Laura Berlinsky-Schine

Small talk is hard. While some people find it natural to make conversation with colleagues, others struggle to come up with something—anything—to say. The trick is that there’s actually no trick. Practice and exposure to different situations will make conversation come more easily, but some people will always be nervous meeting and interacting with new people.

Fortunately, you can learn how to start a conversation in business situations and pique the interest of others. As you have exposure to different types of situations, chance are you’ll start to feel more comfortable interacting with colleagues, your boss, and others in your industry. Here are 31 interesting conversation starters to kick off small talk in a work context.

How to start a networking conversation

Networking events can be painful, especially if you’re an introvert who finds being around tons of people, including many you don’t know. Unfortunately, if you’re a professional, you’ll have to attend many throughout your career. Here are conversation starters you can use to make sure your next event goes smoothly.

1. “What brings you to this event?”

People love to talk about themselves in almost any situation. Asking them why they’re here gives them license to talk about their favorite subject: themselves. After you ask them why they came to the event, they’ll probably ask you the same question, and then you get to talk about you. This starter can help you segue into a broader conversation about your roles in the industry and goals for the event.

2. “How often do you come to these events?”

Another variation is “Have you been to one of these events before?”, but open-ended questions that don’t allow a fellow attendee to give a yes-or-no response will encourage her to keep talking. If she’s been to this event before, you can follow up by asking for tips and finding out what to expect. If she hasn’t, you’ve established common ground and can commiserate over being “newbies” together. Then, you can discuss your expectations and ask for hers, as well as make small talk about your careers in general.

3. “What’s your role?”

Again, asking someone what she does in the industry allows her to talk more about herself. Asking this question can also benefit you in other ways. For instance, perhaps you have similar positions and can share your perspectives on it. Maybe you aspire to her role and could ask for advice on how to climb the ladder. It’s also possible she has a role about which you have questions or don’t know a great deal, and you can learn more about the different functions within the workplace.

4. “I’m a huge admirer.”

This is one to use if you know of the person in question because she’s a big name in the industry or a leader in your company. People love flattery, and telling someone you admire her is never a bad thing. Just make sure this is someone of whom you are actually aware, because once you tell her you admire her, be prepared to explain why.

5. “I love your [e.g. an article of clothing].”

Again, flattery can go a long way. Paying a compliment, even if it’s about something small like a skirt or piece of jewelry, will immediately make her want to talk to you. Just be careful about being overly effusive; you don’t want to come off as disingenuous or creepy.

How to keep a conversation going

Opening conversation topics are well and good, but once you’ve begun making small talk with someone at a networking event, how do you keep the conversation going? If the conversation is flowing well, and your clicking with your companion, you won’t need prompts to keep it going. However, sometimes, you make need to reenergize it. Here are some ways to keep the conversation going:

6. “That’s such a coincidence! I know so-and-so, too.”

This can work for a person, an event you attended, or experience you’ve had. The point is that you want to show that you have things in common with the person. If you work in the same industry or at the same company, chances are good that you have mutual acquaintances or other commonalities.

7. “What a great story! So, what did you do?”

Show interest in what the other person is saying by asking questions. This demonstrates that you’re engaged and are enjoying talking to her. Prompting her to tell you more will show her that you really care about what she has to say.

8. “That reminds me of a book/movie/story. Have you read/seen it?”

This works especially well if you pick a book or movie that’s very popular. This way, you can segue the conversation into a discussion about something fun and entertaining. It also allows the other person to express her opinions. Just be careful not to pick a topic that’s too controversial, since this isn’t really the time or place.

9. “Can I ask your advice?”

If the person is a more senior member of the industry, she can probably share valuable insights on what to do in your career. But you can also ask a peer for advice. This is another form of flattery since you’re showing that you value her opinion.

10. “Do you want to grab lunch sometime?”

If you’re hitting it off with someone at an event, why not keep the relationship going? If you work at the same company, or your offices are in close proximity, it will be easy to grab lunch and continue your conversation later.

How to start a conversation with your boss

Perhaps you know how to conduct yourself when you expect to see your boss at meetings and other contexts, but when you walk into the office at the same time or accidentally end up in the same elevator, you freeze. Here are some conversation starters for when you run into your boss unexpectedly:

11. “What did you think of the presentation/meeting?”

What you have in common with your boss is work. Use this occasion as an opportunity to discuss a recent work situation, such as a meeting or project. Whether or not either of you played an integral role in it, she can probably find something to say about it.

12. “How’s your day going?”

Rather than asking, “How are you?”, be more specific. Ask how your boss’s day or week is going will allow her to reflect on a specific span of time, rather than life in general.

