Every year around Christmas, stores and malls across America are transformed into winter wonderlands, complete with elves, ornaments, artificial snow, and larger-than-life decorations.
Many children stare in wide-eyed wonder as they wait to sit on Santa’s lap and answer a singularly important question: What do you want for Christmas this year?
While some children are prepared to share their most heartfelt wishes, others may need a little prompting. Santa may start with gentler questions to build rapport and earn their trust: How old are you? Have you been good this year? Do you have brothers or sisters?
As adults, we might find the mall Santa a bit campy, but there is a real lesson here for advisors: relaxed, friendly small talk and the right questions can open the door to deeper conversations about family, goals, and values.
A cozy holiday chat with your clients is the professional version of a fireside moment that can help clients feel at ease, open up about what matters most, and start conversations that naturally lead to deeper planning discussions.
Focused around popular holiday themes, here are a few prompts—talking points that blend festive facts with estate planning insights and open-ended questions—for sparking conversations that can help clients share what matters most to them.
Season of Giving
Estate Planning Fact: Approximately 68 percent of Americans do not have a will,1 yet everyone has a legacy to pass on, regardless of their net worth.
Holiday Fact: On average, each American plans to spend $890.49 on holiday gifts, food, decorations, and other holiday items this year.2
Conversation Starter: “If you could leave one meaningful gift to your loved ones, what would it be?”
Treasures of Time
Estate Planning Fact: Wills can include family heirlooms such as holiday china, vintage ornaments, menorahs, or kinara.
Holiday Fact: More than 97 percent of Americans decorate the inside of their home for the holidays.3 Many families have heirloom ornaments that preserve family history through décor.
Conversation Starter: “Which family traditions or heirlooms mean the most to you?”
Peace on Earth
Estate Planning Fact: An estate plan can help avoid family conflict by providing loved ones with clear instructions and eliminating guesswork during emotionally challenging times.
Holiday Fact: Nearly 40 percent of families report disagreements during holiday gatherings. About one-third of those arguments turn into lasting family problems, and almost 20 percent of people say the fights even caused someone to change their will or estate plan.4
Conversation Starter: “Has your family faced past disagreements that might shape how you plan for the future?”
Shorter Days
Estate Planning Fact: A trust can help shorten or avoid the lengthy probate process when time is of the essence.
Holiday Fact: The winter solstice (December 21, 2025) marks the shortest day of the year but not the earliest sunset, which occurs about two weeks earlier.5
Conversation Starter: “What matters most to you—time saved, privacy, or control—when it comes to settling your affairs?”
Fur-Ever Gifts
Estate Planning Fact: Estate plans can include provisions for pets; celebrity designer Karl Lagerfeld famously left millions to his cat.
Holiday Fact: A 2024 survey found that 6 percent of Americans planned to spend over $1,000 on holiday gifts for their pets, with the largest segment of pet owners (15 percent) planning to spend between $51 and $75.6
Conversation Starter: “If something unexpected happened, who would step in to look after your pets, and how would you want them cared for?”
Will Power Season
Estate Planning Fact: If your client dies without a will, default state laws could determine who inherits from them and how much their heirs get.
Holiday Fact: Unlike UPS and FedEx—private businesses that can set their own company policies—the United States Postal Service is a government agency regulated by Congress. By law, it must deliver to every US address, even the most remote ones.7
Conversation Starter: “How comfortable are you with letting state law decide who inherits your assets?”
Little Lights, Bright Futures
Estate Planning Fact: Many parents with minor children have no will in place.8
Holiday Fact: Parents spend an average of around $173 per child on holiday gifts. 9
Conversation Starter: “Whom would you trust to care for your children if you cannot, and what qualities matter most in that role?
Wills for All Seasons
Estate Planning Fact: Adults under 35 are now more likely to have an estate plan than those aged 35–54,10 reversing a long-held assumption.
Holiday Fact: Millennials and Gen Z spend more on self-gifting than any other age group,11 redefining what “giving” means.
Conversation Starter: “How do you see your stage of life shaping the kind of legacy you want to build?”
