It's even worse if you don't know what to say to break the ice.
After 20 years as an author and journalist, I've learned a bit about asking people good introductory questions, and keeping them talking. So if your 2020 resolution is to get better at this, I hope you'll find the suggestions in this article useful.
Below, I'll share my best general tips, plus 10 sample questions that you can use to start conversations. They'll keep the discussion going, and leave people feeling positive about you, and remembering you.
First, the overall tips. All effective ice-breaker questions have three key things in common:
- They're open-ended. The one thing you don't want to do is to ask a yes or no question, or one that can be answered in just a few words. Your goal is to spark conversation.
- They're specific. This might seem like it's the opposite of open-ended, but it's not. You want to focus the conversation, hopefully on a topic that will be interesting and even fun, but won't lead to you putting your foot in your mouth.
- They're multifaceted. Ideally, you want to ask a question that will suggest the answer to several other questions. So, if you ask someone what they did over the weekend, you're also perhaps asking them about their family, their friends, and their values.
Listen to the answers!
I can't emphasize this enough: There's one more basic, crucial tip before we get into the sample questions.
When you ask an icebreaker question, you must listen actively to the answer!
So many people forget this. They ask the question, the other person starts talking, instantly they switch off -- looking around for someone else to talk to, or deciding the answer wasn't interesting enough.
Please, remember that your job isn't done with one question.
Instead, you have to listen and come up with two to three follow-up questions.
That's how a real conversation works.
With that, here are 10 samples that you can use to get started:
1. If our industry didn't exist, what do you think you'd do for a living?
I like this one to start because it's professional, but it's not predictable or boring. Depending on the answer, you can immediately shift back to talking about the industry you share, if that seems more appropriate. Or you can ask follow ups that can tell you a lot about the person you've just met.
2. Have you ever had a bad job? (Follow up: Did you learn anything useful from it?)
I asked the subscribers to my daily email newsletter this question, and the replies were amazing. Lots of talk about working in restaurants. (My bad job story was about working in a call center.) Almost everyone has a story like this, and most people like to share the bright side, if they can identify it.
3. What was your first apartment like?
This is a great question, because it can prompt nostalgia, and it's probably about a time before they achieved their current success. People like talking about it. Also, if you happen to ask someone who is still living their first apartment, it opens up a whole other line of inquiry.
4. Have you had your 15 minutes of fame?
Claire Lew at Know Your Team gets credit for this one. It can be defined in so many ways, and sometimes you'll learn fascinating things about people. So far my 15 minutes had to do with quitting a job after one day, writing about it, being interviewed on national television, and winding up with my picture on The Tonight Show With Jimmy Fallon. But I'm hoping for something better down the road.
5. What's your favorite children's book?
I love this one, because you're actually asking several questions. One is whether the other person has kids. If they do, and you do, boom: instant rapport. But even if they don't, they can reach into their childhood, or to their experiences with nieces or nephews or other kids, and come up with an answer.
6. You've just learned they're making a movie about your life, and you control the casting. Who should play you?
Again, you're asking more than one question -- both who should play them (often based on appearance), but also: why would they make a movie about you? What would it be about? The follow-ups almost write themselves.
7. What fashion trend should we bring back?
As an alternative: "What word should we all start using again?" But I find people sometimes get stumped when you ask them about words. Everyone can talk about clothes.
8. What's the biggest change you've experienced in the last 10 years?
This one will be especially good for a few more weeks, as we launch a new decade, or if you're ice-breaking at a New Year's Eve party. I used it on my email newsletter, and you learn interesting things. In real life, I asked an acquaintance lately, who replied: "That's easy. Getting out of jail." I'd had no idea.
9. What's the best thing you've read recently?
I like to ask it this way because not everyone reads many books, and some people feel self-conscious about that. So the best "thing" they've read could refer to an article or a blog post (or a column on Inc.com). You're really asking them what they think is interesting. Most people like to talk about that.
10. What were you doing exactly one week ago?
You might provide the person with good fodder for a story, or you might prompt them to pivot quickly. For example, my literal answer to this question right now would be: "Packing to go away for Christmas." But that could easily lead to a description of where we went, and what we did, and that would be far more interesting.