Selecting the people who will act on your behalf when you can no longer do so is one of the most personal and consequential choices you’ll ever make. Whether you are thinking about who to name in your Health Care Proxy, Power of Attorney, Will, or Trust, each decision involves more than simply identifying someone you care about. These roles demand individuals who are capable, trustworthy, and aligned with your values. They will be your voice and steward when you are unable to speak or act for yourself, so careful consideration is essential.
What Makes a Good Fiduciary
At the heart of every fiduciary role is trustworthiness. A fiduciary must act solely in your best interest, without personal gain or bias. This means choosing someone who has demonstrated honesty and reliability in past situations – someone whose word and actions you can count on.
Equally important is organization. Fiduciaries often juggle complicated tasks – handling bank accounts, communicating with lawyers, filing taxes, or making medical decisions. A person who keeps careful records, pays attention to deadlines, and can manage details under pressure is far better suited to these responsibilities than someone who is easily overwhelmed.
Of course, each role necessitates its own consideration when choosing fiduciaries. For example, when choosing who to name in your Health Care Proxy, compassion and composure are essential. A good health care agent will remain calm in a medical crisis, ask the right questions, and make informed decisions with empathy and clarity. The attorney-in-fact named in your Power of Attorney or your Trustee in your Trust, should have good organization skills, attention to detail, and financial literacy. The person doesn’t need to work in the finance field, but they should be comfortable reviewing statements, understanding basic financial principles, and consulting professionals when needed.
Across all these roles, certain qualities rise to the top: organization, honesty, reliability, and good judgment. Yet perhaps the most important trait of all is familiarity with you – the way you think, what you value, and what kind of legacy you want to leave. A fiduciary who knows you deeply is more likely to make choices that reflect your character, even in situations you could not have predicted.
It’s also worth remembering that these appointments are not set in stone. Life changes, and so do relationships. Review your designations every few years, or after major life events, to ensure they still make sense. Discuss your decisions openly with those you appoint so they understand the scope of their responsibilities and the spirit behind them.
Common Mistakes When Choosing Fiduciaries
Despite good intentions, many people make avoidable errors when naming fiduciaries. One of the most frequent mistakes is choosing based on emotion rather than capability. It’s natural to want to appoint a spouse, child, or close friend, but not everyone has the skills or temperament for the role. Affection should be balanced with practical assessment.
Choosing a fiduciary based solely on the birth order of your adult children is another common pitfall. The oldest child may not have the organizational skills, temperament, or availability needed to manage complex financial or legal responsibilities. Age does not necessarily equal capability or good judgment.
Another misstep is failing to discuss the role in advance. A fiduciary who is unaware of their appointment – or unclear about what’s expected – may decline when the time comes, leaving your plans in limbo. Having an open conversation ensures they understand your wishes and are comfortable accepting the responsibility.
Sometimes people overlook potential conflicts among family members when choosing fiduciaries. Naming one child as power of attorney or executor can lead to resentment or disputes among siblings. In families where tensions already exist, a neutral or professional fiduciary may better preserve relationships and ensure fairness. Similarly, naming co-fiduciaries who don’t get along can cause major problems down the road – so much so that some institutions often do not accept co-fiduciaries.
Making Thoughtful Choices
Choosing fiduciaries is ultimately an act of trust. You are entrusting someone to stand in your place when you cannot, to act not only with authority but with heart. By selecting individuals who combine integrity with understanding – people who are both capable and who truly know you – you ensure that your health, your finances, and your legacy are carried forward exactly as you intended.
Attorney Leah A. Kofos is an attorney with the Dedham firm of Samuel, Sayward & Baler LLC, which focuses on advising its clients in the areas of trust and estate planning, estate settlement, and elder law matters. This article is not intended to provide legal advice or create or imply an attorney-client relationship. No information contained herein is a substitute for a personal consultation with an attorney. For more information visit ssbllc.com or call 781-461-1020.
© 2025 Samuel, Sayward & Baler LLC

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