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60 thoughtful conversation starters that go beyond “what do you do?”

Conversation starters don't have to be awkward.

“So, what do you do?”

Did that question make you cringe? Maybe it takes you back to that awkward dinner party where you couldn’t think of any other way to kick off a friendly chat.

We’ve all used (and heard) this go-to conversation starter plenty of times, and in professional settings, it’s impossible to avoid. At networking events, for example, it’s crucial to know a person’s job role if you want to talk about future work collaborations.

In at least one way, “what do you do?” is doing something right: As far as conversation starters go, asking questions is a great way to win someone over. According to Harvard Business School research, the more questions you ask, the more your conversation partner will like you—especially if you ask follow-up questions (which prompt the person to elaborate on something they’ve said).

In light of that research, below, I’ll offer some unique conversation starters that you can use in any work setting, including to help you spark connection with your remote team mates (since bonding virtually is easier said than done).

Let’s face it, the following questions may seem odd onscreen. In real life, nearly every conversation you have with someone new is going to begin with introducing yourself and perhaps exchanging a few pleasantries before you dive into deep questions—and that’s fine! Use your judgment on when it’s appropriate to insert these conversation starters.

With that said, let’s begin!

For networking at conferences, workshops, and meetings

What to do: Because networking is focused on making connections to further your career, keep it professional and focus on the topic of the event at hand. The great thing about conferences, workshops, and industry events is that they give you loads of topics to talk about.

What not to do: Unless you know the person well, you may want to avoid cracking jokes or trespassing into taboo territory (I’m thinking of the time a guy at a work conference asked me how much my company was paying me).

  1. “If you were to give a talk at this conference, what would it be about?”
  2. “What’s been your favorite talk so far?”
  3. “Which workshop are you most excited about?”
  4. “What’s your biggest takeaway from this conference?”
  5. “If you were in charge of this event next year, what would you change?”
  6. “What do you think is the biggest misconception about [industry]?”
  7. “What did you think about [specific speaker or workshop]?” Only ask this if you know they attended it, of course!
  8. “Tell me more about your role at [company name].”
  9. “I’m a fan of your work! [Insert specific compliment about their work.]”
  10. “If you didn’t have the job you have now, what would you be doing instead?”
  11. “What do you think of [city you’re in] so far?”
  12. “This is my first time in this city. Do you have any recommendations for what I should see?”

For other work-related social events

What to do: Social events are more relaxed, so being more playful or humorous is perfectly fine. Also, your conversations do not have to be about work!

What not to do: Don’t stick to the same group of work friends you hang out with at the office. Branch out and get to know someone new. This will stretch and strengthen your conversation skills.

  1. “What’s the best book you’ve read recently?”
  2. “I’ve been really into podcasts lately. Any recommendations?”
  3. “Have you tried the [a specific food or drink being served]? You might want to before I [eat/drink] it all!”
  4. “What exciting projects have you been working on, either at work or in your personal life?”
  5. “What do you do when you’re not working?”
  6. “What do you daydream about at work?”
  7. “When you were a kid, what did you want to be when you grew up?”
  8. “If you were invited to give a TED Talk, what would it be about?”
  9. “What’s your favorite question to ask someone when you’re trying to get to know them?”

For connecting with team members during stressful times

What to do: During times of high stress, your conversation starters might have one of the following goals: checking in on your coworker, diffusing the situation (such as with a joke), and/or getting to the root of the problem.

What not to do: Now is not the time to make assumptions or accusations. Avoid conversation starters that begin with “you’re being so…” or “why do you always…” And please, never tell someone they look tired.

