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How to Talk With Coworkers (and Have Meaningful Conversations)

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Engaging in conversation is like a casual tennis match. Ideally, you ask an open-ended question on an interesting topic, and the other person responds with more than a one-word answer. The dialogue continues for a few rounds, and then you separate ways, hopefully with a positive feeling. 

But unfortunately, we’ve all experienced situations that weren’t that effortless, perhaps with awkward silence, one-word answers, or that left us feeling underwhelmed.

On an average day, we encounter a variety of situations that require some level of small talk—with coworkers, corporate management, vendors, or clients… So, is there a way to make this easier?

Yes! Keep reading.

Capitalize on Mondays

Mondays are a great day of the week to talk to coworkers and get to know them a little better. Why?

  • On Monday morning, people are usually fresher and rested from the weekend.
  • On Monday morning, people typically have fun topics or stories to share.
  • This can give a great start to the week

Every Monday, I ask my coworkers: 

  • How was your weekend?
  • Do anything fun this weekend?

And then take it a step further by asking specific follow-up questions. For example, with a colleague who loves sports, you may ask one of these questions and follow up using the categories above:

  • Did you see that great game this weekend? Who did you watch the game with?
    • Follow up: How do you prefer to watch games–do you talk about the plays, or is there a code of silence except for cheering in your house?
  • What did you think of that game on Saturday?
    • Follow up: Did you grow up playing a sport?
  • When did you become a fan of [insert team]?
    • Follow up: How did you become interested in that team? Are you a fan of all the teams in [insert city]?
  • Where did you watch the [insert team] game?
    • Follow up: Where did you see your in-person first game? Have you been to other in-person sporting events?
  • Why did you fall in love with that team?
    • Follow up: Were your parents as well? Were there neighborhood rivalries?

If your co-worker is a foodie, you might change it up this way:

  • Try any great restaurants this weekend? 
  • What was the best meal you ate this weekend?
    • Follow up: Is this something you cooked or had at a restaurant?
  • When is your favorite time to cook or eat out?
    • Follow up: Is there a family memory about gathering for a meal? Does your family have any traditions around food?
  • Where in the world was your most fulfilling meal?
    • Follow up: Who were you with? Why did you choose that one? Would you go back?
  • Why do you choose a specific restaurant–is it the food or the atmosphere or because it’s where your friends want to go?
    • Do you like being the restaurant chooser?

Other great breakroom questions can be as simple as following up on topics they’ve mentioned previously, like: 

  • How did your child’s team do?
  • Did you go to that new restaurant you were talking about last week?
  • What was the best part of visiting your college roommate?
  • How did your date go?
  • Do you have any fun projects you’re working on at home?
  • Did you see [insert movie title/theater performance/band name]?

Watch our video below to learn how to master small talk (and make it interesting!):

Capitalize on Friday Afternoons

Friday afternoon is another prime talking opportunity. As you head into the weekend, prime yourself for conversation success on Monday morning by listening for clues about the upcoming weekend.

  • What are you doing tomorrow that will bring you joy?
  • What was the best part of work this week?
  • How will you relax tonight?
  • What was the funniest Tik Tok you watched this week?
  • Was there something you felt good about checking off your to-do list today?
  • Any fun plans for the weekend?

Remember, you can ask about fun plans for the upcoming weekend and successes or wins from the previous week.

And during your weekends, you can practice leveling up your conversations! In this ultimate conversation course, you’ll learn:

  • How to sound confident and assertive in any conversation
  • The #1 secret of master conversationalists
  • How to gracefully end a conversation when it’s time to go
  • How to encourage People To Open Up
  • To never run out of things to say or have awkward silences again
  • …And more!

Check out our conversation course today:

Communicate With Confidence

Do you struggle with small talk? Do you often run out of things to say or feel awkward and self-conscious in social situations?

💪 Speak so people listen,
🤐 No more awkward silences,
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Start Every Conversation on a Positive Note

Sometimes, we inadvertently say something negative, like “I’m so stressed about this project,” or, “Traffic was a nightmare this morning.”

While the intent can be to avoid those awkward silences, it can be a downer as the other person starts to think about how stressed they are or their commute to work. This tone can be a bummer and set the conversation on a less-than-ideal trajectory.

