The Executor's Role: Navigating the Hidden Challenges of Settling an Estate
When someone asks you to be the executor of their estate, it might seem like a straightforward responsibility—distribute assets according to their will and handle some paperwork. However, many executors quickly discover that the role involves far more complexity, time, and emotional labor than expected. Understanding these challenges now can help you better prepare, whether you’re creating your estate plan or considering serving as an executor.
Understanding the Executor’s Role
Before we dive in, let’s clarify some key terminology. If someone creates a will, the person responsible for handling the estate is called an executor (or personal representative). If they create a trust, that person is a trustee. If someone becomes incapacitated, the person managing their financial affairs is their power of attorney. While these roles share similarities, they are not identical. This article focuses on the executor’s role—managing an estate after someone has passed. If you’d like more details on trustees or powers of attorney, I’d be happy to discuss them in a consultation.
The Unexpected Financial Burden
One of the most surprising aspects of being an executor is the immediate financial responsibility. When a person dies, their assets are typically frozen until a court grants legal authority to the executor, which can take weeks, months, or even years. In the meantime, many expenses—like funeral costs, mortgage payments, or utility bills—still need to be covered.
Take Michael, for example. When his mother passed away, he assumed he could use her bank account to pay for funeral expenses. Instead, he learned that the account was locked, and he had to cover the $15,000 funeral cost out of pocket while waiting months for reimbursement from the estate. For many families, this financial strain can add another layer of stress during an already difficult time.
Beyond funeral costs, executors often find themselves paying for property taxes, homeowner’s insurance, or even legal fees to initiate the probate process. And depending on the terms of the will, an executor may need to pay for a bond (like an insurance policy required by the court) before being formally appointed—another unexpected and sometimes costly expense.
Drowning in Documentation
The paperwork involved in being an executor can be overwhelming. Executors must track down and organize all financial accounts—bank accounts, investment portfolios, retirement funds, and insurance policies—often without a clear roadmap of what exists.
I remember working with Linda, who spent weeks trying to locate her father’s life insurance policy. She was sure he had one, but she had no idea which company it was with or where the paperwork was stored. She called multiple insurance providers, searched through boxes of old files, and even checked the state's unclaimed property database. Eventually, she found it—months later—but the delay could have been avoided if her father had kept an updated list of his assets.
Executors also need to:
Obtain multiple death certificates;
File court documents to initiate probate;
Submit final tax returns;
Notify creditors and close accounts; and
Process insurance claims.
Some financial institutions require a medallion signature guarantee (a special security measure), which can take even more time. Many executors report spending hundreds of hours over many months just managing the administrative side of an estate.
Navigating Family Dynamics
While handling the legal and financial aspects is difficult, the emotional and interpersonal challenges can be even harder. Executors often find themselves caught between grieving family members, some of whom may have differing interpretations of the will or conflicting expectations.
Sarah was named executor of her father’s estate, but tensions quickly escalated when her siblings disagreed over how personal belongings should be divided. What should have been a simple process turned into months of emotional strain, as she found herself mediating disputes while trying to fulfill her father’s wishes. Family conflict is one of the most common and heartbreaking challenges executors face, sometimes leading to long and expensive legal battles.
How You Can Support Your Executor
If you’re creating your estate plan, you have the power to make your executor’s job easier. A well-prepared plan can prevent financial strain, cut down on paperwork, and minimize family disputes.
When you create a Life & Legacy Plan with me, we take proactive steps to:
Create a clear and organized inventory of your assets—including account numbers, insurance policies, and passwords—so nothing is lost.
Set aside funds for immediate expenses, so your executor isn’t paying out of pocket.
Consider using a trust to bypass probate entirely, giving your executor immediate access to manage assets without court involvement.
Record a Life & Legacy Interview to document your wishes and personal messages for loved ones—helping prevent future misunderstandings.
Carefully select the right person as your executor, based on their ability to handle the role rather than defaulting to the closest relative.
How I Can Help
As an estate planning attorney, my role isn’t just to create documents—it’s to ensure your estate plan actually works when your family needs it most.
If you want to ensure your family is fully prepared, schedule a complimentary 15-minute consultation today.