How To Talk To Aging Parents About Estate Planning

By Kaitlyn P. Tauber, Esq., Liberty Legacy Law Group

Having “the talk” with your parents doesn’t end when you grow up. In fact, one of the most important conversations you’ll ever have as an adult child is about something many families avoid:

Estate planning.

It can feel awkward. It can bring up fear, denial, or painful memories. But it can also build trust, spark connection, and give everyone peace of mind.

As an estate planning attorney, I’ve helped many Maryland families bridge the gap between generations. And as a daughter and granddaughter of hardworking, close-knit people, I understand that these conversations are deeply personal.

This guide is here to help you approach the topic with compassion, clarity, and confidence – no matter where your parents are in their planning journey.

Why This Conversation Matters

When aging parents don’t have a clear estate plan, their children are left to:

• Guess their wishes
• Navigate legal red tape
• Settle family disagreements
• Pay for court costs and delays

The result? Added stress during a time of grief and uncertainty.

It’s not about controlling your parents’ decisions. It’s about protecting their dignity, honoring their choices, and saving your family from unnecessary turmoil later.

Having these conversations ensures that your parents’ values are respected, that their hard-earned assets are preserved, and that your family is not forced into conflict or confusion when emotions are already running high.

When to Start the Conversation

There’s no perfect moment, but here are a few life events that can create a natural opening:

• A parent retiring
• The birth of a grandchild
• A move or downsizing
• A hospitalization or diagnosis
• The loss of a loved one

Still, you don’t need to wait for a crisis. In fact, the best time to talk is when everyone is healthy, stable, and thinking clearly.

Proactive planning avoids reactive decision-making. And it gives your parents the gift of time to reflect on what they truly want.

How to Begin (Without Pressure)

Start with empathy. Here’s how you might open the door:

• “I know this isn’t the easiest topic, but I’ve been thinking about how we can make things easier in the future.”
• “Would you feel comfortable sharing if you have a will or any estate plans in place?”
• “I recently read something about medical directives and it got me thinking… do you have anything like that set up?”

Avoid making it about your inheritance. Focus on their values, protection, and peace of mind.

You might also share your own experience:

• “We just set up guardianship papers for the kids. It made me think about how important it is for everyone to have something in place.”

This helps normalize the topic and reminds them it’s not just about age – it’s about preparation.

Key Topics to Cover

Once the conversation begins, you can gently ask about:

1. Wills and Trusts

Do they have a current will or trust? If not, are they open to creating one? Have they named beneficiaries clearly?

Outdated wills are common and can cause real problems. If a parent created one decades ago, it might name someone who has since passed or no longer reflects their wishes.

Trusts can offer flexibility, privacy, and probate avoidance. This can be especially useful if there is real estate or complicated family dynamics.

2. Powers of Attorney

Who is authorized to make medical or financial decisions if they become unable to?

Who can handle their banking and investments, pay their bills, arrange for their care, coordinate for insurance benefits and do their taxes?

Without a Power of Attorney, you may need to go to court for guardianship, which is time-consuming and emotionally difficult.

3. Advance Medical Directives

Do they have a healthcare proxy, living will or other instructions for medical care?

This document allows them to authorize someone to make medical decisions on their behalf and state their preferences around end-of-life care. It’s a powerful tool for ensuring their wishes are followed, and that their loved ones aren’t left guessing.

4. Asset Organization

Where are key documents located? Have they listed accounts, insurance policies, and property titles?

Helping them organize this information avoids chaos in the event of illness or death. Consider compiling a binder or digital folder that includes:

• Copies of legal documents
• Contact info for financial advisors, attorneys, and insurance agents
• Lists of accounts and passwords

5. Funeral and Burial Wishes

While difficult, this can relieve a huge emotional and financial burden if addressed in advance.

Some families may want to discuss whether they prefer burial or cremation, have prepaid plans, or have special cultural or religious preferences.

What If They’re Resistant?

It’s normal. Many parents fear:

• Loss of control
• Admitting mortality
• Feeling judged or interrogated

If they shut down, try this:

• Back off and revisit later
• Share your own planning efforts first
• Suggest a meeting with a neutral third party (like an attorney)

Remember: the goal is not to rush them into decisions, but to open a door that stays open.

Sometimes, it takes multiple conversations. Let it be a dialogue, not a directive.

Tips for a Productive Conversation

• Pick the right time: Avoid holidays or family gatherings where emotions are high
• Stay calm and respectful: If they get defensive, validate their feelings
• Bring siblings in: If appropriate, include others to prevent future conflict
• Ask open-ended questions: “What do you hope to leave behind?” or “What matters most to you?”
• Keep the focus on them: This is about their legacy and dignity

How We Help at Liberty Legacy Law Group

We understand the family dynamics involved in estate planning. That’s why we:

• Offer family meetings that prioritize respect and privacy
• Explain options in plain language
• Take a collaborative, no-pressure approach
• Customize plans to reflect your parents’ unique values

We don’t just fill out forms. We help families communicate, plan, and protect what matters.

Our experience with Maryland laws and family dynamics allows us to anticipate challenges and guide your parents in making thoughtful, empowered decisions.

Real Peace of Mind Comes from Planning Together

Too many adult children are left in the dark when their parents pass away. They don’t know where documents are. They don’t know the passwords. They don’t know who was named executor or what the burial wishes were.

That uncertainty adds stress to an already painful time.

By helping your parents plan now, you give them:

• Dignity in decision-making
• Confidence that their affairs are in order
• The comfort of knowing their family won’t be left with chaos

And you give yourself:

• Clarity
• Structure
• The ability to grieve and heal without added burdens

Final Thoughts

Talking to aging parents about estate planning isn’t easy. But it’s one of the most loving and practical things you can do.

You’re not being morbid. You’re being wise. You’re showing up for your family – now and in the future.

So when the time feels right, take a deep breath and start the conversation. You don’t need all the answers. You just need the courage to begin.

And if you need a guide, Liberty Legacy Law Group is here to walk that path with you.

Because planning ahead is a gift. Let’s make sure your parents have the legacy they deserve. Contact us!