;
- no family member is well suited for the responsibility;
- neutrality is particularly important; or
- the role may continue for many years.
Professional help comes with cost, of course.
But the tradeoff can be experience, continuity, recordkeeping, and neutrality.
The book also notes that some families use a hybrid approach. Naming a family member first and a professional as successor just in case circumstances later change.
This does not mean professionals are always better than family.
It simply means you have options.
Don’t Choose Based on Who Might Be Offended
This may be the hardest part.
Parents understandably worry about how children will interpret these decisions.
“If I name my younger daughter instead of my oldest son, will he think I trust her more?”
Maybe.
Which is why communication matters.
You can explain:
“I chose her because she is very organized and works with financial matters every day.” Or: “I chose him as healthcare agent because he lives nearby and can respond quickly.”
Choosing different people for different roles does not mean you love one person more.
It means you took the responsibilities seriously. The people named in your estate plan are there to perform a function, not receive a family honor.
The People Are Part of the Plan
People understandably focus on documents. But even perfectly drafted documents eventually depend on human beings.
Someone has to answer the phone.
Someone has to gather the records.
Someone has to speak with the bank.
Someone has to make the difficult decisions.
Someone has to explain things to the family.
That is why one of the strongest ideas in I Wish I Talked to You Sooner is that these roles are jobs, not honorary titles.
Choose people because they can do the job.
Give them backups.
Tell them what you expect.
And make sure they know where to turn for help.
Because the right person can make a difficult process much easier.
The wrong person can make even an excellent estate plan much harder than it needed to be.
Learn more about I Wish I Talked to You Sooner and how to avoid the estate planning mistakes families too often discover when it is already too late.
About the Author
Ilya Lyubimskiy, JD, CPA, is a Colorado estate planning and probate attorney, Certified Public Accountant, and founder of Premier Legacy Law. He is the author of I Wish I Talked to You Sooner: How to Avoid the Worst Estate Planning Mistakes. Through his legal practice, he helps individuals and families navigate estate planning, probate, and trust administration with an emphasis on practical planning and avoiding preventable problems.
