We often tell our clients that having an estate plan is one of the greatest gifts you can leave behind. But what happens when the plan doesn’t work the way you thought it would?
I recently saw this firsthand when my father served as the Personal Representative — sometimes called an Executor — for a relative’s estate. Different states use different terms, but the role remains the same: this person is legally responsible for settling an estate after someone dies, handling everything from paperwork and taxes to distributing assets to heirs.
While this relative is not a Birchwood client, I believe the story offers meaningful insights into the often-overlooked realities of serving as a Personal Representative (Executor), and I hope it helps others prepare thoughtfully for this role.
Even with my father’s own financial experience and my years of helping clients navigate estate and legacy planning, the process opened our eyes. On paper the plan looked solid. In reality, it became nearly a full-time job.
It Seemed Simple Until It Wasn’t
My dad had agreed years ago to be the Personal Representative (Executor) for his relative, a single woman with no children. She had a will and a trust, and had told him generally what to expect.
But when the time came to settle the estate, things weren’t as clear:
- Some accounts had no beneficiaries listed.
- Assets weren’t properly titled in the name of the trust.
- Vehicles were still titled out of state.
- Documents were missing or outdated.
And this wasn’t a small estate – there were more than 30 beneficiaries, including several charities.
Executor Responsibilities Can Feel Like a Second Job
The process of settling the estate quickly became overwhelming. My dad was investing about 20 hours each week for eight months — and the process is still ongoing. It will likely take three years in total to complete.
The complexity of assets made the job even more demanding. The estate included real estate in multiple states, antiques, jewelry, vehicles, physical stock certificates, safety deposit boxes and more than 30 bequests from the will.
Here’s just a sample of what he faced:
- Travel to out-of-state banks
- Reconstructing multiple years of missing tax returns
- Managing family and beneficiary expectations
- Tracking down paperwork required to transfer stock ownership
- Filing a police report when valuable items went missing from the home
“Obtaining a ‘medallion signature guarantee’ stamp was nearly impossible,” he shared after spending weeks locating an institution to process the paperwork required to transfer stock ownership.
While he was later compensated for his work as Personal Representative, the payment was practical rather than generous. “I didn’t even want the money anymore. I just wanted someone else to do this.”
Common Estate Planning Mistakes
Many of the challenges we faced while settling the estate didn’t come from bad planning, but from incomplete planning.
- Beneficiary designations were missing
- Trust was not fully funded (prior to passing, the trustee must ensure that property and financial accounts are titled or owned in the trust)
- Vehicle and property titles were not updated
- Charitable gifts were scattered across the will rather than in streamlined, tax-efficient accounts
- Codicil (will amendment) was not accepted everywhere — some institutions require an original notarized version
In other words, the paperwork didn’t match the intentions.
Tips to Simplify the Process for Your Personal Representative
After this experience, my parents revisited their estate plan and made big changes — creating a fully funded trust, updating beneficiaries and consolidating their assets. I now use what we learned to help my clients do the same.
Here are a few valuable lessons to simplify your estate:
- Fund the trust. Titling assets is as important as drafting documents.
- Name beneficiaries wherever possible. Transfer on Death (TOD) and Payable on Death (POD) designations can simplify things.
- Convert physical stock certificates to electronic shares. This avoids the need for a medallion signature guarantee and speeds up distribution.
- Consolidate accounts to reduce the number of custodians or institutions involved.
- Stay organized. Keep titles, account information and passwords up-to-date and easy to find.
What to Do If You are Asked to Be a Personal Representative
If you’ve been asked to be a Personal Representative (Executor), keep these things in mind:
- Ask to review the estate plan and trust documents now, not later.
- Check to see that assets are titled properly and beneficiaries are designated.
- Know who the key professionals are — the financial advisor, attorney and CPA will become your key partners.
- Expect the unexpected. Being a Personal Representative (Executor) is a long-term commitment — don’t underestimate the emotional and practical toll.
- If you don’t feel comfortable taking on the responsibilities of a Personal Representative, you can say no (and that’s okay).
Final Thoughts
Serving as a Personal Representative (Executor) is an act of trust, a legal duty, and often a labor of love. But it can also be an emotional and time-consuming responsibility. The process of settling an estate can take years to complete, especially when the estate plan isn’t clear or complete.
I’m proud of how my dad honored his relative’s wishes. But I also know it could have been so much easier. The best gift we can give the people we care about is not just our assets, but an estate plan that’s clear, complete and ready to carry out.
