Building Bridges at the Holiday Table
Turn Your Conversations to Philanthropy this Holiday Season
Written by Melissa Baxter, WCCF President
In the next few months, many holidays will be celebrated by families across our community, and those gatherings will likely include a meal, togetherness, and maybe a football game or two. While the old adage is to avoid talk of politics and religion, we suggest the topic of philanthropy as a perfect springboard for meaningful conversations. Here are some ways to begin the conversation.

Set the Scene
Contextualize the topic: Start by mentioning the joy of coming together over shared meals and traditions. Set a warm tone to introduce philanthropy as a natural extension of the holiday spirit, focusing on generosity and gratitude.
Prompt with personal experiences: Frame questions using a conversational tone, inviting personal sharing and minimizing any financial pressure.
Encourage Storytelling with Prompts
Volunteer Stories
“What’s a volunteer experience you’ve enjoyed this year, or in past years?”
Sharing stories can inspire and reveal diverse community involvement that sparks ideas for others.
Imagining Impact
“If money was not a barrier, what difference would you love to make?”
This question fuels inspiration, and it can reveal unique passions that family and friends might share.
Charitable Focus
“What inspires you when you decide where to give, whether it’s time or resources?”
Understanding others’ motivations offers insights and might broaden perspectives on charitable causes.
Cultivate Legacy Conversations
Discuss family traditions and values: “Are there ways you’re hoping to continue or start a family tradition of giving?” This can open discussions on family donations, volunteer days, or shared causes as part of family legacy-building.
Plan together: For those interested, consider planning an annual family giving project or volunteer event. This can bond family members over shared causes and deepen community connections.
Passing the torch: Talk about any plans you may have to name family members as successor advisors for charitable funds or to entrust future giving through your estate planning.
Does your family value service, health, education, creativity?
Extend Resources and Learning Opportunities
Community connection: Offer information on local organizations, such as the Waukesha County Community Foundation, to help family members learn how to focus their philanthropy in ways that resonate with them.
Provide resources: Mention the National Center for Family Philanthropy as a place for more ideas on cross-generational giving discussions.
Bringing the topic of philanthropy to the table encourages open-hearted discussions that can strengthen family ties around shared values. Wishing you a wonderful holiday season and a time of fellowship with friends and family!