10 questions that will facilitate meaningful conversations at events


When it comes to event planning, organizers have no problem coming up with a stellar roster of speakers and arranging a good program. What they really struggle with is finding the right community building activities to get audience members to interact with each other in deep and meaningful ways.

We’re not talking about small talks here. Small talks are transactional and awkward and rarely ever results in lasting connections after the event. We’re talking about real conversations—dialogue that inspires excitement, empathy, and trust. And this is certainly a challenge as the meaningful conversation is usually reserved for more intimate connections, like long-time friends and family. But it is entirely possible. All they need to do is ask the right questions. 

The problem is not everyone has the social energy and know-how to get up close and personal with strangers at an event. This is where you come in.

As the event organizer, you need to play an active role in facilitating these conversations and supplying them with the right questions. 

The power of a good question

Questions are powerful tools in creating meaningful connections. Too often, people get stuck at “So what do you do?” or “What brings you here?” and can’t take off from there. That’s because these are stale, dead-end questions that are meant to break the awkward silence—not to get to know each other on a deeper level. 

If you leave your attendees to their own devices, these are likely the questions you’re going to hear them ask each other. To steer them in the right direction, get your audience to ask questions like these instead: 

1. What do you do outside of work? 

Asking a person about their job is pretty standard. But to be honest, not everyone is enthusiastic about their nine-to-five. This flips that question around and asks them what they do outside their job. This is the stuff they get into in their free time—a craft they’ve mastered or a sport they follow religiously. A question like this will surely put a glint in their eye.   

2. What was the worst job you’ve ever had? 

Nothing can get a person more riled up than the worst job they’ve ever had. Maybe it was when they interned at a fax company and they had to deliver everyone’s coffee at six in the morning, or the time they moonlighted as a telemarketer and got the phone put down on them nine times before lunch break. Not only will a question like this inspire some sort of emotion from attendees (disgust, amusement, gratitude), it also encourages empathy from others (“Oh, that must have been so hard!). 

3. If I knew you better, what’s something I would know about you? 

Sometimes the easiest way to get to know a person is to outright ask them about themselves. But instead of just saying “tell me about yourself,” which is vague and human resources-like, attendees can get more specific and ask them a question like this. After all, the goal is to become more than just strangers and acquaintances. Telling someone a personal detail about themselves is bound to break down preconceptions. 


4. Have you read any good books/watched any good movies lately? 

People can learn a lot about another person based on the books and movies that make it to the tops of their lists. Favourite Marvel character? Spider-man. Most-read author? Murakami. These questions lead to other questions and shed light on similar interests and, more excitingly, polar differences in opinion. Imagine someone saying something like “Actually, I didn’t like Bong Joon-ho’s critically acclaimed comedy-thriller Parasite that much.” If that doesn’t spark a conversation, what will? 

5. What are you most afraid of? 

A person’s fear is not something that comes up in the first conversation. But again, it’s something that incites a lot of emotion. They could be afraid of heights or spiders because of some bad childhood encounter. Or they could be afraid of more intangible things, like “failure” or “success.” These sorts of topics can help attendees dig deep into another’s persona. 

6. What’s the luckiest thing that’s happened to you? 

This question is interesting because something “lucky that’s happened to you” is a very specific way of putting things. After all, luck is arbitrary. Why would anyone ask that? But it’s interesting to see what people consider lucky. “I got really lucky with my wife! I don’t know how I convinced her to marry me”—these types of answers give insights on what the other is grateful for, and that’s a pretty solid topic for a conversation. 

7. What’s the most annoying question people often ask you? 

It’s surprising to hear the different questions people get bombarded with on a daily basis. Some of which are seemingly harmless, but bordering on rude like “where’s your accent from” or “how do you get your hair to curl that way?” Learning more about the types of questions people get asked on a regular basis also cultivates empathy and self-awareness—essential social lubricants for better relationships. (Let’s just hope no one’s asked it already!)

8. What do you say more often in life: yes or no? 

Is the other person a certified go-getter or a devout nay-sayer? Each attitude has its own philosophy and there’s definitely no wrong or right. But learning about the other’s reasonings can be an eye-opening experience for both parties. Does one tend to get pushed around and say “yes” to one’s every whim? Or does the other hold back in life by closing the door on every scary opportunity? 


9. What takes up too much of your time?

Learning about a person’s dislikes is just as important as learning about their likes. Something that “takes up too much of your time” is bound to be something that a person dislikes doing. Maybe long commutes take up too much of their time, or doing the dishes is really eating into their evenings. Sharing dislikes also opens up opportunities to share solutions, like listening to podcasts while on the commute or buying a dishwasher. Attendees will never know what fruitful advice may come out of these conversations!

10. When people ask you for help, what do they usually come to you for? 

Everyone’s good at something, right? And this question will help attendees figure out just what that is. Maybe this guy is the designated tech-dude who can troubleshoot any and all coding woes. Or maybe this girl is the go-to for any career-related advice. Whatever it is, the topic will likely be a point of pride for this person and help keep the conversation flowing. 

Getting them to ask the right questions

Now that you’ve got these questions on hand, how do you get your attendees to ask each other these questions? A typical unstructured networking event isn’t enough to break down social barriers and inspire one-on-one conversations. As the organizer, you need to put them in the proper environment and situation to get to know each other better. 

One way is to organize structured interactive activities, like a speed networking session or a targeted roundtable. But we find that these require a lot of props and planning beforehand. And it’s not always effective at getting people to converse with each other after the event. 

We recommend using a real-time audience interaction platform like Toasty. Audience members can connect to Toasty with just their phones by scanning a QR code. Once they’re in the event room, they can answer fun, customizable icebreaker questions, and get paired up with other like-minded participants. From there, they can use the app to ask each other some conversation-sparking questions and have a good time. 

We’ve found that live-technology is really effective at engaging personal connections. And everyone benefits from having real conversations—including you. 

Getting the audience to engage with each other in a meaningful way gives them the experience that they crave for when going to events. After all, the events industry is centred around in-person communication and human interaction. You can judge the success of an event by how much people are talking about it after the event has passed. 

Hopefully, these questions and community building activities at your event lead to more lasting and mutually beneficial connections in the long run. 

Need help coming up with more questions for your event? We’ve got some ready-to-use templates in Toasty Conversation Cards!