People spend a lot of energy deciding what their estate plan says — who gets the house, how the accounts are split, what happens to the business. That's important. But I've watched solid plans go sideways for a different reason: the documents were fine, and the people chosen to carry them out were the wrong fit. Your plan is only as good as the team you put behind it.
By "team," I don't mean my office or any law firm's staff. I mean the people you choose to step in and act — for you while you're alive but unable, and for your loved ones after you're gone. Picking those people well is one of the most consequential decisions in the whole process. Let me walk you through the key roles.
Your Executor
Your executor (Illinois often calls this person a representative) is the one who carries your will through probate — gathering your assets, paying your final bills and taxes, and distributing what's left according to your wishes. It's a real job with real deadlines and real paperwork.
The instinct is to name your oldest child, or whoever you're closest to. Sometimes that's right. But the better question is: who's organized, level-headed, and trustworthy with money? Who can stay calm when siblings disagree? Geography helps too — an executor across the country can manage, but a local one has an easier time. Choose the person who can actually do the work, not just the one whose feelings you're most worried about.
Your Trustee
If your plan includes a trust, your trustee manages and distributes those assets under the terms you set — sometimes for years, especially if you're providing for young children or a beneficiary who needs ongoing support. This is a long-haul role.
A good trustee is responsible with money, even-handed among beneficiaries, and willing to follow your instructions even when a beneficiary leans on them to do otherwise. For complex situations — a sizable trust, a special-needs beneficiary, or family tension — a professional or corporate trustee is worth considering. There's nothing wrong with naming a bank's trust department or a trusted professional instead of putting that weight on a family member. Ongoing trust administration is exactly the kind of work that benefits from steady, neutral hands.
Your Agents Under Powers of Attorney
These are the people who act for you while you're still alive but can't act for yourself — and they're the part of the team people overlook most.
- Your agent under a power of attorney for property handles your finances if you're incapacitated: paying bills, managing accounts, dealing with your home. This person needs your complete trust, because the authority is broad.
- Your agent under a power of attorney for health care makes medical decisions when you can't, guided by the wishes you've expressed. Name someone who will honor your preferences, not substitute their own, and who can hold steady under pressure in a hospital hallway.
Without these documents in place, your family may have to go to court for guardianship to do things you could have authorized with a signature. That's a slow, public, expensive detour you can spare them.
Guardians for Minor Children
If you have young children, this is the most important name in the entire plan — and often the hardest. Your guardian is who raises your kids if you and the other parent can't. I've seen parents put off their whole estate plan because they couldn't agree on this one choice. Don't let it freeze you. An imperfect choice you've actually made is far better than leaving it to a judge who never met your family. Think about values, stability, and who your children already know and love. And once you've chosen, name a backup too.
The Professionals Around You
Beyond the fiduciaries you appoint, most families are well served by a small bench of advisors working together:
- An estate planning attorney to build the plan, keep it current as the law and your life change, and guide your family through administration later.
- A CPA or tax professional for income, gift, and estate tax questions — and there can be real tax consequences in how a plan is structured and carried out.
- A financial advisor to align your investments and beneficiary designations with the plan, so everything pulls in the same direction.
The best outcomes I see come when these advisors actually talk to one another instead of working in silos. Coordination is half the value.
Common Mistakes With Your Team
A few patterns come up again and again:
- Naming someone out of obligation. Birth order and feelings are not job qualifications. Pick capability.
- Never naming a backup. People decline, move away, or pass before you. Always name an alternate for every role.
- Set it and forget it. The person who was right ten years ago may not be right today. Relationships change, people age, life shifts. Revisit your choices.
- Not telling anyone. Let the people you've chosen know, so they're not blindsided — and so they can decline if it's truly not for them.
Let's Build Your Team
A great estate plan is part document, part people. Get the people right, and the documents do what you intended. Get them wrong, and even a beautifully drafted plan can stall. We'll talk through each role, weigh the candidates honestly, and make sure the team you name is one that can actually carry your wishes across the finish line.
If you're not sure who belongs on your team — or whether the people you named years ago are still the right ones — let's sit down and sort it out.