Making a List
Estate Planning Fact: Forty-three percent of Americans without a will cite procrastination as the main reason.12
Holiday Fact: A Gallup poll from 2023 found that nearly half of shoppers (49 percent) planned to do most of their holiday shopping in December, while 16 percent planned to do all of their holiday shopping in December.13
Conversation Starter: “What is one estate planning task you have been meaning to check off your list?”
Tidings of Charity
Estate Planning Fact: A person can set aside funds in their estate plan to give to a charitable cause in a family member’s name.
Holiday Fact: About 30 percent of annual charitable donations occur in December, driven by a combination of holiday generosity and tax incentives.14
Conversation Starter: “Are there causes or organizations that have made a lasting impact on your life?”
Good Communication = Good Tidings (and Even Better Planning)
A well-timed question and a little warmth can turn a seasonal chat into the start of a stronger, more-lasting relationship. Just like Santa gently prompts children to share their wishes, thoughtful questions and a welcoming atmosphere help clients share their hopes, priorities, and plans for the future. If you or your clients have estate planning questions, let us know.
- Rachel Lustbader, 2024 Wills and Estate Planning Study, Caring (Sept. 16, 2025), https://www.caring.com/resources/2024-wills-survey. ↩︎
- Consumers to Spend Second-Highest Amount on Record, According to NRF Holiday Survey, Nat’l Retail Found. (Oct. 16, 2025), https://nrf.com/media-center/press-releases/consumers-to-spend-second-highest-amount-on-record-according-to-nrf-holiday-survey. ↩︎
- Julia Pelly, Christmas Decor Trends 2025: What Are the Most Popular Decorations in America?, Angi (Oct. 9, 2025), https://www.angi.com/articles/christmas-decor-trends.htm. ↩︎
- Family Arguments During the Holidays can have Profound Consequences, According to New Survey from Trust and Will, Trust & Will (Nov. 19, 2024), https://trustandwill.com/learn/family-arguments-holidays-consequences. ↩︎
- Jane Rose & Karin Crompton, 25 Facts About the Winter Solstice, the Shortest Day of the Year, Mental Floss (Dec. 18, 2023), https://www.mentalfloss.com/article/72659/10-things-you-probably-didnt-know-about-winter-solstice. ↩︎
- Betty Lin-Fisher, Pet ownership is up. So is consumer spending on dogs, cats for the holidays, USA Today (Dec. 21, 2024), https://www.usatoday.com/story/money/2024/12/21/pet-spending-holiday-statistics/76947872007. ↩︎
- Tyler Powell and David Wessel, How is the U.S. Postal Service governed and funded?, Brookings (Aug. 26, 2020), https://www.brookings.edu/articles/how-is-the-u-s-postal-service-governed-and-funded. ↩︎
- Victoria Lurie, 2025 Wills and Estate Planning Study, Caring (Sept. 17, 2025), https://www.caring.com/resources/wills-survey. ↩︎
- Stephanie Weaver, Here’s how much parents spend on holiday gifts for each child, Live Now Fox (Nov. 21, 2024), https://www.livenowfox.com/news/how-much-parents-spend-holiday-gifts-each-child. ↩︎
- Victoria Lurie, 2025 Wills and Estate Planning Study, Caring (Sept. 17, 2025), https://www.caring.com/resources/wills-survey. ↩︎
- Jing Feng, Young adults are keeping themselves on their holiday gift lists, NBC News (Dec. 22, 2024), https://www.nbcnews.com/business/consumer/young-adults-are-keeping-holiday-gift-lists-rcna184447. ↩︎
- Victoria Lurie, 2025 Wills and Estate Planning Study, Caring (Sept. 17, 2025), https://www.caring.com/resources/2024-wills-survey. ↩︎
- Jeffrey M. Jones, December Holiday Rush for Half of U.S. Shoppers, Gallup (Dec. 7, 2023), https://news.gallup.com/poll/545537/december-holiday-rush-half-shoppers.aspx. ↩︎
- Daniel Hall, Why 30% Donate in December: Year-End Giving Statistics, Harness, https://www.goharness.com/blog-posts/year-end-giving-statistics. ↩︎