Due to the recent rise in hybrid or remote work models, many professionals have found themselves losing touch with the intricacies of professional communication.
According to recent reports, workers and managers alike claim that miscommunication, declining social skills, and a rise in loneliness are some of the most concerning challenges brought forth by the rise of remote work.
Simply put, many of us have forgotten the skills we need to build professional relationships.
Luckily, that is something we can help with — and it all starts by learning how to start a conversation with your colleagues.
Our guide to starting a conversation at work will show you:
- Expert opinions on appropriate conversation topics in the workplace,
- 115 conversation starters for work meetings, events, and casual conversations, as well as
- 3 traits you should nurture if you want to improve your workplace conversation skills.
So, if you want to know how to start a professional conversation, read ahead!
Table of Contents
Best ways to start a conversation at work
If you want to establish a healthy work environment, you need to understand the difference between positive and negative communication in the workplace.
In other words, positive interactions can make people more engaged at work, making them better at their jobs.
Also, knowing how to find common ground with your coworkers and engage in more casual conversations in the workplace will help you:
- Gain respect and influence in your field of work,
- Establish rapport and strengthen professional relationships, and even
- Make some personal connections and friendships along the way.
So, without further ado, let’s talk about the best ways to accomplish that!
Method #1: Introduce yourself
If you’ve never met the person you want to engage in conversation with, the best way to start talking to them is to simply introduce yourself.
Corporate motivational speaker and author, Debra Fine, shares several tips for making professional introductions in her book The Fine Art of Small Talk.
The small talk expert stresses the importance of committing your interlocutors’ names to memory after giving your own name.
If you mishear or forget the name of the person you’re talking to, Fine recommends a swift confession along the following lines:
“Sorry, I’m not sure I got your name.”
“Excuse me, I’m afraid I’ve forgotten your name. Could you please remind me?”
Aside from that, Fine also emphasizes the importance of using the name we were given in its original form, advising her readers to “nix the nicknames.” To that end, she writes:
“If someone has a difficult name, make the effort to learn it — do not shorten it to a nickname without permission!”
– Debra Fine
Here’s one example of how you can double-check the pronunciation of someone’s name during a video call on Pumble, the team communication app.
Method #2: Comment on your surroundings
Commenting on one’s surroundings or general circumstances is a fairly safe place to start a conversation.
That’s why the weather and current events are among the most used topics to talk about with coworkers.
Then again, these kinds of conversation topics can seem a bit uninspiring to those seeking a deeper connection. That’s why this method is mostly used by people just starting to learn about their coworkers.
For them, making casual comments about what they had for lunch or that someone left doughnuts in the break room can be a good way to set everyone at ease before segueing into more substantial topics.
Method #3: Discuss pop culture or industry news
Once you learn a thing or two about your coworkers, you can start testing the waters with some more interesting small talk topics for work.
If you’ve already discovered that the person you want to approach is interested in a particular genre of movies, you can use an opener that reflects that.
Otherwise, you could always mention an industry trend and start a conversation that way.
This method is also the perfect place for us to incorporate more of Debra Fine’s advice.
According to the small talk expert, the best workplace conversation starters are a combination of a statement and a response prompt.
So, instead of just saying, “Generative artificial intelligence is changing the way we work,” you could add:
“How do you think gen AI will affect our industry in the next 5 years?”
Of course, this tip should work just as well — if not better — with more casual topics of conversation.
Then again, if your company uses a business messaging app to facilitate collaboration, you should know that those casual conversations should be kept separate from the rest of your work-related discussions.
Depending on your company policy and the permissions you’ve been granted as the user of the app, you may be able to create new channels to host the types of conversations you’re hoping to have with your coworkers.
As an example, you could create a #recommendations channel to discuss your favorite movies, music, and books.
Method #4: Ask for help or offer to help
According to a career coach, therapist, and member of the Forbes Coaches Council, Jessica Sweet, starting a conversation by asking for help is a great way to connect with the people you work with:
“One of the best ways to start a conversation at work with someone you don’t know is to ask for a favor.