Instead, start on a positive note. Think of something you can say that is more upbeat and even humorous. 

“While driving into the office today, I heard the Macarena song on the radio and cannot get it out of my head. Does that ever happen to you?”

Or with a smile, “Instead of grabbing the bag of leftovers out of the fridge, I grabbed my kid’s lunch. I guess it’s peanut butter and jelly day. What’s in your lunchbox?”

Capitalize on Common Interests

Once you find the initial nugget of common interest, capitalize on the similarity. Share something about yourself that gives your conversation partner more information about you. If you see they’re left-handed, you may say something like:

“Wow! I’m left-handed, too, and I’m so excited that I found a great tool over the weekend that made it much easier to open my tomato paste. It’s so hard to find things made for lefties!” 

You’re offering two conversation-extending opportunities by reinforcing the commonality (the left-handedness) and then talking about something specific (the tomato paste). You might end up talking about other great tools for lefties or the type of food you made and enjoyed. Either way, you’re building a rapport.

Don’t be afraid to bring up that same similarity the next time you see the person reinforce it. It extends the connection and shows the person your conversation was memorable.

Avoid Boring Small Talk With These Scripts

Rather than leaving these moments to chance, it’s helpful to have some go-to conversation starters that sound natural and effortless… and avoid the boring small talk questions. In Vanessa Van Edwards’ best-selling book, Captivate, she challenges readers to use top-rated conversation starters like these:

Instead of …Try this…
How’s work?Working on any exciting projects recently?
What do you do?Working on any personal-passion projects?
Been busy?What do you do to unwind?
How’s it going?What are you up to this weekend?

If you want to learn how to have dazzling conversations, read Chapter 3 of Captivate.

Do a Little Detective Work

While “opposites attract” may be a common phrase, researchers found that it is not necessarily the case. The similarity-attraction effect shows that we are more attracted to people with similar values, interests, and physical characteristics. We want to look for common ground and capitalize on it in conversation.

For example, if you’re in the breakroom with a colleague and both of you are filling up your morning cup of coffee, comment on the fact that you both like it. Then follow up and ask if they have a favorite roast or mention that you cannot wait for pumpkin spice latte season if that’s your jam.

If you park next to someone at the office and they’re also driving an electric vehicle, ask how long they’ve had it and what inspired them to get theirs. Ask their favorite app to find charging stations. This may lead to additional information, like whether they enjoy road trips, that will give you clues for further conversation.

Pro-Tip: Keep mental notes (or notes on your phone) about your colleagues’ interests, hobbies, and favorite topics.

Conversation Topics in the Office

One good way to overcome small talk fears is to know what to discuss in the office and what to avoid. In general, stick to neutral topics that are non-controversial at work. These include:

Best Topics

  • Family
  • Sports
  • Pop culture
  • Travel
  • Family
  • Food
  • Celebrity gossip
  • Entertainment and music
  • Current events

Controversial topics such as politics, religion, and even some current events are best left to after-hour conversations (unless you work in a newsroom or place where it’s part of the job.) Any topic that could be considered sensitive is more appropriate for conversations with real friends outside the office. 

Worst Topics

  • Finances
  • Politics and religion
  • Sex
  • Death
  • Appearance
  • Personal gossip
  • Offensive jokes

Conversation Starters for 10 Workplace Scenarios 

  1. When you’re waiting for a Zoom meeting to start

We’ve all had those remote meeting experiences where we’re waiting for someone to start the meeting, but they’re not even logged in. We don’t know whether to look down at our phones or look like we’re busy reading paperwork. Instead of staring awkwardly at others, ask a simple question to get people chatting. Consider something fun like:

  • What is the best Zoom background you’ve ever seen? (If someone has an interesting Zoom background of a tropical island, comment on it.)
  • To blur or not to blur, that is the question. Who is team blur versus team not blur?
  • Who has had their morning caffeine? If you haven’t, is that going to be a problem? (Laugh.)

Do we have any [insert team name] fans in the house? What a game…

  1. When talking to someone you don’t like

There are inevitably people you don’t care for or don’t like that you will have to talk to within the office. Instead of avoiding them completely, stick to lighter conversation topics—like the weather, sports, or pop culture–or ask for their opinion about a neutral topic. People generally feel comfortable talking about themselves.

