We in the US are all heading into the vaunted holiday season. I love this time of year. Email slows down, travel is usually all pleasure, rom-coms are viewed, fireplaces are lit. Sure, that’s not the holidays for everyone, but it’s what I imagine mine will look like. And maybe yours.
There’s another thing I love about holidays: talking and connecting with people I cherish without the pressure of ending a conversation two minutes before the hour (pee break, fill water bottle, back on Zoom). But I do at times find myself at holiday gatherings having what I regard as the world’s least interesting conversations. This is subjective, I know. But still. I want to share my yummiest questions for engaging holiday conversations in case you feel like being a catalyst this year.
The three central thrusts behind these questions are, first, that I love learning. I want to learn. I want to talk to people who love learning about what they have been learning. If you tell me you are in love with a podcast because it’s teaching you all about a discrete period of history that feels relevant today, I will go listen to that pod. I will report back to you. Second, great conversations start with generous questions. Generous questions reflect genuine care and attention. They are open and not closed. They invite depth. Third, interesting conversations depend not just on generous initial questions, but also on great listening and a well-tuned, non-generic follow-up question that reflects the quality of your listening and your level of interest. Great questions not only promote great conversations, they promote meaningful connection. And I, for one, want more of that this holiday season.
My favorite questions to ask at holiday gatherings (and one bonus generic follow up in case you’re at a loss):
- What have you been learning lately, about yourself or someone else or some interest you have? If I wanted to learn that myself, how would you recommend I do it?
- What is one thing that has delighted you lately or over the last year? What about it was so special?
- What do the year-end holidays mean to you? Do you have memories, positive or negative, that affect how you feel about this time of year?
- Is there someone you wish were here tonight who isn’t? What would be different about this gathering if that person were here?
- When you are in “holiday mode” (if you have a holiday mode), what behaviors or personas do you bring to the table that don’t feel like the “real you?” What purpose do those personas serve during this time of year?
- Did you set any goals or have any resolutions or intentions for 2024? How have you been doing on those?
- Who has felt like your closest friend lately? How do you two engage in friendship (in-person, phone calls, walks)? What special sauce does this friend bring to your life?
- If I really knew you and how your life is going, what is one thing I would know?
- What feels new about you that has been emerging this year?
- What do you imagine would bring you 10% more happiness other than more time or money? What’s the real reason you don’t have that?
- What “work” are you doing that is most meaningful to you, whether that is a paid job or something else?
Some of these may sound more edgy than others, depending on your holiday gathering audience, but I hope you’ll try one or two out this year
To complete the picture, I’d like to share my least favorite questions:
- When did you get to town? How long are you staying?
- What do you guys have planned for tomorrow?
- How was your trip to ______?
- What are your kids up to (asked before any question is asked about the person who may happen to be a parent)?
- Do you have any interest in this football game (gesturing toward TV)?
- How’s the turkey?
- How’s your home renovation?
- What is your brother/sister/mother/father/anyone else not in attendance doing for the holiday?
If you have a classic one to embrace or avoid, let me know over on LinkedIn or reply to this email if you’re on my newsletter list. If you’re not, sign up on my site.
If you’re looking for more great questions and the argument for asking them, check out my new book Leader Coach: Scaling Conscious Leadership at Work, which works great at home or on the job. The perfect holiday gift for any kind of leader in your life.