The ‘Ben Franklin Effect’ is the idea that people like you more when they do you a small favor.
So, start a conversation by thinking of a small ask, and then dive into [other topics].”
The key to using this method to start a conversation with someone you work with is to make sure what you’re asking for isn’t too time-consuming.
After all, the ask itself is only the beginning of the conversation, so even something innocuous will do the trick. To illustrate that point, let’s look at the example below.
Method #5: Ask questions
If you’re not satisfied with superficial conversation starters, you can create deeper connections with the people you work with by asking more substantial questions.
In her book, Debra Fine suggests using open-ended questions and statements such as:
“Why?”
“How did you…?”
“Could you describe…?”
“I’d love to learn more about…”
“What was that like for you?”
“What brought you to…?”
Of course, you wouldn’t want to sound like you’re interrogating your interlocutors.
To avoid that, be sure to offer some information about yourself before asking the other person any questions.
Even then, you should stay in the realm of appropriate topics of conversation in the workplace. If you’re not sure which ones would fit the bill, executive public speaking coach, bestselling author, and international speaker, Karen Donaldson, has the answer.
“Appropriate conversation topics for work include the company, the work that you do there, and accomplishments. On a non-invasive personal level, you can discuss leisure time activities, hobbies, vacations, upcoming holidays, and weekend plans. When you go into the territory of asking non-invasive personal questions, people start to build relationships with one another.”
However, the confidence coach also noted that sometimes, the people we approach with a conversation starter may be reluctant to share. So, we should expect and accept that, as the example below indicates.
Method #6: Give a compliment
Most people believe that being complementary is one of the safest ways to start a conversation in the workplace.
However, the broader context and the exact wording you use can make or break your chances of having a pleasant and, more importantly, respectful interaction.
With that in mind, you should only follow one steadfast rule when complimenting someone you work with — or, really, anyone you don’t know that well.
Namely, you should avoid commenting on body parts, at least anything that isn’t a conscious choice. That exception should still allow you to tell a coworker that their new hair color looks nice.
But, to be safe, you should try to restrict yourself to praising professional achievements rather than physical attributes, as career and business coach, Corbet Fawcett, told us:
“Be cautious of inappropriate comments and microaggressions. What seems like an innocent compliment may have negative implications. When in doubt, keep it professional. Focus on the work, not the person.”
According to Jessica Sweet, it’s all about making the other person feel appreciated:
“Compliment their work, the quality of their questions or observations, or their work ethic. You want to keep it professional, and noticing what they do, how they do it, and the impact it has can go a long way in making someone feel seen and appreciated.”
Here’s one example of what providing that kind of employee recognition might look like.
Method #7: Tell a joke
At this point, you may have noticed a progression on our list of methods you can use to start a conversation at work.
Essentially, the workplace conversation starters in the first half of our list would allow you to strike up a conversation with any passing acquaintance. Meanwhile, the methods we have introduced in the latter half would work better on coworkers you were more familiar with.
So, what does that tell us about using humorous conversation starters at work?
Basically, you should limit their use to people you already know fairly well.
After all, even professional comedians can never be sure about the types of jokes that will “land” well with their audiences. The only way you can be reasonably sure that your joke won’t offend anyone is if you know your interlocutors’ preferences.
On top of that, you should also consider your hierarchical position within the company.
Even though having a sense of humor is seen as an advantage for those in leadership positions, recent studies have shown that employees can feel pressured to appear entertained when leaders use humor excessively.
Having to perform this way can exacerbate emotional exhaustion and meeting burnout, leading to decreased job satisfaction in workers.
So, if you’re participating in an act of downward communication, be sure to take that into account before starting a workplace conversation with a joke.
Method #8: Send them a direct message
In bygone days, most people would have felt that using conversation starters at work was limited to the short breaks away from their desks.
