If you have never been asked—or told—that you will serve as a trustee, you may not realize that the request often marks the beginning of one of the most frustrating and underappreciated roles a person can assume. Serving as a trustee is rarely viewed as a job at all, yet it carries significant responsibility, personal risk, and emotional strain. Don’t believe me. This article by James L. Cunningham Jr., Esq. Founder, CunninghamLegal TRUSTEE RISKS AND TRAPS: HOW TO AVOID BEING SUED OR EVEN JAILED should be a must read for anyone who thinks becoming a trustee is an honor or privilege.
In many families, the trustee role is assigned to a family member based on perceived reliability, past success, or familiarity with financial matters. Sometimes the decision is less rational and more emotional—guided by family dynamics, tradition, or favoritism.
The assumption is that someone who is “good with responsibility” will naturally be able to manage a trust.
There is no career path to prepare you for becoming a trustee
This decision typically begins during the estate planning process, when parents complete intake forms with their attorney and encounter the question: Who should serve as trustee? The answer often comes quickly and casually. One child, Sally is seen as dependable and accomplished. Another child Greg may be older but less settled and stable. A third child Bobby who is the “baby’ of the family may be chosen simply because of emotional closeness or convenience. Rarely does the discussion focus on what the role of trustee actually entails. What does it mean to be a trustee?
What is often overlooked is that appointing a trustee is not a symbolic gesture—it is the assignment of a demanding fiduciary role. This assumes the trustee is even aware of those demands. If the trustee is ignorant to the role, then chaos is just a matter of time.
Using the example above, selecting the child based on emotional closeness as trustee may feel reasonable at the time, but it can quietly set the stage for future conflict. There is no career path that truly prepares someone for “this”—for navigating legal obligations, financial decisions, beneficiary expectations, and family tensions all at once.
Trustees are rarely trained or qualified for the role in any formal sense. Most step into the position with little guidance and even less appreciation for the complexity involved. And when family dynamics are already strained, those same tensions do not disappear when a trust is created. Instead, they often intensify, with the trustee caught squarely in the middle.
Being a trustee is not simply an administrative task. It is a role that combines responsibility, judgment, and accountability—often without thanks, appreciation, and frequently with personal risk. Understanding that reality is essential before anyone accepts the job. The trustee is essentially working for the benefit of others only to be underappreciated.
Relief for Trustees Lies Within the Trust, Your Actions, and Professional Guidance
Living trusts are intentionally designed to assign roles, establish rules, and give ongoing voice to the trustor’s intentions—carried out through the trustee. When the trustor is no longer able to make decisions, the trustee’s role becomes both essential and, at times, subject to scrutiny.
The trust document itself should serve as the trustee’s primary guide when making difficult or consequential decisions. It is meant to provide direction, define authority, and set boundaries that align with the trustor’s values and objectives. In effect, the trustee is not acting on personal preference, but on behalf of the trustor’s expressed wishes. Trustees should read the trust document carefully and seek clarification from the professionals who drafted it, as well as from the trustors themselves, while the trustors are still able to participate in those discussions. Having these conversations early can provide valuable context and reduce uncertainty when decisions must later be made independently.
In addition, trustees should develop a disciplined system for documenting decisions, including the rationale behind them.
Maintaining contemporaneous notes and records can be invaluable if decisions are later questioned or if tensions among beneficiaries begin to surface. Clear documentation helps demonstrate thoughtful, good-faith administration of the trust and can serve as an important safeguard for the trustee.
Using the earlier example, if the parents were conservative in their investment philosophy, the trustee is expected to manage trust assets with the same mindset. Similarly, if both parents are residing in assisted living and the family home is no longer in use, the trustee may be required to decide whether selling the property or retaining it as a rental best serves the trust’s purpose. These decisions are rarely simple and often invite differing opinions from beneficiaries.
In such moments, trustees find relief not only in the guidance provided by the trust itself, but also in the support of experienced professionals who can help interpret responsibilities, manage risk, and navigate complex choices with confidence.
Further relief by hiring a Trustee Service might be the better alternative
Fortunately, many trustors and trustees have the option of appointing a corporate trustee rather than relying on a family member. This approach can significantly reduce personal strain by shifting the responsibility for decision-making and administration to a professional firm experienced in trust management.
By engaging a corporate trustee, families can relieve individual family members from the burden of navigating complex fiduciary decisions, managing assets, and mediating beneficiary expectations. Instead, these responsibilities are handled by an institution with established processes, internal controls, and fiduciary expertise.
Industry sources generally indicate that professional trustee services cost between 1% and 2% of the assets held in the trust, depending on complexity and scope. If the trust is valued at $1,000,000, then is paying $10,000 to $20,000 per year worth may or may not be worth that expense. While this represents an ongoing expense, many families might find the cost worthwhile to prevent family tensions from intensifying and to preserve personal relationships over time.
The trustee is the center of decisions and family issues
Serving as a trustee is rarely a role people seek out, yet it carries significant responsibility, emotional complexity, and personal exposure. What often begins as a well-intentioned family decision can quickly become a demanding and thankless obligation—one that places the trustee at the center of financial decisions, beneficiary expectations, and long-standing family dynamics.
Whether a trust is administered by a family member or a professional trustee, the risks are real and should not be underestimated. Clear trust provisions, thoughtful planning, and the involvement of experienced professionals can help trustees navigate their duties more effectively. Some of that planning might include adding trustee insurance to protect the trustee from personal liability. Just as importantly, trustees should recognize the value of protecting themselves as they carry out these responsibilities.
Understanding the realities of the trustee role—and planning accordingly—can help preserve both family relationships and personal peace of mind.
J.B. Woods is the founder of Greenpoint Insurance Advisors, LLC, an independent insurance brokerage specializing in trustee liability insurance for living trusts. Licensed since 2009, he has extensive experience advising clients on complex liability exposures, insurance procurement, and fiduciary risk. His work focuses on helping trustees understand their responsibilities, evaluate trust-related risks, and obtain insurance designed to protect them in their fiduciary capacity.
The author does not provide legal or tax advice. Coverage availability and policy terms vary by insurer and jurisdiction.