Summary
The holidays bring everyone together! It’s the perfect time for getting in real face time. Instead of reciting the latest headlines, advocate for the opportunity to address money topics like financial literacy for the kids in the family, the importance of a will, or how to financially overcome tough job markets
Many of the communities that would benefit most from financial conversations have them the least!
A short, caring check-in can change the temperature in the room and the future on paper.
How do you start a deep conversation over holiday dinner? Let’s break it down so it’s less intimidating.
Start a conversation with intention. Give your family a heads up before the gathering and ask for a dedicated slice of time. Keep the conversation simple and inclusive with a goal around protecting family wealth and helping each other to succeed financially.
Use some of these openers to get the conversation rolling:
- What family values should guide money decisions?
- If someone was out of work for three months, what would help look like?
- With job markets changing and young people greatly affected, what are some side hustles they can pursue now to build skills and income?
Make sure to stick to an agenda so you can address important topics of concern while leaving time to focus solely on fun topics over the dinner table.
Listen first to everyone’s financial concerns and encourage everyone to withhold judgment. Setting the tone as collaborative and constructive is important for the success of the conversation.
Try a 40-minute agenda that keeps the conversation focused:
- 10 min for values. What we are protecting, like job security, home, education, and legacy.
- 10 min for facts. Where documents live, who is listed on what, and key contacts.
- 10 min for what matters for each generation right now. For kids, simple financial literacy goals. For young adults, near-term support in a tough job market and steps to build stability. For elders, wishes for legacy, housing, and care.
- 10 min for risks and roles. Job loss, health events, caregiving, and who does what.
After the agenda, capture decisions in one place.
Appoint someone (the most organized in the family) to act as the chief financial officer. They will create a central folder or notes to follow, assign everyone their tasks, and schedule reminders for the year.
Before people head out, add a 60-day check-in to the calendar and send a short recap so everyone knows their tasks and important dates.
Lastly, share #OneTransaction resources so your family members can collectively work together on closing the wealth gap!
Money conversations are an act of care. Claim your 40-minute financial conversation and leave the table with clarity that protects the people you love the most!