Luckily, that is no longer the case, as communication can be achieved anywhere, even from the comfort of one’s cubicle, thanks to various team communication tools.
According to Karen Donaldson, the transition to remote work models has negatively affected the level of closeness we can achieve with our coworkers:
“One of the challenges when working on a remote team is that people feel like they don’t know each other and there is less camaraderie.”
Of course, with this kind of workplace communication, knowing how to balance work-related communication and chit-chat is key.
In an office environment, you can see which of your coworkers are interested in small talk by examining the nonverbal cues they send.
However, when the only thing you see is your coworkers’ virtual presence, you have to rely on:
- Their usual personality (keeping in mind that everyone can have good and bad days),
- Their availability status (as seen in the image below), or even
- What their workload looks like (which you can check on the time or task management software your company uses).
💡 PUMBLE PRO TIP
Texting people during their lunch break can be a faux pas, especially if you’re not friends on a personal level. To learn more professional messaging etiquette, check out this article:
Bonus tip: Avoid controversial topics
The success rate of conversation starters that rely on questions, compliments, and jokes usually depends on their delivery, wording, and central topic.
Since that last condition is particularly important, we asked experts to share what they believe are the topics everyone should steer clear of in the workplace.
Karen Donaldson put it simply:
“Avoid conversations about race, religion, and politics — especially if it is not integral to your job.”
And, Jessica Sweet agreed, adding that certain topics can spark difficult conversations:
“Avoid other people’s appearance as well as controversial topics such as religion and politics. These things tend to lead to difficult conversations that need to be handled carefully and can go bad easily. If they do go bad, you still need to work with the other person. It’s best to avoid these altogether.”
When in doubt, you should stick to either work-related topics or your personal life outside of work — as long as the person you’re talking to seems open to discussing the latter.
115 Best work conversation starters for any occasion
Having shared experts’ opinions about the best conversation starters to use at work, it’s time to finally see their tips in action.
Some of the examples we’re about to list are from Debra Fine’s The Fine Art of Small Talk, while others are sourced from all over the Internet (as well as the collective experience of anyone who’s ever had a casual conversation at work).
Now, we’ve decided to break up our compilation into the following categories:
- Basic and neutral conversation starters for work,
- Work-related conversation starters,
- Career-focused conversation starters,
- Observational conversation starters for work meetings, events, or conferences,
- Entertaining team conversation starters inspired by pop culture,
- Quirky and humorous conversation starters for coworkers, and
- Seasonal or holiday-related conversation starters for work.
Naturally, not all of our examples will apply to your current situation. Still, you should be able to find plenty of phrases you can use in person and on your company’s internal communication software below.
Category #1: Basic and neutral conversation starters for work
The first category of workplace conversation starters we have compiled consists of the basic statements and inquiries you might use to start a casual conversation at work.
Without further ado, let’s see some examples of conversation starters for coworkers, employees, and managers alike!
“Hey, [name]! How’re you doing?”
“How’s your day going?”
“What are your plans for this weekend?”
“Did you do anything fun last weekend?”
“How’re the kids?”
“How’s your partner/[insert partner’s name to personalize prompt]?”
“Do you have any pets?”
“How’s your dog doing? Is she free of the cone of shame yet?”
“What do you do in your spare time?”
“I’m headed to a painting class after work. How about you? Do you have any hobbies?”
“What are the best lunch spots around here?”
“What are you thinking about having for lunch?”
“Should I get pasta or pizza? I haven’t tried either of those here.”
“I’m off to get coffee, would you like to join me?”
“Hey, want to go out and do some people-watching during our break?”
“The weather is so nice today, I wish we could have a picnic right now.”
“You won’t believe what just happened to me on the way to work…”
“Wow, my brother loves quirky socks, too! Where’d you get those?”
“That’s a really nice bag! Can you fit your laptop in there?”
“My phone has been so buggy lately, I’m thinking about getting a new one. Are you happy with yours?”
