How to Start the Conversation About Estate Planning with Your Parents

Shallon Weis |
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Estate Planning
Family
Health
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Insurance
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Some conversations are simply hard to have.

Bringing up estate planning or long-term care with aging parents can feel uncomfortable, emotional, and deeply personal. But waiting until a crisis hits such as a fall, a diagnosis, or a hospital stay makes things even harder. By then, you’re making decisions under pressure instead of from a place of peace.

At Bradford Financial Center, we’ve seen how proactive planning preserves not only financial stability but also family harmony and lasting legacy. Here’s how to open the conversation with empathy and clarity.

Begin with Empathy, Not Instructions

Parents aren’t checklists or spreadsheets—they’re people with feelings, values, and a lifetime of experiences. When you start the discussion about legacy or estate planning, focus first on understanding what matters most to them.

Instead of jumping straight into “what if” scenarios, begin with questions that honor their independence and dignity.

Try asking: “What would make you feel most comfortable as you age?”
Not: “Have you thought about assisted living yet?”

The first approach invites dialogue. The second can sound like you’ve already decided for them.

Focus on Care, Not Crisis

Estate planning is about love and stewardship. It’s not about expecting loss. When you frame conversations around care and protection, they naturally feel less intimidating.

Try asking: “If one of you needed support, how could we make sure both of you still feel cared for?”
Not: “What happens when one of you passes away?”

This reframes the talk as a collaboration, helping you plan together for comfort, not confrontation.

Acknowledge What’s Already in Place

Only about a quarter of Americans have a will in place, but that doesn’t mean your parents haven’t started thinking about the future. Approach the topic from a place of trust and curiosity.

Try asking: “What plans have you already made to protect your legacy?”
Not: “You don’t have any estate documents, do you?”

This creates an opening for your parents to share their progress, while giving you a clearer view of what steps remain such as updating beneficiaries, adding a healthcare power of attorney, or considering long-term care planning.

Ask About Concerns, Not Conditions

Health changes are hard to talk about. Many people fear being treated differently or losing control if they mention cognitive or physical decline. Instead of focusing on diagnoses, ask about what worries them most.

Try asking: “What concerns you about getting older?”
Not: “Are you afraid of developing dementia?”

You’ll learn what matters most to them—safety, independence, or maintaining a certain lifestyle—which helps guide their estate and legacy planning with compassion.

Offer Support, Not Solutions

These are complex topics, both emotionally and financially. Bringing in a trusted professional can ease tension and provide clarity.

Try asking: “Would you feel more comfortable if we met with a financial advisor together?”
Not: “Don’t you think it’s time to see someone about this?”

At Bradford Financial Center, we regularly help families navigate estate planning, wealth transfer, and legacy protection with objectivity and care. Our advisors act as partners, translating emotion into action and vision into plan.

Bringing It All Together

You don’t need to cover everything in one conversation. Start small, over coffee, a walk, or a family dinner. Ask one question that opens a door, and then listen.

The goal isn’t to have a perfect plan today, it’s to start building one intentionally. When your family’s legacy plan is guided by open communication, sound advice, and shared understanding, everyone can move forward with greater peace of mind.

Conversation Starters for Talking with Parents About Money

Not every financial conversation has to feel heavy. Sometimes, the right question at the right moment opens the door naturally. Try one of these to get started:

  • “I’ve been reviewing my own financial plans, and it made me curious how you approached yours. Would you be open to talking about it?”
  • “If something unexpected happened, how would you want us to handle things? I just want to make sure I understand your wishes.”
  • “What does a comfortable retirement look like for you? Is there anything you’d like to plan for that we could help support?”
  • “Have you thought about how you’d want decisions handled if you couldn’t make them yourself? I want to make sure we know what matters most to you.”
  • “Do you have documents like a will or power of attorney in place? I’m learning how important it is to keep those updated.”
  • “Who helps you with your financial or estate planning? Maybe we could schedule a meeting together to make sure everything is organized.”
  • “If you could leave one lasting lesson or legacy for the family, what would it be?”
At Bradford Financial Center, we help families define and protect their legacy through comprehensive financial and estate planning strategies. Because the best time to plan isn’t during a crisis, it’s while you still have the time, clarity, and connection to make it meaningful.
Sources:
  1. Caring.com, 2025 [URL: https://www.caring.com/resources/wills-survey]
  2. Gerontological Society of America, 2025 [URL: https://doi.org/10.1093/geront/gnae186]

 

Disclosure: This content is developed from sources believed to be providing accurate information. The information provided is not written or intended as tax or legal advice and may not be relied on for purposes of avoiding any Federal tax penalties. Individuals are encouraged to seek advice from their own tax or legal counsel. Individuals involved in the estate planning process should work with an estate planning team, including their own personal legal or tax counsel. Neither the information presented nor any opinion expressed constitutes a representation by us of a specific investment or the purchase or sale of any securities. Asset allocation and diversification do not ensure a profit or protect against loss in declining markets. This material was developed and produced by Advisor Websites to provide information on a topic that may be of interest. Copyright 2025 Advisor Websites.