Holiday Reflections: Questions to Ask Your Family as You Celebrate the Season

Ellen Perry, Ali Hutchinson and Laura Salibello lay out five questions to ask during the holidays to spark discussion around the dinner table and provide tips for how to approach these conversations.

The holiday season brings families together, and these gatherings provide an opportunity to communicate and deepen relationships. At Brown Brothers Harriman (BBH), we advocate the importance of communication because in our experience working with families over generations, we have found it to be the key to what makes families thrive. Even the strongest and most resilient families face challenges when it comes to transitioning wealth, business and important roles like trustee from generation to generation. Studies have shown that where these transitions fail, the cause is not poor tax, legal or investment advice, but lack of communication and trust. While our clients understand the importance of communication, they often ask us for tips on how – how do we start the conversation? What do we say? Who should lead the conversation?

There are several questions that we have found inspire and engage family members of all generations. But before jumping into these, there are a few important considerations to keep in mind to ensure a productive conversation:

  • First, be open-minded, and do not pass judgement – now is not the time to “correct” your grandfather’s recollection of a story.
  • Next, be an active listener, and thank your family for engaging in a different way; trivia night might be “easier,” but this exercise will pay dividends for years to come.
  • Finally, be mindful of the moment, and don’t just dive right in – take time to ask how everyone is doing, and take note of the energy they are bringing that day. Use your intuition – it’s OK to skip a question or reschedule and just have a simple catch-up (or trivia night!) if that’s what your family needs in the moment.

Now that you know the ground rules, here are several questions to get started. We hope they spark conversation at your dinner table!

  • What does our family do right? How can we do more? Reminder: Focus on the positive.
  • What’s a hidden light or quality in each family member? Skip the obvious! It’s a gift to feel seen.
  • What’s your favorite family story? Why? Try to go beyond just recounting the story and explain why you can’t forget it.
  • Bring or describe your favorite childhood picture of you or of someone in the meeting – why do you love it?
  • One of the characteristics of families who thrive is the ability to forgive well. Do we forgive well? Can we be better? How?

BBH provides tools and resources to help families engage in conversations around wealth and values. Please reach out if we can help you navigate these discussions.


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