💡 PUMBLE PRO TIP
If you ever find yourself at a loss for a reply to one of these basic questions, this article might help:
Category #2: Work-related conversation starters
If you’re wondering how to start a conversation with colleagues you don’t know well, work-related topics are your best bet.
With that in mind, here are some work-related conversation starters.
“How’s that report coming along?”
“How are you managing your workload?”
“Do you need any help with that task?”
“What’s your passion project right now?”
“Are you working on anything exciting lately?”
“What was the highlight of your week/day?”
“What did you think about what we discussed during that meeting?”
“Do you usually prefer virtual meetings or in-person ones?”
“I really liked your presentation about [topic]!”
“That was such a great idea — how did you come up with it?”
“Did you read any books while preparing to give your presentation?”
“I’m a bit nervous about the task I was assigned. Have you ever done something like it before?”
“Could you recommend some resources for improving public speaking skills?”
“What do you think will be the next trend to take the industry by storm?”
“Have you heard about the latest industry trend making the rounds?”
Category #3: More career-focused conversation starters
Our next category of work conversation starters consists of prompts you can use to gain a deeper understanding of your coworkers’ career trajectories.
So, rather than inquiring about your interlocutors’ current workloads, these questions would be more suitable for interviewing mentors, managers, or senior colleagues.
If you find those kinds of interactions invaluable, here are the best ways to get the conversation started.
“What’s your favorite thing about your job?”
“What are the best and worst jobs you’ve ever had?”
“How did you become interested in your field of work?”
“What would you say has been your most important work experience?”
“Do you have any professional regrets you wish you could go back and change?”
“What are some of the skills or experiences you’ve found valuable in your career?”
“So, how long have you been with the company? I’m really interested in your career path.”
“What upcoming trends could you see impacting our industry? How would you stay on top of those changes?”
“What resources or opportunities would you recommend to someone looking to advance in this field?”
“I’d love to learn more about [specific department, project, or topic]. Could you share some of your insights on the topic or perhaps connect me with someone with relevant experience?”
💡 PUMBLE PRO TIP
Usually, the people who educate junior employees about the current state and future trajectory of the industry are older employees. With that in mind, improving workplace communication across generations could be beneficial. This article is sure to help:
Category #4: Observational conversation starters for work meetings, events, or conferences
Some of the workplace conversation starters we have already listed have observational elements.
However, in this category, we’re going to focus on casual remarks you can make at work events or conferences.
“Have you ever been to a work event before? Did you have them at your previous job?”
“Isn’t it strange seeing everyone in person like this? I’ve gotten so used to seeing y’all through a screen!”
“They really went all out with the decorations, didn’t they? Did you see the flower arrangements?”
“What an amazing venue! I hope they keep booking it.”
“Have you tried any of these cocktails/appetizers?”
“All the food looks so good… I’m not sure what to pick. What are you thinking of getting?”
“I’d love to try this cake, but I don’t think I could eat the whole piece. Would you split it with me?”
“Have you heard the news? Apparently, the company is looking to bring in more people to the PR department.”
“Did you bring a plus one?/Who have you brought with you today?”
“I hear the DJ is taking requests. Should we go suggest a song?”
“Wow, it’s like a dance battle out there! Who do you think is winning right now?”
“Can you believe Jim is retiring? I remember one time he [tell anecdote].”
“What did you think about Darla’s speech?”
“Which workshop are you most excited about?”
“Would you ever want to hold a workshop here? What would it be about?”
Of course, many of these prompts can be used outside of in-person get-togethers, as evidenced by examples of workplace conversation like the one below.
Category #5: Entertaining team conversation starters inspired by pop culture
If you want to start a conversation in the workplace with someone you already have an established rapport with, you’ll be able to discuss more entertaining conversation topics.
“What’s your favorite movie?”
“Are you watching anything good on TV?”
“Which streaming services are you subscribed to?”
“This video is cracking me up, check it out!”
“Have you seen that TV show/basketball game/news segment?”
“Do you listen to any podcasts?”
