Beyond the Will: The Conversations That Matter Most

In 42 years of marriage, Bill andLeslie overhauled their estate planningdocuments three times—most recently in the summer of 2025. Each time, they felt the weight of it: the volume of documents, the need to understand their purpose, and the emotional decisions involved.

Editor’s Note: This story originally appeared in North Shore Senior Center’s Engage Magazine and Lifelong Learning Catalog, September-December 2026 issue. It is accessible at this link: Lifelong Learning • North Shore Senior Center

"One crucial step remained," Bill said. "We felt strongly that our son and daughter needed to understand what these documents would mean for them and our grandchildren.

"There were a few tense moments—but our children couldn't have been more appreciative.

“They asked questions, shared some dark humor, and expressed feeling a profound sense of relief and understanding about our wishes. They were so glad we shared.”

Creating a will, trust, power of attorney, and healthcare directive are the building blocks of any solid estate plan. But according to Matt Margolis, an attorney specializing in estate planning and elder law at Margolis Weldon, LLC in Park Ridge, the process is not finished until your family understands the documents and your reasons for making decisions.

Matt identified some of the key questions to ask and issues of personal concern to discuss when embarking on the estate planning process:

CHOOSING YOUR EXECUTOR & TRUSTEES

What qualities should I look for when naming an executor, trustee, or power

of attorney?

I tell clients that choosing a power of attorney for property, trustee, and executor is about choosing someone who is good at running a household. Clients often feel like it must be their son who is a CPA or their daughter who is an attorney.

I remind them that their selections do not need to be professionals. We are looking for people who can pay bills, stay organized, work with tax preparers, and coordinate with other professionals.

Sometimes the child with the most demanding career is not the best choice simply because they do not have the time.

For one’s healthcare power of attorney, the key is choosing someone who is comfortable making tough decisions, especially around end-of-life care. No matter the role, I always recommend clients talk to the person first to make sure they are willing to serve.

It is common for clients to struggle with naming someone. I am often asked if I will serve in one of these roles, and I decline. It is rare for an attorney who prepares an estate plan to also serve as trustee, executor, or power of attorney.

That said, there are plenty of professional and corporate fiduciaries who can step in when needed.

What happens if my named executor or trustee is unable to serve?

There is always the possibility that the person named cannot serve when the time comes, which is why backups are so important. I tell clients, “the more the merrier,” if the people named are trustworthy. I would rather see five successors listed and never need them than only two who cannot step in when needed.

I also tell clients to be selfish when making these decisions. They should choose the right people for the job, not just name someone to avoid hurt feelings. These roles can be time-consuming and, at times, thankless.

PLANNING FOR FAMILY

How do I plan for adult children, minor children, or grandchildren—and which documents cover each?

When I talk to younger clients, most of them are motivated by wanting a plan in place for their children. Guardians for minor children are named in a last will and testament and are included, whether the plan is will-based or trust-based.

Whether a client has a will or a revocable trust, we always discuss how assets should be distributed. Factors like age, responsibility, and potential special needs matter.

In many cases, a trust is the best way to manage distributions, especially when you want to avoid giving assets outright to younger or less financially responsible beneficiaries, or to protect eligibility for needs-based benefits.

Is it easy to name other beneficiaries such as organizations and causes?

Clients can name charitable organizations as beneficiaries. When they do, I recommend contacting the organization to make sure we are using the correct language, so the gift is used as intended.

TALKING TO YOUR FAMILY

What is the best way to walk family members through documents, key decision-makers, and end-of-life wishes?

When it comes to sharing estate planning documents, every client is different. I usually recommend sharing documents with key people. But if the client is uncomfortable, I suggest they share my contact information, so the right people know who to call when the time comes.

What final steps are needed?

One area that often gets overlooked is trust funding. Signing the documents is not the finish line. While attorneys often help retitle real estate, clients still need to update bank accounts, investment accounts, and beneficiary designations to be transferred to the trust, rather than an individual.

Many people create trusts to avoid probate but if the trust is not properly funded, probate may still be required, and by then it is too late to fix it.

Avoid Blindsiding Your Family

Bill and Leslie’s experience highlights a step that is often overlooked but can make all the difference: having the conversation. Estate planning is not just about signing documents; it is about preparing the people who will one day carry out those plans.

When children and other trusted individuals are included in the discussion, it provides transparency around roles, expectations, and the reasoning behind key decisions.

This can reduce the risk of conflict and prevent confusion and the feeling of being blindsided during an already emotional time.

In the end, a well-communicated plan does more than distribute assets. It allows the estate administration process to move forward with greater ease and harmony.

About North Shore Senior Center

Headquartered in Northfield, NSSC is a nationally accredited 501(c)(3) organization that serves older adults whether they are fully independent or in need of additional support.

Offering a wide range of services including memory care programs, educational classes, and wellness activities, NSSC provides a welcoming space to connect, learn, and build community. NSSC is open Monday through Friday from 9 a.m. to 5 p.m. To learn more, stop by NSSC located at 161 Northfield Road, Northfield, IL, or visit nssc.org.