  • How did you get to become a [job title]?
  • What are you working on these days?
  • What do you wish you had more time for?
  • Do you have a movie you’d recommend?
  • Do you collect anything?

Read 30 conversation starters with people you don’t like for more inspiration in challenging situations.

  1. As a new employee trying to understand the office culture

It’s hard to be the new kid on the block, and the faster you can become comfortable at work, the better. Developing relationships with colleagues and making work friends can help ease the transition.

After you’ve asked the most basic questions like, “What’s your position with the company” and, “How long have you been here?” you can go a little deeper to develop insights and positive work relationships with these types of questions: 

  • What’s the one thing I should know that isn’t in the employee handbook?
  • What’s your favorite tradition here?
  • What’s the secret sauce of this company?
  • Do you have any professional mentors?
  • What do you think the main takeaway would be if we were on Undercover Boss?
  • Since this is a new job, I’m looking for some good places to eat lunch that get me out of the office.
  • Do you have any favorites? 
  1. When you want to develop work friendships (and common interests)

Vulnerability and authenticity lead to openness from others. This doesn’t mean you need to share your life’s most profound moments, but giving some information about yourself can make it easier for the other person to get to know you. 

  • What’s your favorite after-work activity?  
  • How do you recharge?

These could include categories of interests, such as music and entertainment, sports and fitness, home improvement, travel, books, cooking, and other hobbies.

  • I love to play pickleball. Do you play or know anyone here who does?
  • Last night’s game was crazy. Did you see it?
  • What are you reading these days for pleasure? 
  • Have you tried those new butter boards that are so popular on TikTok?
  • I’m interested in musical theater. Do you know any local high school or college programs around here? I’d love to go and support them.
  • I heard there’s an informal company band. Where can I hear them play?
  • My partner loves cheesecake. Do you have a great recipe or suggestions for where I can buy one nearby?
  1. When a new employee joins your team

As someone who has been around the office, it can make the new person feel welcome when you try to get to know them—particularly if they’re part of your workgroup or team. Start with these types of questions to get the conversation rolling.

  • How do you prefer to be introduced?
  • Can I show you where our office has the best stash of candy?
  • How do you like to start your workday?
  • What’s your go-to beverage?
  • Do you have any questions I can answer this morning to help your day go more smoothly?

And if it’s going well and you want to know more about them, ask them to join you for lunch.

  1. As meeting (in person or remote) icebreakers

As you’re waiting for a meeting to start, you can ask questions like these to avoid that awkward silence:

  • What is one random statistic you would like to learn about this company?
  • What non-work detail would you like to know about your colleagues?
  • If you could invite a historical figure to dinner, who would it be?
  • What did you want to be when you grew up?
  • Would your classmates describe you as the teacher’s pet, class clown, most likely to succeed, or best student? And why?
  1. With someone you admire professionally

Sometimes we can get a little star-struck by leaders or meeting presenters and feel at a loss for words. Don’t be tongue-tied if you want to ask a question or find yourself walking out of the meeting room next to them. Try offering a compliment and then following up with a question.

  • The product you presented was exquisite. What inspired the design?
  • The story you told about overcoming challenges was inspirational. I’d love to hear more about your process of finding the right professional to help you.
  • That’s a great jacket, where did you find it?
  • You mentioned being involved with the [insert organization]. What inspired you to get involved there?
  • I’m impressed with how that situation was resolved. How did you come up with that solution to the problem?
  • You’ve obviously found great success in [insert industry]. I’m curious, when do you do your best thinking?
  • What is the piece of advice you’d give your younger self about how to contribute to this industry?
  1. When you’re talking to someone older

As with anyone you’re getting to know better, it’s great to ask story-generating questions that naturally lead to a follow-up. Once they answer, you could ask them to tell you more about a particular aspect or inquire about what makes it particularly exciting or challenging.

  • What was your favorite job?
  • What was your first job?
  • Who has influenced you the most?
  • What is the best piece of advice you’ve ever received?
  • What has been the most significant event in your lifetime?
  • What is one of the best inventions you’ve seen?
  1. When someone returns from vacation

When a co-worker returns from vacation, it tends to be easy for them to talk about time away. But you can encourage the conversation by asking:

  • What was your favorite part of the trip?
  • What surprised you most about the area?
  • Did you have an outstanding meal?
  • Were there any local customs you learned about?
  • How did you spend your time?
  • Would you recommend it or go back?