“Would you say that you have any niche interests?”
“Have you played this card/board game?”
“Who’s your favorite author/musician/celebrity?”
“What kind of music do you listen to? What’s on your playlist?”
“Do you prefer listening to live music or listening to albums?”
“What was the first concert you went to?”
“When you realize you’re watching a bad show, do you stop or do you push through?”
“This might be my new favorite book. Do you have a favorite?”
“Which celebrity do you think is most likely to be an alien?”
“Did you read about that actress’s fitness routine? Wild. When does she sleep?”
“They’re giving that author a lifetime award. What would you want to be remembered for?”
“Have you seen how that celebrity reacted when they were on that prank show? How do you think you’d react if you were pranked like that?”
“Yikes, they’re making a gritty reboot of another animated classic. Place your bets, which one do you think it is?”
“If you could make everyone you know listen to a song/watch one movie/read one book, which one would you choose and why?”
Category #6: Quirky and humorous conversation starters for coworkers
Once you get comfortable with the people you work with, you’ll be able to have more fringe conversations with the help of the following workplace conversation starters.
“Do you have any secret talents?”
“If you were a ghost, who would you haunt?”
“Which superpower would you like to have?”
“If you could max out a skill with a cheat in real life, which one would you choose?”
“If you could get a hypnotist to remove one of your flaws, what would it be and why?”
“Do you have any items you’ve saved from childhood?”
“What’s the most fun you’ve ever had?”
“What would you title this chapter of your life?”
“What’s the silliest thing you’ve ever seen an animal do?”
“Do you think you could survive a zombie apocalypse? What would you do if it broke out while we were at the office?”
“Let’s say everyone in the office is cast in a heist movie. Who has which role?”
“If your life was a TV show, what genre would it be? What would be the opening credits song?”
“What would you do if you had all the money in the world and all your needs were taken care of?”
“I just found out that Australia was at war with emus in the 1930s, and the emus won. Isn’t that crazy?”
“What mindblowing facts have you learned recently?”
💡 PUMBLE PRO TIP
If you want to have casual conversations on your company’s internal messaging software, make sure you keep them in dedicated channels. Learn more about that particular feature here:
Category #7: Seasonal or holiday-related conversation starters for work
Throughout the year, many significant events come with the changing of the seasons.
The following work conversation starters should cover everything from summer vacations to holiday greetings.
“How do you feel about New Year’s resolutions?”
“What were your resolutions last year? Did you achieve your goals?”
“Do you have any plans for Valentine’s Day?”
“My friends are going to an Irish pub for St. Patrick’s Day. Do you celebrate?”
“Are you going to travel this summer? What’s the coolest place you’ve ever been to?”
“Do you have a place you’ve visited that you hope you never go back to?”
“What’s the best vacation you’ve ever taken?”
“How was your vacation?”
“What are you doing for Thanksgiving?”
“Do you like having family gatherings?”
“What was the best Halloween costume you’ve ever put together?”
“Are you looking forward to the holiday season? What’s your favorite holiday?”
“Are you going back to your hometown for the holidays? What’s it like there?”
“I love rainy days! What’s your favorite thing to do in this kind of weather?”
“I’m trying to find this toy my kid requested for Christmas, but it looks like it’s sold out everywhere! Where do you shop for your kids’ presents?”
“Are you done with your holiday shopping yet?”
“What a year! What was the highlight for you?”
“Do you do any winter sports? Have you tried skiing or snowboarding?”
“Do you have any family traditions you’ve decided to bring into your household since you’ve had kids?”
“I love the smell of pine; it really makes me get into the Christmas spirit. Do you have any scents that bring back memories?”
3 Traits that make workplace conversations easy
Before we wrap up, we’d like to point out that the successful delivery of these work conversation starters largely depends on the speaker’s social aptitude.
Luckily, those looking to become effective communicators in the workplace (and beyond) will be pleased to learn that that particular skill can be honed.
