Sarah Henderson thought she had everything figured out. At 58, she'd finally gotten around to writing a will after her husband Mike's mild heart attack last year. She named their eldest daughter, Jessica, as executor because, well, Jessica was the "responsible one" – you know, the daughter who actually returns phone calls and remembers birthdays.

What Sarah didn't know was that Jessica lived in a different state, had never handled anything more complex than her own mortgage paperwork, and was currently going through a messy divorce. Oh, and did we mention Jessica and her brother Tom haven't spoken since the Great Thanksgiving Turkey Incident of 2019?

Fast-forward eighteen months. Sarah passes unexpectedly, and Jessica finds herself trying to navigate probate court via Zoom calls between her own custody hearings, while Tom threatens to contest everything because he's convinced Jessica is "playing favorites" with their mother's jewelry distribution.

Meanwhile, Uncle Bob – Sarah's brother who always "knew about money stuff" – keeps calling Jessica every other day asking why she hasn't liquidated Sarah's investment accounts yet, apparently unaware that freezing and distributing assets isn't quite as simple as transferring a Venmo payment.

Sound familiar? Welcome to the wonderful world of estate execution gone wrong.

Think of an estate executor as the person who gets to play cleanup crew after the final curtain call. They're legally responsible for gathering assets, paying debts, filing tax returns, and distributing what's left according to your wishes. It's like being a project manager, accountant, detective, and family therapist all rolled into one thankless job that pays exactly nothing and comes with a side of potential lawsuits.

The executor handles everything from canceling your Netflix subscription to selling your house. They'll spend months dealing with banks, insurance companies, and government agencies – all of whom will require death certificates, notarized forms, and the patience of a saint.

Oh, and here's the kicker: if you don't name an executor, the court will appoint one for you. Nothing says "I love my family" like letting a judge who's never met any of you decide who gets to make all the important decisions about your stuff.

Here's where things get really fun. Choosing an executor isn't just about picking someone who's good with paperwork – though that helps. It's about understanding the complex web of family relationships, personalities, and potential conflicts that will inevitably surface when emotions are high and money is involved.

The Geographic Challenge: Your daughter in Seattle might be incredibly capable, but if your assets are in Florida, she'll be making a lot of expensive trips or trying to handle everything remotely. Some states require executors to be residents, adding another layer of complexity.

The Sibling Situation: Naming one child as executor while the others inherit equally can create instant resentment. The executor sibling often feels burdened and unappreciated, while the others may view every decision with suspicion. "Why did Mom trust HER with everything?"

The Capability Question: Your eldest son might be a heart surgeon, but can he figure out how to transfer a car title? Some of the most successful people fall apart when faced with bureaucratic processes outside their expertise.

The Availability Reality: That successful corporate executive you're considering? They might not have six months to a year to dedicate to settling your estate, especially while they're also grieving.

Some families opt for professional executors – attorneys, accountants, or trust companies who handle estate administration as their day job. The pros? They know the process, have no emotional investment in family drama, and won't take it personally when beneficiaries get cranky about the timeline.

The cons? They charge fees (typically 2-5% of the estate value), don't have personal knowledge of your family dynamics or wishes, and might handle your estate like just another file on the desk.

Many families find a middle ground: naming a family member as executor but building in professional help through the will, either by explicitly authorizing the executor to hire attorneys and accountants, or by naming a professional as co-executor.

The "I'll Just Name Two People" Trap: Co-executors can work, but only if they're guaranteed to agree on everything. Otherwise, you've just created a recipe for deadlock. Every decision requires consensus, and if they disagree, it's back to court.

The "My Spouse Will Handle Everything" Assumption: If you and your spouse die together (car accident, natural disaster, vacation gone wrong), who's your backup? And backup to the backup?

The "I Don't Want to Burden Anyone" Avoidance: Not choosing anyone is actually the biggest burden of all. Court-appointed administrators are expensive, impersonal, and have no insight into your family's needs or wishes.

The Age Trap: Your 75-year-old brother might be trustworthy and local, but will he be up for the physical and mental demands of estate administration in five or ten years?

Before you make this decision, have some honest conversations:

Your chosen executor will need access to important documents and information. This means creating a system that's more sophisticated than a shoebox under the bed or a "very safe place" that no one else knows about.

Your executor needs to know where to find your will, insurance policies, bank accounts, investment statements, property deeds, and digital account information. They'll need contact information for your attorney, accountant, financial advisor, and insurance agents.

Consider creating a letter of instruction – an informal document that explains your wishes for things not covered in the will, like who should get the family photos, how to care for pets, or what to do with your business.

Once you've made your decision, make sure it's properly documented in your will. Simply telling someone they're your executor isn't enough – it needs to be in writing and properly witnessed according to your state's requirements.

Consider discussing your choice with other family members before you die. This isn't about getting their approval, but it can help prevent surprises and resentment later. Explain your reasoning: "I chose Jessica because she lives nearby and has experience managing Dad's estate, but I want everyone to know that this doesn't reflect how much I love or trust each of you."

Choosing an estate executor is one of those decisions that reveals just how complicated family relationships really are. There's no perfect choice, but there are definitely wrong ones. The goal isn't to find someone who will make everyone happy – that person doesn't exist. The goal is to find someone who will carry out your wishes efficiently and fairly, even when it's difficult.

Remember: this is a gift you give to your family. Not the burden of being executor, but the gift of having someone you trust in charge instead of leaving it to chance, courts, or family arguments.

Your executor doesn't need to be perfect. They just need to be trustworthy, reasonably organized, and willing to ask for help when they need it. Most importantly, they need to understand that their job isn't to make everyone happy – it's to honor your wishes and close out your affairs with as little drama as possible.

So, back to our original question: Have you selected an executor of your estate? If not, what are you waiting for? Another family gathering where everyone gets along perfectly?

Good luck with that.

Ready to tackle this decision head-on? Download our Estate Executor Selection Checklist below to walk through the key considerations and have those important conversations with your family – before they become emergency decisions.