How to Choose the Right Executor and Trustee

Choosing an executor, trustee and power of attorney: why it matters

Selecting someone to handle your finances, estate or medical decisions may be one of the most important — and overlooked — parts of financial planning. Choosing an executor, trustee and power of attorney affects not just how assets are managed and distributed, but also how smoothly your affairs are handled during periods of incapacity or after death.

As families become more complex, the decision is often far from straightforward.

According to Harry Margolis, many people underestimate the difficulty of naming the right person for these roles. The responsibilities differ significantly, and the wrong choice can create friction, delays or even conflict.

What changed, who is affected and why it matters

More households today face nontraditional family structures, geographic dispersion and longer lifespans. That makes choosing an executor, trustee and power of attorney more complicated than in the past.

Anyone creating or updating an estate plan is affected — particularly those without a spouse, those with complex family dynamics or those relying on friends rather than family.

The financial implications are significant:

A poorly chosen executor can delay asset distribution
An inexperienced trustee can mismanage long-term investments
A weak power of attorney can create gaps in decision-making during incapacity

What this means for you

You do not need to name the same person for every role.

Instead, think of each responsibility separately and match the role to the person best suited to handle it.

The three roles — and how they differ

Margolis emphasizes that executor, trustee and power of attorney are distinct roles with very different demands.

Executor (personal representative): Handles affairs after death. This is an intensive but temporary role, often lasting about a year. Responsibilities include managing probate, paying bills and distributing assets.
Trustee: Manages assets over time, sometimes for years or decades. This role requires ongoing oversight, investment judgment and consistency.
Power of attorney: Typically a standby role. It may never be used, but if activated, it involves managing financial matters during incapacity.

Each role requires a different combination of skills, availability and temperament.

Why one person may not fit every role

In many cases, the same person is not the best choice for all three roles.

A child who lives nearby may be ideal as a power of attorney, able to respond quickly in an emergency. But that same person may not have the time or expertise to manage probate or oversee a long-term trust.

Geography, financial knowledge and personal dynamics all play a role.

Family relationships can further complicate decisions. Naming multiple children can create conflict if they do not work well together. Naming one child over others can lead to resentment.

When to consider professionals

For some responsibilities, bringing in a professional may be the better choice.

Estate planning attorneys may serve as trustees or co-trustees and can sometimes act as executors. Pairing a professional with a family member can provide both technical expertise and personal understanding.

This approach can be especially helpful when family members are willing but not fully equipped to handle the responsibilities alone.

The challenge of health care decisions

Choosing a health care proxy or health care power of attorney is often more personal and complex.

Professionals generally avoid these roles, which means individuals must rely on family members or close friends. As people age, those candidates may face their own health limitations.

That makes it important to revisit these decisions regularly and name backup options when possible.

How to choose the right person

There is no perfect checklist, but the key traits are clear.

Look for someone who is:

Reliable and organized
Able to follow through on commitments
Comfortable handling financial responsibility
Capable of making difficult decisions under pressure

For trustee roles, naming a co-trustee can provide an opportunity to evaluate how someone handles the responsibility and whether they understand your long-term goals.