In fact, to break it down further, there are 3 traits you can work on if you want to learn how to initiate a conversation successfully.
Trait #1: Attentiveness
Arguably, the most important trait you can bring to a workplace conversation is attentiveness.
As Karen Donaldson told us, this trait will allow you to build and navigate relationships at work more easily:
“First of all, only start a conversation if you’re willing to be an attentive listener. Then, keep things simple. Start with something relatable to both of you (the company, the job). When you want to build relationships with your co-workers, you want to go beyond work while respecting people’s privacy.”
For(bes) The Culture Council Member, creative communication, and DE+I expert, Anna Taylor, also mentioned the importance of developing active listening as a skill:
“The best way to show you’re interested in what a coworker has to say is to practice active listening. Active listening is a communication skill that involves going beyond simply hearing another person’s words but also seeking to understand the meaning and engaging beyond short responses.”
Meanwhile, Jessica Sweet noted the importance of body language, saying:
“It’s surprising how many people let their minds (and eyes) wander while someone else is speaking. Show that you’re interested by listening, keeping your eye contact appropriately on the other person, and asking relevant questions.”
Essentially, being fully engaged in a conversation is a great way to show respect and genuine interest in your conversational partner(s).
On occasion, the practice of attentive listening may also require us to exercise other skills, such as emotional control and empathy.
Trait #2: Positivity
Some people might suggest that a good way to bond with the people you work with is by sharing common complaints.
To that end, many people will take the opportunity to mention the broken coffee machine in the break room or disparage an annoying coworker as a means of starting a conversation.
However, it’s best to keep such negative statements to a minimum, particularly when initiating workplace conversations.
After all, you wouldn’t want to become known as the company’s resident Debbie Downer.
Take it from communications consultant, Jana Lynne Sanchez:
“Be authentic. If you don’t like something, don’t mention it. There is something likable about most people. Find it and mention it.”
💡 PUMBLE PRO TIP
If you are dealing with difficult people at work, practicing your communication skills with them will serve you much better than badmouthing them in front of other coworkers. This article should help you find a way to talk to all manner of challenging colleagues:
Trait #3: Confidence
Becoming more confident can be a huge help when initiating conversations in the workplace.
However, some people mistakenly equate confidence with arrogance — which happens to be one of the worst conversational sins, according to author Debra Fine.
In fact, many of the conversational faux pas Fine mentions in the Crimes and Misdemeanors chapter of The Fine Art of Small Talk could instead be seen as coming from a lack of confidence.
A person who is unsure of themselves might:
- Interrogate their interlocutors,
- Brag about their accomplishments too much,
- Interrupt or try to one-up others in conversation, and
- Monopolize conversations under the pretense of keeping the ball rolling.
Conversely, true confidence means seeing the worth of your accomplishments and understanding your shortcomings — and being willing to work on them.
From that perspective, we can imagine that a truly confident person would be able to:
- Avoid oversharing,
- Laugh at themselves rather than mocking others,
- Acknowledge other people’s efforts and achievements,
- Keep a friendly demeanor through expressions and body language,
- Ask meaningful questions and show interest in the answers, and ultimately
- Initiate workplace conversations more easily.
Connect with your coworkers on Pumble
Establishing genuine connections through banter can make even the most tedious days at work much more enjoyable.
But, if circumstances prevent you from having pleasant conversations with your coworkers in person, using team communication apps like Pumble is going to be the next best thing.
As our workplace conversation examples show, Pumble lets its users communicate through:
- Direct messages,
- Private and public channels, and
- Threads.
Best of all, everything you send will be saved forever, due to Pumble’s unlimited messaging history, and easily accessible, thanks to the app’s search feature.
Still, if text messaging doesn’t quite cut it, you can also exchange voice and video messages or even have voice or video calls with your team.
And, if you’re lacking conversation partners, you can even invite external guests and give them roles and permissions to make them feel at home at your organization’s workplace.
Communicate more effectively with Pumble — try it now!
