A client sat in my Manhattan office last week, wrestling with a decision that has kept him up at night for months. He built a successful company from the ground up, and now must decide which of his two children will act as trustee for the other’s share of the inheritance. One is incredibly responsible but emotionally distant; the other is warm and empathetic but has a history of questionable financial choices. “Who do I trust, Russel?” he asked. “It’s not just about who I love. It’s about who can carry this weight.”
His question gets to the heart of what we do. Drafting a will or a trust is a technical exercise. But selecting the people who will execute your wishes—the fiduciaries—is an act of profound trust. A poorly chosen executor or trustee can unravel a lifetime of careful planning and, worse, fracture a family. Over decades of practice, I’ve seen that trust isn’t a feeling; it’s an observable set of characteristics. When I advise families on this choice, we look beyond affection and focus on three distinct qualities.
Demonstrated Judgment Under Pressure
The first quality I look for is a history of sound judgment, especially when life gets complicated. This isn’t about whether someone is a “nice person.” It’s about their ability to remain level-headed and prudent when faced with financial or emotional stress. A fiduciary role is not a reward for being a favorite child or a loyal friend—it is a job with serious legal and financial responsibilities.
Think about the person you are considering. How have they managed their own finances? When they faced a personal or professional crisis, did they act deliberately or impulsively? An executor might have to deal with creditor claims, sell a family home in a down market, or mediate disputes between grieving beneficiaries. A trustee may manage a portfolio for decades, making distributions and investment decisions that will shape a young person’s future. Past performance is the most reliable indicator of future conduct. We need to see a track record of stability and prudence before placing the stewardship of a family’s legacy in their hands.
An Absolute Grasp of Fiduciary Duty
Love and loyalty are not enough. A fiduciary must understand—and be bound by—their legal duty. In New York, this isn’t a vague moral concept; it’s codified in law. For instance, the Prudent Investor Act, found in Estates, Powers and Trusts Law (EPTL) § 11-2.3, requires a trustee to make investment decisions not based on their personal risk tolerance, but on a standard of care that a prudent person would exercise.
This legal obligation is absolute. A fiduciary must always put the interests of the beneficiaries ahead of their own. They cannot co-mingle funds, engage in self-dealing, or favor one beneficiary over another unless the trust document explicitly allows it. This is often the hardest part of the job. It may mean telling a sibling “no” when they ask for an advance on their inheritance to fund a risky business venture. It may mean making a conservative investment choice that a beneficiary disagrees with. The person you choose must have the integrity to uphold this duty, even when it creates personal friction. They are not just a caretaker; they are a custodian bound by law.
The Capacity for Difficult Conversations
Finally, a great fiduciary is a great communicator. They will inevitably have to deliver news that beneficiaries do not want to hear. They will be asked difficult questions about expenses, investment performance, and the timeline for distributions. The person in this role must be able to communicate with clarity, empathy, and firmness.
Consider the family dynamics. If your chosen trustee is intimidated by another beneficiary, or if they avoid conflict at all costs, they will fail. They need the emotional intelligence to explain complex financial matters in simple terms and the strength to hold a boundary when necessary. This is especially critical when a trustee is also a family member. They must be able to transition from their role as a sibling or child to their role as a fiduciary, enforcing the rules of the trust you created. Without this skill, even the best-laid plans can dissolve into suspicion and resentment, often ending up in a contested proceeding in Surrogate’s Court.
Choosing your fiduciaries is arguably the most important decision in your entire estate plan. It’s about appointing a steward for your legacy. The wrong choice can be undone, but often only through costly and painful litigation. The right choice allows your plan to function as you intended, providing for the people you love for generations to come.
Before you put a name in that critical box on your will or trust, the next step should be a candid conversation about the real-world pressures that person will face. If you are a client of our firm, we can schedule a confidential discussion to map out the specific duties and potential conflicts your chosen fiduciary will encounter.
