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What happens when the person you trusted to carry out your wishes is not up to the task? This question is one many families do not consider until it is too late. In the previous article, we emphasized how staying organized can ease the burden of estate administration. But even the most well-organized plan can unravel if the wrong person is at the helm. The role of an executor or trustee is more than ceremonial. It comes with legal, financial, and emotional responsibility. When that responsibility is mishandled or unwanted, the consequences can be far-reaching. Whether it is missed deadlines, mismanaged assets, strained family relationships, or even legal disputes, a poorly chosen executor can create unnecessary complications and lasting damage. In this article, we will explore real-world risks, red flags to watch for, and practical steps you can take today to help ensure your legacy is carried out by someone capable, trustworthy, and prepared.
Before we get started, the purpose of this article is not to create fear, it is to create clarity.
It is a difficult truth, but one worth acknowledging: just because someone loves you does not mean they are the right person to settle your estate. Often, individuals name a spouse, an adult child, or close friend as executor out of familiarity or a sense of obligation without fully considering the demands of the role. Administering an estate requires more than good intentions. It takes patience, attention to detail, and the ability to communicate clearly and calmly with all parties during an emotionally charged time.
We have seen firsthand how executors can become over whelmed and allow family dynamics to interfere with sound decision-making. Sometimes the result is unintentional conflict; in other cases, poor choices lead to delays, legal complications, or financial consequences that could have been prevented with the right preparation. Examples of these results could include loss of assets, years of legal issues, and family issues that could last a lifetime. These are the very reasons that having a corporate trustee is very helpful.
So, what makes a good executor? At the most basic level, it starts with integrity and trust, but it does not end there. A good executor is someone who can remain calm under pressure, is organized enough to manage deadlines and paperwork, and communicates clearly with attorneys, accountants, and beneficiaries alike. They do not need to be a financial expert, but they do need to be dependable, attentive, and capable of making decisions without letting personal feelings get in the way.
It is important to look beyond relationships and ask: Would this person be willing and able to navigate a process that could take months or even years to complete? Will they be objective when emotions run high? Will they understand their duty to follow your instructions exactly as written, even when others may question them? Will they understand that their duty takes time, effort, and patience? These are not easy responsibilities, and many people underestimate just how involved the role can become until it is already too late.
We encourage clients to think practically, not sentimentally, when choosing an executor. It is natural to want to name someone close to you, but closeness alone does not prepare someone for the job. In fact, it can sometimes complicate things, especially if that person is grieving, unfamiliar with financial matters, or caught in the middle of family tension. Choosing someone who can lead with clarity, steadiness, and respect for the process is one of the best decisions you can make for your legacy.
Availability is another key factor. Being an executor is not something that can be done casually or from a distance. If someone is already stretched thin with work, lives far away, or simply is not detail-oriented, that can become a real obstacle, especially when deadlines, forms, and family expectations start piling up. While it is natural to want to choose someone close, it is important to consider how personal relationships might affect their ability to lead. When there are complex distributions or sensitive family dynamics involved, putting a sibling or adult child in charge can sometimes do more harm than good. What you need is calm, clarity, and fairness, not just familiarity.
Choosing the right executor is one of the most important decisions a person can make when planning their estate. It ensures that intentions are carried out clearly and that loved ones are spared the added burden of confusion or conflict. Looking ahead, the conversation does not end with who manages the estate, it naturally leads to those who will inherit it. The next article in this series will explore what it means to transition generational wealth responsibly: not just passing down assets but preparing the next generation to receive them with clarity, maturity, and purpose.