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Money and family: How to navigate financial conversations

JR Williams, CFP® & Jack Howard · ·4 min read

Money conversations aren’t always easy, especially when it comes to talking to parents or other loved ones about the future.

Even for people who have a close relationship with their family, talking about money can be uncomfortable or even taboo. But avoiding these conversations can ultimately lead to stress, conflict or regret.

However, when managed correctly, these conversations can create transparency that ultimately fosters an even stronger bond. To help find the right approach for discussing finances with your loved ones, we spoke with Ally Head of Money Wellness Jack Howard and Ally Invest Senior Director JR Williams for tips, conversation starters and more.

Read more: What does a financial advisor do? Your common questions, answered

Why these conversations are usually about more than money

For many people, talking with their children — even once they’re adults — or other family members about personal finances can come with strong emotions, such as:

  • Shame around financial readiness: It’s possible some feel they haven’t prepared for their golden years as thoroughly as they should have.

  • Avoidance and denial: Acknowledging mortality can be difficult, making these conversations something your loved ones don’t want to deal with.

  • Fear of losing independence or control: Aging is hard for many as they feel they’re no longer in control over their own lives.

  • Changing family roles and identity shifts: It can be tough when parents feel their children or other family members — who they may have always cared for up to this point — are now the ones in charge.

How to prepare for a productive conversation

Taking the following steps can be the difference between a constructive discussion and a shutdown.

Create intentional time and space

Setting aside time to have this conversation can ensure that your loved ones don’t feel blindsided. Giving them a heads up also allows everyone to come prepared.

Clarify your purpose

Coming into the conversation with a clear purpose, such as wanting to ensure your parents’ money goes where they want it to after death, can lead to them being more open.

Set realistic expectations

Discussing a lifetime of financial decisions likely won’t happen in one sitting. Make sure your family member knows this will probably be an ongoing conversation rather than a one-time event.

How to start the conversation

One of the hardest parts of this type of conversation is knowing where to start. Our experts recommend taking a values-based approach. Consider using phrases like:

  • “As we think about your future, what’s most important to you in how your money is used? For example, donations to a specific cause or toward your grandchildren’s education?

  • “What are you most proud of with what you’ve done with your money so far?”

  • “In an ideal world, how would you like to use your money now?”

Having a deeper understanding of your loved one’s values and the intent they have for their money can help them feel more in control of their financial future and the legacy they’re leaving behind.

Learn more: Explore additional conversation starters in our Money Roots: Money + Love workshop

When to start the conversation

The best time to talk about finances is before you have to. But life sometimes doesn’t allow for that.

Other common scenarios that could revolve around lifestyle shifts include:

  • Turning 50 or entering retirement planning stages

  • New medical diagnoses or health changes

  • Decisions around downsizing or relocation

One of the hardest parts of this type of conversation is knowing where to start. Our experts recommend taking a values-based approach.

Key financial topics to cover

Leverage these topics as a practical starting point for conversations with family:

  • Income and cash flow: How much money do they have coming in each month and how much are they spending?

  • Health and long-term care: What are their healthcare preferences and long-term care expectations?

  • Estate planning: Are their wills, trusts and power of attorney in order?

  • Organizing financial and legal information: Where are important documents stored?

What to do if the conversation goes sideways

It’s possible that any of these topics could lead to emotional or heated discussions, causing you or your loved ones to shut down the conversation. If emotions escalate:

  • Pause, slow down and reflect back on what you heard

  • Don’t give up — their resistance may stem more from fear or shame rather than the topic of money itself

  • Suggest working with a third-party, such as an estate planning or specialized law attorney, financial advisor, tax professional or family support therapist

Next steps after the first discussion

Once you’ve opened the door on the topic, keep the conversation going:

  • Schedule a follow-up discussion

  • Create a basic inventory of documents and accounts

  • Identify trusted contacts and professional support

  • Plan regular check-ins and reviews

  • Reframe planning as an act of care, not control

Turning difficult discussions into stronger trust

While having financial conversations with family isn’t always easy, it can be very meaningful. These discussions help ensure that the people you love feel supported and secure, and that their values are honored now and in the years ahead.

Written by
JR Williams, Senior Director, Ally Invest
JR Williams, CFP®
Senior Director, Ally Invest
Headshot of Jack Howard, head of money wellness at Ally Financial
Jack Howard
Head of Money Wellness, Ally Financial

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