The Hidden Headaches of Being an Estate Executor

Being named an executor might sound like an honor—distribute assets, file some paperwork, and call it a day, right? Wrong. It’s a job that comes with more complexity, time, and emotional labor than most people realize. If you’re considering saying “yes” to this role (or naming someone in your own estate plan), understanding the realities upfront can save a world of stress.

Now, let’s clear up some terminology. If there’s a will, the person in charge is called an “executor.” If there’s a trust, it’s a “trustee.” And if someone’s alive but incapacitated, the person handling their finances is the “power of attorney.” Same idea, different job titles.

Today, we’re focusing on the executor—the one tasked with following the will’s instructions after someone passes. If you’re curious about trustees, let’s chat. In the meantime, let’s break down what being an executor really means.

When "Executor" Becomes "Expensive"—The Unexpected Financial Burden

One of the biggest surprises for executors? The immediate financial burden. When someone passes away, their accounts are locked tighter than Fort Knox until a court officially appoints an executor. That appointment can take weeks, months, or even longer. And guess who’s left holding the bag in the meantime? Yep, the executor.

Funeral homes and service providers don’t wait for the court process. Most want payment upfront—often $10,000 to $25,000 or more. While the estate can eventually reimburse those costs (if there’s enough money), the executor has to cover it first and wait months for repayment. That’s a tall order if you don’t have that kind of cash just lying around.

But it doesn’t stop there. The executor is also on the hook for property taxes, utility bills, insurance premiums, and maintenance for the deceased’s home. The estate’s assets might be frozen, but the bills keep rolling in. Many executors end up shelling out thousands of dollars from their own pockets during this waiting game, adding financial stress to an already emotional situation.

And here’s the kicker—if the will wasn’t drafted by an experienced estate planning attorney (or worse, was a DIY job), the court might require the executor to post a bond. That’s basically an insurance policy to protect the estate, and it can cost thousands out of pocket before the executor can even start their job.

Bottom line? Without a solid Estate Plan designed to bypass court, you’re not just leaving your executor with responsibilities—you’re leaving them with the bill.

Buried in Paperwork: The Executor’s Paper Chase 

The paperwork involved in serving as an executor? It’s like drowning in a sea of forms, phone calls, and fine print. Executors aren’t just handing out inheritance checks—they’re on the hook for tracking down and organizing every financial account the deceased owned. We’re talking bank accounts, investment portfolios, retirement funds, and insurance policies. And that’s just the start.

First, they’ll need multiple copies of the death certificate (yes, multiple—because every bank, insurance company, and government agency wants their own). Then there’s filing court documents to kick off probate, submitting final tax returns, closing utility accounts, notifying creditors, and processing insurance claims. And don’t be surprised if a financial institution throws in a curveball like requesting a medallion signature—an identity verification process that’s as tedious as it sounds.

The whole ordeal involves endless phone calls, countless trips to banks and courthouses, and hours upon hours of paperwork. Many executors report spending hundreds of hours—sometimes stretching over months or even years—wrangling documents and chasing down details.

But here’s the real kicker: some assets might never be found. If you haven’t meticulously organized your finances and made sure your executor knows exactly what you own and where to find it, those assets could slip through the cracks. And when they do? They don’t magically find their way to your loved ones. Instead, they get turned over to the State’s Department of Unclaimed Property, where they sit until someone—if ever—comes forward with the right documentation to claim them.

Let that sink in. Do you really want your hard-earned money gathering dust in a government account instead of going to your family? If the answer is a hard “no,” then it’s time to get serious about creating an Estate Plan. Because the best way to protect your assets—and your family—is to make sure everything is organized, accounted for, and legally locked down. Keep reading to find out how to get started.

Navigating the Family Drama (Because Let’s Be Honest, There’s Always Some)

Being an executor isn’t just about paperwork—it’s about managing people, emotions, and, let’s be honest, family drama. You’re stuck enforcing the deceased's wishes while everyone else is stuck in their feelings. Siblings start side-eyeing each other, Uncle Bob suddenly remembers a "promise" about the lake house, and you're left playing referee while grieving yourself. It’s exhausting, thankless, and, if not handled carefully, can spark conflicts that turn into full-blown court battles. Trust me, nothing divides a family faster than unclear instructions and unmet expectations. That’s why a solid estate plan isn’t just helpful—it’s essential. 

Set Your Executor Up for Success: What You Can Do Now

When you have a Planning Session with me, we’ll make your executor’s job way easier. I’ll help you build a complete asset inventory—account numbers, passwords, the whole nine yards—so your executor isn’t stuck playing detective. We’ll keep that inventory updated, too, so when the time comes, it’s all right there.

Worried about funeral costs and bills piling up? We’ll plan for that, setting aside funds so your executor doesn’t have to foot the bill while waiting for probate. Speaking of probate—if we use a trust and name your executor as trustee, they can skip the court circus entirely.

We’ll also record a Life & Legacy Interview, making your wishes crystal clear and cutting off family drama before it starts. And let’s be honest—just because someone’s your oldest child or closest sibling doesn’t mean they’re the right fit for this job. I’ll walk you through what the role actually involves, so you can pick the best person for the task, not just the person who feels like the default. Eyes wide open—that’s how we roll. 

How I Help Make Estate Planning Easier (and Way Less Stressful)

Let’s be real—being an executor can be an absolute nightmare if there’s no solid plan in place. But when you work with me at 20West Legal, we’re not leaving your loved ones to figure it out on their own. My Planning Session process makes sure your executor has everything they need, neatly organized and stress-free.

Here’s the deal: I’ll help you create a comprehensive estate plan that covers all the bases—wills, trusts, power of attorney, healthcare directives, and more. No guessing games. No scrambling for passwords. No “Where the heck did Mom keep her life insurance policy?”

But it doesn’t stop there. After you’re gone, I’ll be here to guide your executor through the probate process, handle the legal red tape, mediate any family drama (because, let’s face it, there’s always family drama), and make sure every “i” is dotted and every “t” is crossed.

The best part? This isn’t just for Sudbury locals. If you’re in Metrowest Boston, Maynard, Framingham, Natick, Concord, or any of the nearby towns, I’ve got you covered.

✨ Bottom line: A Planning Session isn’t just about documents—it’s about protecting your family from stress, conflict, and unnecessary court battles. It’s the ultimate “I love you” gift, and it lasts way longer than chocolates or flowers.

Ready to take the first step? Schedule a complimentary 15-minute consultation today, and let’s talk about how to make life easier for the people you love most.

👉 https://go.20westlegal.com/meeting-scheduler

This article is a service of 20WestLegal LLC. We don't just draft documents; we ensure you make informed and empowered decisions about life and death for yourself and the people you love. That's why we offer a Planning Session, during which you will get more financially organized than you've ever been before and make all the best choices for the people you love. You can begin by calling our office in Sudbury, Massachusetts today to schedule an Estate Planning Session and mention this article to find out how to get this $750 session at no charge.

The content is sourced from Personal Family Lawyer® for use by Personal Family Lawyer® firms, a source believed to be providing accurate information. This material was created for educational and informational purposes only and is not intended as ERISA, tax, legal, or investment advice. If you are seeking legal advice specific to your needs, such advice services must be obtained on your own separate from this educational material.