Reflective Conversation Starters for your End-of-Year Gatherings

The time of end-of-year parties and family gatherings is upon us at a time when conversations are trickier than ever to navigate with so much to divide us.?

One compelling option might be to keep things light and superficial.

Or how ‘bout we utilize these opportunities to invite meaningful personal reflections?

After all, these shorter days and the end of the calendar year lend themselves to looking back.?

In the spirit of connection and reflection, I’d like to set you a challenge to use the next few weeks to connect with those around you by initiating meaningful conversations.?

Here are 5 meaningful conversation starters and tips on how to facilitate them at a party where you mingle as well as at a sit-down dinner.?

And since any time we speak is an opportunity to practice our speaking skills and expand our speaking confidence, I’ll share ways for you to do that too.?

How to start meaningful conversations

So how do you introduce these deep conversation starters to initiate meaningful conversations?

1. Give advance thought to your topic(s)

First off, if you’re going to a party, choose 2 or 3 of your favorites to have up your sleeve to try out in different conversations.

For a sit-down meal in a restaurant or hosting at home, consider one or two questions that you would enjoy talking about and have them at the ready.?

I find that one deeper question is plenty for a meal where you may also want to catch up more casually with one another. But this all depends on the number of people attending, how well you know each other, and how frequently you see one another.?

Some people lean into personal sharing. Some find it awkward. You’ll have to put out your feelers to find the right balance.?

Use these tips to invite conversations

2. Introduce the question

If you’re mingling at a party, simply ask the question when there’s a lull in the conversation.

If you’re at a dinner party, you’ll be introducing the question as an activity.?

Say something like, “So I’ve been thinking this week about [topic] and, if you’re all up for it, I thought perhaps we could go around and all share our answers. I’d love to hear what it is for each of you. What do you think.”

Introducing the idea will invariably invite clarifying questions or suggestions. Don’t be rigid about the rules. Listen to the ideas that get brought up but quickly land on the process so that you can get to the good part– sharing your thoughts.

3. Make sure everyone gets a chance to share

I’m a stickler for sharing air time. At a gathering, it often happens that some people dominate the airtime. One reason that I like this game or structure is that it ensures everyone gets time in the limelight– especially those of us who don't get as many opportunities to s or avoid them.

At a table, you don’t need to go around in a particular order. People can share when they’re ready. Just ensure that everyone gets a chance to share their answer—including you!

When mingling at a party, usually if you ask others a question first, they’ll probably ask you for your answer once they’ve given theirs. But if they don’t, don’t be afraid to jump in before the conversation moves on with something like, “For me, I’d say it is___.”

If another person is standing in the group, invite them in– “What do YOU think? What’s it for you?”

4. Respond to others’ answers

In a large group, it makes sense for everyone to share their answers without commenting on other people’s. My family does this on Thanksgiving, so even if there are twenty of us, everyone gets a chance to say a line about what they are grateful for.?

In general, though, responding to each other makes for a much more engaging conversation and, ultimately, more connection. Certain kinds of responses, and positive reflections, create a feeling of safety to speak particularly for those who hang back.?

Model these responses and likely others will follow your lead.?

• “I love how you chose to __. I wouldn’t have thought of that.” “Such a great story. I loved how you built the suspense.”
• ”That’s cool how it ties back to this thing in your childhood.”?
• “That’s so brave (innovative, kind, etc). I’m going to have to remember to try that out.”
• “I love that phrase you used, ___”

For people whose responses are brief, ask follow-up questions.?

5. Adding more structure

If you think your group would be open to turning these meaningful conversation starters into more of a game, you could come up with some rules and guidelines.

For example, you specify that everyone has two minutes to share their thoughts (and someone sets their phone timer) or that when it’s your turn you say one thing you liked or appreciated about what the person before you said.

Use your conversations to expand your self-expression

Starting conversations like this is worth doing just to have fun and connect with other people.?

But you can also use these conversations to practice, expand, and improve your speaking confidence and skills.

You’re getting practice in speaking and leadership skills every time you:

• initiate and facilitate conversations.?
• Listen well, to find and articulate what you like and appreciate in what other people say or how they say it.?

You’re also getting practice in “thinking on your feet.”

Keep in mind:

1. This is an opportunity to practice taking up space. Challenge yourself not to rush through your answer. Let yourself take center stage, even just for a minute.
2. Be curious about what you might say. Maybe you’ll learn something new about yourself.
3. Don’t pressure yourself to be “perfect” in any way. Rather, use the opportunity to explore your thoughts, and experiment with how you express yourself. Make it a spiritual practice where you honor, accept, and appreciate whatever happens to come out of your mouth in the moment. Even if next time you would do it a different way.

5 meaningful Conversation Starters That look back over the Year

These are some questions that I’d like to talk about. Use them as inspiration or a jumping-off place to come up with your own.

1. Where have you traveled this past year and what did you like best about it?
2. What was challenging for you this year? How did you navigate it and/or what learning or benefit came from it?
3. What’s something you intended to do this past year but didn’t get around to doing?
4. What things do you feel proud of from this year– in your work or personal life?
5. What daily routines did you try out this year and which ones stuck and which didn’t?

What questions will you ask this season? I'd love to hear your ideas!

Here’s to having more meaningful conversations this holiday season!

A bit about me, Linda Ugelow

I help leaders, professionals, authors, and entrepreneurs transform the dread of speaking into loving it instead, whether it's in-person, online, in the media, or in the meeting room. Rather than tell you to “feel the fear and do it anyway”, I help you uncover and resolve the root causes of the anxiety so you can be free of the triggers from the past. I also believe that speaking is our human design. Let’s use the speaking we already do to mindfully and enjoyably expand our skills and mastery. To learn more about how to love your speaking, check out my podcast and book– Delight in the Limelight.?