Choosing the Right Executor – One of the Most Important Decisions!
At Wakefield Law, we have heard time and time again that deciding who is executor, trustee, or any other fiduciary is one of the hardest parts of the process. Sometimes it’s even harder to choose backups – who would serve if your primary choice is not around or is incapacitated? When clients sit down to create an estate plan, they tend to focus on the documents themselves—trusts, wills, powers of attorney, and medical directives. These, of course, are vital, but one of the most important decisions in the entire process is often the most underestimated: choosing the right person to serve as your trustee, executor, or agent.
Many people feel pressured to name their oldest child, or for people in their 20s/30s/or 40s, to appoint their parents or siblings because that’s what feels like what they have to do. What’s worse is when parents want to appoint multiple children as co-agents to “keep the peace,” or avoid hurting anyone’s feelings. But these decisions, when made out of obligation rather than practicality, can create far more problems than they prevent.
Why Fiduciary Roles Matter
Trustees, executors, and agents under your Power of Attorney (POA) or Advance Medical Directive (AMD) may need to step into action at life’s most challenging moments—incapacity, medical emergencies, or after death. These roles involve:
Managing finances, property, and investments – acting quickly and with complete competency and integrity
Coordinating tax filings and legal obligations
Communicating with beneficiaries and making sure money is flowing to them as is required in the documents
Making urgent medical decisions in accordance with YOUR WISHES – appointing someone who will keep you alive far past when you would want, or even make rash decisions, is not the right move
Handling complex administrative tasks – even with a well-constructed plan, this stuff can be hard and time-consuming. It needs someone who can fully attend to the process and do it well.
The wrong person in the wrong role can unintentionally create delays, disputes, or financial missteps at precisely the moment when clarity and leadership are most needed.
The Myth of the “Oldest Child Rule”
A surprising number of clients tell us they feel obligated to name their oldest child simply because of birth order. But being the eldest has nothing to do with being prepared, capable, or willing to handle the significant responsibilities of a fiduciary. Sometimes, the youngest child might have the most familiarity with money and other administrative processes like financial planning and tax.
If choosing a child, consider which child has skillsets in the following:
Organized and financially responsible
Comfortable making tough decisions, especially under pressure
Able to communicate clearly and calmly
Geographically close enough to help when needed
Willing to take on the role and handle things fairly
If not, naming them simply because they were “first born” could lead to serious complications.
Why “Co-Everything” Is Often a Mistake
While naming two or more children or family members/friends as co-trustees or co-agents may feel like the fair or diplomatic choice, it can make administration far more complicated. Co-decision-making often means:
Delays when signatures or approvals from both parties are required
Disagreements that stall important actions
Confusion about responsibilities and authority
Strained family relationships at an already stressful time
Unless your chosen co-fiduciaries work exceptionally well together, live near one another, and share similar decision-making styles, two is rarely better than one.
It’s OK—Often Wise—to Choose Someone Outside the Family
For some families, the best fiduciary isn’t a child, sibling, or parent. It might be:
A trusted friend
A more responsible or available relative
A professional fiduciary or corporate trustee
Choosing someone outside the family can avoid emotional tensions, reduce the risk of disputes, and ensure that the person you select is ready and able to act when a crisis occurs. Sometimes, an arms-length agent can handle things better than someone who is too close and who has too much water under the bridge.
We Can Help You Make the Best Choice
At Wakefield Law, we spend lots of time with our clients about choosing the right person, and making sure that person understands the role they are taking on. We often meet with our clients’ agents to discuss what their obligations will be and how they will need to act if something happens.
If you’re uncertain about whom to choose, and that’s holding you back from moving forward, give us a call to see if we can help you make the important decisions to ensure you and your family are protected with a well-written estate plan. 703.771.9740