If you’re already feeling uneasy about attending upcoming holiday receptions, mixers, networking events and year-end conferences, you’re not alone. Even the most seasoned executives often find the casual conversations and “small talk” exhausting.
As a business executive and an extrovert, people often think “small talk” comes easily to me. But there were times when I struggled to walk into a crowded room or felt lost if someone brought up a topic I didn’t know much about. Receptions, conferences, and dinner events sometimes left me drained. A mentor once told me to focus on being genuinely curious and to have a few conversation starters ready. This advice made connecting with others in these settings much easier and less tiring.
In this issue of InFocus, I’m sharing my Top 10 strategies and conversation starters to help you make genuine connections. Bring these ideas with you to events, and you’ll find it easier to start real conversations while maintaining your energy. Be yourself, adapt the examples to fit your style and situation, ask open-ended questions, and be sure to “read the room.”
Top 10 Conversation Starters
1. Lead with genuine curiosity.
Instead of “What do you do?”
Try: “What’s keeping you busiest right now?” or “What are you most excited about heading into next year?”
This approach invites people to share what matters most to them.
2. Ask about the journey, not just the destination.
Try: “How did you get into this field?” or “What led you to your current role?”
Most people enjoy sharing their stories, which helps you get to know them better.
3. Make it about the moment.
Use the shared experience: “This is my first time at this event—have you been before?” or “I’m impressed by the turnout. What brought you here tonight?”
Simply being at the same event already gives you common ground.
4. Connect to the event theme or content.
Try: “What brought you to this event? Are you exploring anything specific?” or “Have you attended any sessions today that stood out to you?”
These questions help you find shared interests and keep the conversation going.
5. Offer a specific observation or compliment.
Instead of generic praise, try: “I saw your post about [specific topic]—I’d love to hear more about that,” or “I heard you speak on the panel earlier. Your point about [specific thing] really resonated.”
When you’re specific, it shows you were really listening.
6. Ask for their perspective, not their opinion.
Instead of “What do you think about [industry trend]?”
Try: “How are you seeing [industry trend] play out in your organization?”
This keeps the conversation focused on real experiences instead of just opinions.
7. Tap into travel plans.
Try: “Do you have any travel coming up—holiday plans or work trips?” or “Are you staying local for the holidays or heading somewhere?”
Most people can relate to travel, and it often leads to real conversations.
8. Ask about accomplishments.
Try: “What are you most proud of accomplishing this year?” or “What’s been a highlight for you professionally/personally this year?”
Year-end questions help people reflect and share what’s important to them.
9. Ask for their recommendations.
Try: “I’m always looking for good recommendations—any books, podcasts, restaurants, destinations [fill in the blank] that have been valuable to you lately?” or “What’s something you’ve learned recently/something you’ve done that’s changed how you think about your work?”
This shows you value their ideas and gives you a chance to reconnect later.
10. Create an easy exit and re-entry.
You can say, “I want to meet a few more people tonight, but I’d like to keep this conversation going. Can I get your contact info?”
After the event, send a thank-you message that mentions the topics you discussed. This makes it easy to follow up, shows you respect their time, and creates an opportunity to connect again.
What matters most is being yourself, paying attention to what’s going on around you, and initiating meaningful conversations and connections. Adapt these tips to fit your style and the situation. You don’t have to impress anyone or try to stand out. Just focus on being present and making connections. When you shift to genuinely connecting, events become less tiring.
Plan short breaks or set time limits to keep your energy up and stay engaged. Take a quick pause, step outside for some fresh air, or find a quiet spot to recharge. These small breaks help you stay present and avoid burnout.
Pick two or three conversation starters that feel right for you. Use them at your next event and see how connections happen. Afterward, think about which ones felt most natural and worked best to help guide your approach for the next event.
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About the Author
Carolyn Hillegass is CEO and Founder of The Outcomes Coach, and an ICF-certified executive coach with 30+ years’ C-suite experience in healthcare, tech, and emerging business sectors. She provides coaching tailored to the unique needs of individuals, teams, and organizations within the healthcare sector, including health services, life sciences, pharmaceuticals, biotechnology, medical technology, and digital health.
