When Difficult Conversations Come up at Thanksgiving

Thanksgiving can bring a sense of gratitude, happiness… and stress: Judgmental aunts. Nosy cousins. Prying grandmas. Boastful cousins. Jealous brothers. Successful sisters. Uncomfortable in-laws.

When you bring your extended family all around the same dinner table, things can get heated. Difficult topics can come up: money, politics, religion, relationships, career choices, academic success, your appearance, your favorite sports team, the turkey being slightly undercooked… Things can blow up to a screaming match that brings you to packing up your things and doing the five-hour drive home that very night.

Talking about any of these topics — especially money — can be challenging during the holidays, especially when you hear your relative’s voice laden with judgment as heavy as the gravy on the dinner table: “You spend how much on Christmas presents? You’re taking out a business loan? You’re sending your kid to that expensive art school?”

When you don’t see eye to eye with family members, it can be hard to stay even keeled during the holidays. But this can be the perfect opportunity to bring up difficult money topics. It may seem counterintuitive, considering how tense things can get around the Thanksgiving dinner table, but it’s best to have difficult conversations in person and when everyone involved is there.

For instance, maybe you and your siblings need to talk about long-term care options for your parents, and how much they will cost. As tough as these conversations can be, you need to have them eventually, and the holidays can be a good time to have them.

4 Tips on Effective Money Conversations

Talking about difficult topics takes courage — and preparation. Here are four tips for effective money conversations this Thanksgiving.

1. Be proactive.

By being proactive, and planning a conversation when you have time to talk things through calmly, you are a significant step ahead.

2. Don’t blindside the other person. Set a time, a topic and the length of time.

Pick a time when you both will be more relaxed and comfortable. Agree on how long you will talk. Some people are exhausted by long conversations, while others need to walk while talking about stressful topics.

3. Plainly tell them your intention regarding the conversation.

You don’t want to catch the other person off guard, but you also don’t want them to be on guard, arming themselves for battle. Tell them your intention and why the conversation is important to you.

4. Start small, prepare and practice.

Start with easier topics and work up to the bigger issues. Write down what you want to say and practice with yourself or with a friend.

Conversation Openers

If you’re wondering, “Okay, great, but how do I even begin the conversation?” try one of these conversation openers that Judy Ringer, conflict and communications skills trainer, recommends:

“I have something I’d like to discuss with you that I think will help us work together more effectively.”

“I’d like to talk about _____ with you, but first I’d like to get your point of view.”

“I need your help with what just happened. Do you have a few minutes to talk?”

“I need your help with something. Can we talk about it (soon)?” If the person says, “Sure, let me get back to you,” follow up with them.

“I think we have different perceptions about _____. I’d like to hear your thinking on this.”

“I’d like to talk about _____. I think we may have different ideas about how to _____.”

“I’d like to see if we might reach a better understanding about _____. I really want to hear your feelings about this and share my perspectives as well.”

Taking the Next Step

After having the first conversation, here are some tips on how to continue navigating money conversations with loved ones.

Commit to having family financial conversations now.

Talking now can help bring families together. Communication between family members can support your family’s financial goals.

Ask detailed questions and make sure loved ones know where important financial information can be found.

Don’t be afraid to ask even the most seemingly obvious questions. Family members should also learn the location of — and know how to access — important documents, along with keys to safety deposit boxes or other storage facilities.

Ensure your goals and values are understood.

A family meeting can ensure that your family not only understands your wishes, but also knows precisely how they should be honored.

Continue the conversation with regular, ongoing dialogue.

Family financial conversations are not one-time events. You should revisit your financial situation with your family regularly.

Get help from a professional.

A financial advisor can help arrange and provide assistance for a family meeting to help ensure peace of mind for you and your loved ones.

Attend One of Our Conversation Circles

At The Humphreys Group, we’ve discussed having difficult money conversations at our Conversation Circles in San Francisco. Our circles consist of a group of 12-15 women sitting together and talking about money and everything that goes with it — from our successes and fears to stories, behaviors and legacies we’ve adopted over the years.

Talking about money remains taboo, and the Circle provides safety and intention that supports a thoughtful discussion in which we can share and gain insights from other women.

As we reflect this Thanksgiving, we’re so grateful for the network of women who’ve attended our Conversation Circles over the years. We continue to be inspired by the impact that a group of women, talking together, can create. If you’re interested in attending one of our Conversation Circles, contact us today. And from all of us at The Humphreys Group, we wish you a happy Thanksgiving.

Diane Bourdo, CFP®
Diane Bourdo, CFP®

Diane Bourdo is the President of The Humphreys Group. Diane has dedicated her life’s work to helping women make smart financial decisions. For nearly 30 years, she has developed investment management and financial planning strategies that allow her clients to create lives that reflect their values. Diane was named an InvestmentNews 2020 Women to Watch and has been recognized in Forbes, SF Chronicle, NY Times and more for her work and writing.

Diane Bourdo, CFP®
Diane Bourdo, CFP®

Diane Bourdo is the President of The Humphreys Group. Diane has dedicated her life’s work to helping women make smart financial decisions. For nearly 30 years, she has developed investment management and financial planning strategies that allow her clients to create lives that reflect their values. Diane was named an InvestmentNews 2020 Women to Watch and has been recognized in Forbes, SF Chronicle, NY Times and more for her work and writing.

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