Editor's note: This is part four of a four-part series on financial conversations. Read the first, second and third articles in the series.
As America's population ages, families face a sensitive yet critical task: discussing finances with older parents. From estate plans and healthcare costs to long-term financial intentions, these conversations can provide much-needed clarity and security.
However, for many families, talking about money and future plans feels daunting. To make this conversation easier, we asked Megan Hughes, managing director of family office services with BOK Financial®, to provide five essential questions that you can use to guide a supportive and respectful discussion about your parents' financial plans.
1. Where do you keep important financial and legal documents?
A crucial first step is understanding where key documents are stored. Knowing where to find wills, powers of attorney, insurance policies and account information can be essential if you need to act quickly in an emergency.
Tip: Approach this question as a way to support your parents’ wishes, not take over their affairs. A phrase like, "In case something happens, I want to make sure we have everything organized just as you'd like," can set a positive tone.
2. Who are your trusted advisors?
Knowing if your parents work with financial professionals—such as attorneys, financial planners, or accountants—can be invaluable. These advisors are often well-versed in guiding families through challenging conversations about finances and may already be encouraging your parents to speak with their children about their plans.
Meeting with your parents' advisor together also can provide a neutral setting to discuss their financial situation and help you gain clarity on their overall goals and wishes.
Tip: Approach this by asking, "Who do you turn to when you need financial or legal advice?" You may even want to suggest, "Would it be helpful if we met with your advisor together to get a sense of your plans?" This shows respect for their judgment while gently opening the door to ongoing communication.
3. Have you considered your healthcare and long-term care needs?
With longer lives come higher costs; you'll need to ensure your parents' finances can keep pace. The average cost of assisted living in the U.S. is around $4,500 per month, and Medicare and Medicaid do not cover room and board. Without a full understanding of your parent's financial resources, you may find yourself in a difficult situation if they need care unexpectedly.
"Without knowing what you're working with, it's hard to start planning," Hughes said. "Are you looking at having to provide in-home caregivers or will your parents need a basic nursing facility? There's a big difference and knowing their financial picture can make planning much easier."
Tip: Ask this question as a gentle inquiry into their preferences. "What type of care would you be most comfortable with, should you need it?" This open-ended question allows them to express their preferences without pressure.
4. What would you like me to know about your inheritance plans?
Perhaps the most avoided topic is the one that's imperative to ask your parents about most: their estate plan, including how they intend to leave their assets. Hughes stressed the importance of transparency when discussing this matter.
"Without prior conversations, an unexpected inheritance can create hurt feelings if expectations aren’t met or leave someone feeling overwhelmed and unprepared to manage a large sum,” she said. “Some inheritors may overspend without guidance, while others hold back, worried about honoring their parents' intentions."
Tip: Frame this question around legacy. "What would you like us to know about the values and decisions behind the assets you're passing down?" This invites your parents to share more about the reasons behind their plans, rather than just discussing dollars and cents.
5. Do you have preferences for managing family wealth or assets?
If your family has significant or complex assets, consider the benefits of a neutral third-party trustee or corporate executor. "The more complex the estate, the more helpful it can be to have a third-party or corporate executor or trustee," Hughes notes. "It's about having someone with the expertise to manage assets appropriately and reduce the burden on family members, especially when emotions are already running high."
This approach can provide peace of mind for everyone involved and avoid potential family conflicts, particularly in blended families or those with strong dynamics.
Tip: Suggest this option by saying, "Some families use a corporate trustee to make things easier for everyone. Would you like to explore that idea?"
“One of the biggest things I hear people wish they'd talked to their parents about is family history and values.”- Megan Hughes, managing director of family office services with BOK Financial
Bonus question: Could you share how our family's wealth was created and any values that guided your financial decisions?
A question often overlooked but highly valued is asking about the origins of a family's wealth and the principles that shaped financial decisions over time. Hughes shared, "One of the biggest things I hear people wish they'd talked to their parents about is family history and values—understanding how the wealth, no matter the amount, was created and what financial decisions were important to them." This conversation can foster a deeper appreciation and commitment to family legacy.
Tip: Try framing this question with genuine curiosity: "I'd love to hear more about how you made certain financial decisions and what values guided you. It would help me understand and honor your legacy."
More financial conversation tips
1. Start small
Rather than tackling all of these questions in one sitting, begin with just one or two, especially if the topic feels delicate. Asking about document locations or trusted advisors can be a good starting point.
2. Keep it collaborative
Frame the conversation as a partnership in planning. Use language like, "I'm here to help support your plans however I can," which signals that your role is to assist, not control.
3. Be prepared for multiple conversations
This isn't a one-time conversation. Major life events—like retirement, changes in health or family milestones—are natural opportunities to revisit these discussions. "Each life change is a chance to realign plans, so they match current needs," said Hughes.
While not easy to ask, these questions can pave the way for a productive and respectful conversation that helps secure your parents' wishes, prevent potential misunderstandings and honor their legacy.
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