13. “I had such a strange situation today. How would you have handled that?”

As with asking advice, getting your boss’s take on how she would do something is another form of demonstrating that you value her opinion. Plus, her response might teach you another way to handle it in the future.

14. “I’ve been meaning to ask you…”

Use this as an opportunity to ask a question you’ve actually been wanting to ask your boss. Perhaps you have a question about a project or need clarification. Just avoid discussing anything you should talk about in private in a public space.

15. “Where are you going on your next vacation?”

Asking your manager a question that’s personal but not too personal allows her to talk about herself and something she enjoys doing. Travel is always exciting, so asking where she’s going next gives her a way to share something to which she’s looking forward with you.

16. “Can I have a raise?”

This is one that depends on your boss’s sense of humor and your ability to deliver it. Don’t attempt this funny conversation starter if you can’t make it clear that it’s a joke or your boss can’t take a good joke.

How to make friends at work

Starting at a new job can be challenging. As the new kid on the block, it’s difficult to get the lay of the land and develop a rapport with your coworkers. Use these conversation starters to make friends quickly.

17. “What do you do here?”

Not only does asking someone about what she does allow you to break the ice, but you’ll also learn more about the company and the different roles and positions.

18. “Hi, I’m [your name]. I’m new here.”

Simply introducing yourself is a fine way of making small talk. You’re taking the initiative to approach your new colleagues and showing that you’re a friendly person. If your colleagues are equally friendly, they’ll readily welcome you.

19. “Where are the best happy hour/lunch spots?”

Asking where people spend their time can help you get the lay of the land and learn about the culture of your new workplace. Plus, maybe your coworker will think to include you the next time she goes out.

20. “What are your tips for working here?”

If you’re talking to someone who’s been working at the company for a long time, or even just longer than you have, probably has tips for navigating your way around the workplace. Listen to them! They may serve you well.

21. “Tell me about your experience here.”

Again, this is a conversation starter that allows your coworker to talk about herself. Whether she’s had a great time or a terrible one, she’ll likely relish the chance to discuss her experience at the company. You may even learn something you didn’t know about the business.

22. “How long have you been working here?”

Whether your colleague has been here for eight months or eight years, the length of time she’s worked at the company can allow you to segue into other topics. If she’s been there awhile, you’ll be able to get her take on the company culture and management. If it hasn’t been that long, you can discuss how you’ll navigate it together.

23. “Has the company changed much?”

This is a question for someone who’s been at the company for a long time. Finding out how the company has evolved can inform you about what you can expect. You’re also flattering your colleague by establishing her as someone with knowledge.

24. “I’m a little nervous. What was your first day like?”

Your colleagues understand that first days are hard. After all, everyone’s been there. Admitting your nerves and asking about your coworker’s first day will not only help calm you down, but it will also allow you to establish common ground since she’s been in your shoes.

25. “Is such-and-such typical?”

This is a great way of learning about a new work culture as well as someone’s personality. You’ll discover what’s typical here in addition to her opinions about it.

26. “I have a terrible sense of direction. How do you get to [location]?”

It’s natural to not know your way around, and your coworker probably understands that. If you don’t know where something is, ask! If you ask a particularly friendly coworker, she might just take you there herself.

How to break the ice with your employees and direct reports

27. “Your project/presentation was terrific.”

Paying your employee a compliment on a job well done will encourage her to continue her hard work. You’re also showing that you recognize when she does well, which will make her feel good.

28. “You did a great job with such-and-such.”

Again, if there’s something in the past your employee has done particularly well, or she’s just generally doing a great job, let her know. Doing so will give her encouragement and demonstrate that you’re a manager who is invested in her employees’ growth.

29. “What did you think of the game/TV show?”

If you and your employee are fans of the same sports team or both watch a TV show, this can be a great icebreaker. Plus this gives you something fun and interesting to discuss, so you won’t have to focus exclusively on work.

30. “What did you think of the project/presentation/meeting? Would you do anything differently?”

This shows that you care about your employee’s opinion. Not only can you reflect on a work situation together, but you’re showing that you want to know what she has to say about it.

31. “How’s [name of significant other]?”

Remembering the name of your employee’s significant other shows that you pay attention to her when she talks, and you care about her as a person beyond work. Of course, you may not know the name of her partner or even if she has one, which could be an indication that you should try to get to know her better.

Don't Stress

Many people have trouble making small talk. You're not alone. Since it's something you'll encounter frequently throughout your career, the key is to practice. Chances are good you'll have plenty of opportunities.