  1. “What do you do to decompress these days? I’ve just been stress-eating chocolate.” That last part should be said with a smile or a laugh so they understand you’re joking.
  2. “I’m so ready for this month to be over.” This statement will convey that you’re struggling, which may give the other person the freedom to express their struggles too.
  3. “After all this, are we all gonna need a vacation or what?”
  4. “If you could wave a magic wand that would fix everything, what would your ideal life look like?”
  5. “These long workdays have been killing me. How are you handling it?”
  6. “Hey, I know it’s been rough with [the problem] going on. Anything I can do to support you?”
  7. “These are stressful times. Can I [insert specific offer to help]?” This was something my landlord said to me recently, offering to waive rent next month. Though I’d never spoken to her before, this kicked off a heartfelt conversation where we checked in with each other and were able to share our concerns.
  8. “I feel like there’s a lot of tension in the air lately. Would you like to talk about it?”
  9. “Hey, I’ve been worried about you. Are you okay?” Yes, it’s direct, but it works wonders if you want to show someone you care, particularly if you are already close to this team member.

For bonding with team members who work remotely

What to do: If it’s part of your workplace culture, make use of emojis, GIFs, or the classic “haha” at the end of a sentence to provide the emotional feedback that plain text lacks. Add as many layers of communication as you can; for example, audio is better than text, but video is even better than audio.

What not to do: Sarcasm is one of the hardest things to convey via text, so be sure to use the tools mentioned above.

  1. “Did you hear about [news-related event]? How’s it affecting the place you live?”
  2. “What’s one thing you’re excited about this week?”
  3. “What’s the weather like in your part of the world?”
  4. “We’re having an all-hands meeting next Friday. Are you joining via video?” Remote workers may feel left out when they can’t be physically present in the office. This question shows that you’re thinking of them and want to include them.
  5. “I loved [insert a project they worked on]. What was your biggest challenge in accomplishing that?”
  6. “What do you wish more people knew about you?”
  7. Share an update about the office you work in. Did your boss just install a coffee bar? Did your coworkers go on a volunteer trip last weekend? Often, remote team members don’t know what’s going on at the office. Offering a glimpse into daily office life can help them feel more in the loop. In turn, they may share what’s going on in their lives too.

Quirky conversation starters

I get it, you’re a go-getter, a rule-breaker, unafraid of straying from convention. Here are a few quirky conversation starters that will definitely make you memorable.

What to do: Be sure to use facial expressions (e.g., a smile) and a chuckle to underscore that you’re joking.

What not to do: Don’t make jokes at the expense of your conversation partner; this will likely offend them if they don’t know you. Sticking to self-deprecating humor can be a good idea.

  1. “I’m just here for the food.” Great conversation starter to throw out there while you’re piling your plate with hors d'oeuvres. Years ago, I said this to the dean of my college at a networking event. Part of me was afraid he’d find it unprofessional, but he got a good laugh out of it, and it must have left an impression because he remembered me afterward and was always helpful in my career pursuits.
  2. “What meme best describes your week so far?” This might encourage them to pull out their phone and show you the latest memes they shared and could continue into a funny conversation.
  3. “What are your views on [the Oxford comma]?” Since I’m in the writing industry, this question is specific to that. But basically, you want to put inside the brackets any issue within your industry that inspires lively debate but is actually a pretty benign topic (we don’t want to get into any fights here!).
  4. “Do you think small talk is useful? Why or why not?”
  5. “Should Pluto be a planet again? And what makes you think that?”
  6. “Is a hot dog a sandwich? Make your case.”
  7. “Do you like cats?” Judge me if you want, but I’ve used this question many times. As a cat lover, it helps me connect with fellow cat lovers. And even if someone doesn’t like cats, it’s such an oddball question that it usually solicits a laugh followed by animated discussion.

Conversation starters for introverts

What to do: If you’re an introvert, the context will matter just as much as the content of the conversation. Because introverts are often highly motivated by being in a solo environment and are more easily drained by stimulation and interactions than extroverts, try to find a quiet, uncrowded area to talk to someone one-on-one. Also, introverts often prefer meaningful conversations over small talk, so don’t be afraid to lead with a more profound question.

What not to do: Avoid trying to strike up a conversation with a large group of people. Instead of trying to chat with five people standing in a circle by the bar, keep an eye out for someone who’s on their own; you’ll feel much more comfortable approaching them.