10. When someone returns from leave

Sometimes a coworker is out, and the reason may be unknown–perhaps it’s for an illness in the family, birth, or something else. While you may not know what to say, asking a few general questions to welcome the person back to the office and to let them know you missed them is always nice.

  • I feel like I’ve not seen you for a while (or in person.) How are things going?
  • I heard you welcomed a new member to your family. Congratulations! How is that going?
  • Is it great to have you back in the office? Is there anything you need help with this week?
  • It’s been a long time. What is filling your time these days?
  • I’m happy to see you. I’d love to hear how [insert project name] has been going.
  • I understand life has been challenging. If you are open to sharing, I’d love to hear about what you’ve found helpful in persevering.

11. When you have new conversation topics with existing co-workers 

Sometimes it feels like you’ve covered the same topics with people you see in the office daily and need something new to discuss. Try a game of this or that with our 300 Best This or That Questions for great conversations. Some of our favorites include

  • Accidental CC or reply all?
  • Heartbreaker or heartbroken? 
  • Be a polyglot or instrumentalist? 
  • Past or future? 
  • Dine alone or watch a movie alone? 
  • Snack stash or drink station? 
  • An angry boss or an angry client? 
  • Education or experience?
  • Free lunch or on-site gym?
  • Emails or meetings?
  • Notorious or unnoticed? 
  • Hero or mentor? 
  • Misunderstood or unappreciated? 
  • Loved or respected? 

Work Preferences Based on Personality Types

It’s probably no surprise that introverts, extroverts, and ambiverts (those somewhere in the middle) all communicate differently. If you can understand these nuances, you’ll have a leg up in talking with anyone in your work environment…

Preferences of Extroverts vs. Introverts at Work

Energy sourceWorking with teamsWorking alone 
Preferred processing modeOut loud, in a team meetingOn their own and then report back to the manager or team
Preferred meeting Team meetings with lots of interactionOne-on-one meetings with an agenda so they can prepare
Pre-meeting small talkLove it! They can talk to anyone.Hate it! Why talk about meaningless things?
Preferring problem-solving styleSpur of the moment with lots of ideasPrearranged with an agenda
Phone calls (yes/no)Love to pick up the phone (or, better yet, drop by) to process and solve a problem.Prefer to arrange a scheduled time to discuss, preferably with ample notice
Tips on general conversation Be patient. They may talk a lot!Be patient. It may take a while for them to open up.

Tips for Making Small Talk with Introverts

Introverts love meaningful conversations, but small talk at work can make them feel put on the spot. Set up the conversation for success by prefacing your questions with these gentle starting phrases:

  • I’m curious about …
  • I was thinking about …
  • I was wondering …
  • What do we consider a different option?

Also, recognize that their perfect weekend may mean curling up with a book or bingeing something on Netflix. Instead of asking open-ended questions, which may be stress-inducing, provide some guide rails to give them something specific to respond to:

  • What TV show are you binge-watching these days?
  • What book are you reading, or do you have any recommendations?
  • Do you have a favorite meal?
  • Do you have a pet?
  • Do you have any trips you’re dreaming about?

Are You an Ambivert? Take the Ambivert Quiz

Let’s find out how you rank on the scale. Do you think you might be an ambivert? Or do you know one in your life?

Small talk success

Remember, you can become more confident in starting conversations.

  • Be a detective. Listen carefully and ask good questions to find common areas of interest and capitalize on those.
  • Be positive. Be mindful about inadvertently beginning a conversation with a complaint. Instead, focus on smiling and starting with an upbeat note. 
  • Practice makes progress. Start conversing with strangers to practice honing your skills when the stakes are low. 
  • Use your scripts. Practice using the provided templates to help you improve these insignificant conversations, so you feel more confident when the outcomes are more important.
  • Be aware (of yourself and others). Start thinking about communication preferences and how you might maximize them to set yourself and your colleague up for conversation success.

If you liked this article and want to learn more, learn the 10 Steps to Being More Sociable to amplify your social IQ.

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