  1. “Hi! I’m [name].” Then stick out your hand for a handshake. This is a fail-proof way to start a conversation, as the other person will naturally respond with their name. From there, you can ask pretty much any of the questions mentioned in this article.
  2. “I feel like I’ve found my fellow introverts. May I join you?” I used this exact conversation starter at a blogging conference I attended last year, and I made some friends this way! How did I know they were introverts? While everyone else was having boisterous conversations in groups by the buffet, these two were sitting quietly at a table.
  3. “Hey! Have you met [insert the name of the person you’re talking to]?” I love to use this line when I’m already having a conversation with someone, and I notice someone else standing alone. It’s a nice way to do a fellow introvert (or shy person) a favor by including them in a conversation if they don’t feel comfortable starting one themselves.
  4. “I love people-watching. Have you observed anything interesting?” 
  5. “If you could be anywhere in the world right now, where would you be?”
  6. “What’s something you’ve noticed at this event that other people may have overlooked?”
  7. “What’s one lifelong dream you haven’t yet fulfilled?”
  8. “What’s one thing you wish people would ask you about?”
  9. “When you’re having trouble sleeping, what is it that’s usually keeping you awake?”
  10. “Tell me an obstacle in your life that you’ve overcome.” I’ve got to give credit to journalist Steve Hartman for this one. For his award-winning series, Everybody Has a Story, Hartman used to throw a dart at a map, travel to the town where it landed, choose a person’s name at random from a local phonebook, interview them, and produce a heartwarming story. When he did a Q&A at my journalism school in 2010, Hartman said this was the best question to ask someone to find out what their story is.

Tried-and-true conversation starters (for when all else fails)

Why they’re useful: Yes, they’re trite, but that also means they never catch people off guard or embarrass them. They’re an easy way to segue into a more meaningful conversation. These work particularly well for total strangers.

  1. “What do you do?”
  2. “What’s your name?”
  3. “How’s your day been so far?”
  4. “What do you think of this event?”
  5. “How long have you lived here?”
  6. “Doing anything fun this weekend?”

Beyond conversation starters: How to keep a conversation going

Ask follow-up questions.

Follow-up questions are ones in which you ask your conversation partner to elaborate on something they said earlier. They show you’re actively listening and make the other person feel interesting and validated. According to the Harvard researchers I mentioned earlier, the only way you can ask a good follow-up question is if you

  • Ask an original question.
  • Listen to the answer.
  • Probe for more information.

Don’t resort to gossip.

Researcher Brené Brown points out, we often use gossip to “hot wire connection,” when in reality, it doesn’t foster true closeness.

Pay attention to tone, body language, and facial expressions as well as words.

Some people are affective communicators who rely on emotions, tone, and non-verbal gestures when they communicate. How can you tell? These people speak with their body and are often animated. Others are neutral communicators who focus on the meaning of words. They may be hard to read, so it’s important to hone in on their words, and in return, choose your words carefully.

Match your conversation partner’s communication style.

Even if you’re an expert conversationalist, we’ve all been in a situation where it feels like no matter what we say, we just can’t connect. The fact is, everyone has a certain communication style and sometimes it differs from our own, which can lead to misunderstanding.

If you’re struggling to connect with your team, take our free, evidence-based F4S assessment so you can learn the motivations and communication styles that make your colleagues tick. That way, you can match the way you communicate with the communication style of your conversation partner.

Relax, you’re doing better than you think

Armed with these 60 conversation starters, you’ll never run out of things to say (or ask) at your next networking event. Remember, the simple act of asking questions can increase your likeability; it shows you find the other person interesting (and who doesn’t like to feel interesting?). And even the most trite conversation starters—like “what do you do?”—can eventually lead to deeper, more meaningful discussion when paired with thoughtful follow-up questions.

And if you make a blunder? It’s likely no one will hold it against you. In a study published in Psychological Science, researchers found that, after we’ve had a conversation with someone, we routinely underestimate how much they liked us and enjoyed our company.

So don’t be so hard on yourself! As the study authors noted: “After people have conversations, they are liked more than they know.”

Take our free F4S assessment to learn about your (and your team's) preferred communication style.


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