55 Powerful Questions to Build Authentic Connections at Work

Do you dread going to the office? Do your colleagues seem to have been born for organisational life, while you feel like a misfit?

Or maybe you love the office experience, but feel tongue-tied whenever you meet someone new?

If your modus operandi for navigating the workplace (or the world at large) is to keep your head down and talk as little as possible, this article is for you.

AND if you’re a team lead, trying to figure out how to grease the creaky conversational wheels at your next team event and build meaningful connections between employees, great news: this article is also for you!

Together, we’ll explore the basics – and benefits – of making conversation and connections in the workplace. You’ll come away with a wide range of thought-provoking questions to get to know someone, including 40 savvy team-building questions that will help you and your colleagues graduate beyond the small talk to build professional bonds that last – and make the work day a lot more fun!

So get out your hammers: it’s time to break the ice!

Why talk matters

Why should I bother? You may think as you slink past a colleague at the coffee machine. For many employees, bonding with co-workers doesn’t feel worth the effort. There are reports to finish and families to get home to. And then there are those people who simply find talking scary.

Before you roll out the excuses that you’re a loyal employee or an inveterate introvert, you should know that there are numerous perks to engaging in even the most fleeting workplace conversations.

Here’s the low down:

Talking makes you smarter

Neuroscientists have found that employees who engage in face-to-face interactions during downtime have a higher ability to learn and remember than those who don’t chit-chat on their breaks. And in another study, researchers at the University of Michigan found improvements in the brain’s executive functioning – which controls focus, planning, prioritisation, and organisation – after employees engaged in small talk. Who says talk is cheap?

Kitchen catch-ups can also bring you work benefits, for example keeping you updated on industry trends, company developments or even helpful resources.

Talking builds your network

Networking in the workplace can play a significant role in career advancement and job mobility. Conversations are an opportunity to let colleagues and leaders see your skills, dedication, and contributions, which in turn can open doors to mentorship, educational opportunities and leadership roles.

Conversation fuels creativity and innovation

Talking to your colleagues – and strangers – exposes you to different perspectives, skills and experiences, helping refine your thinking and enriching your knowledge base. And, because small talk also builds trust and connections, it can foster a more inclusive and psychologically safe workplace, which in turn boosts creativity and innovation.

Chatting makes you cheerful

We spend at least one-third of our time at work, shouldn’t we get some positives out of it?

Researchers have found that even engaging in “seemingly inconsequential” conversations can have a beneficial impact on employees’ moods and workplace experience, even enhancing their overall wellbeing. And managers should note that these benefits also extend to the organisation, bolstering engagement, productivity and workplace citizenship.

How to ask questions to get to know someone

If breaking the ice is hard for you, don’t feel bad about just diving into a conversation with “Hi there!”. Conversation starts with small talk because it has to. Think back to how you met your dearest friends – chances are good, you started off with the most obvious of introductions: “What’s your name?” “Where are you from?”

The real question is: where do you take it from there?

The easy answer is: take the person’s response and run with it. If you get nervous, remember that taking the first step in getting to know someone is already worth its weight in gold: being vulnerable fosters trust. That’s how you build authentic connections.

Naturally you also foster authentic connection by being authentic yourself. That means don’t ask questions you’re not interested in hearing the answers to. If you’re in the kitchen and find talking about coffee boring, talk about the dishes, what’s for lunch or even the weather. Small talk is just the appetizer before you get to the main course of conversational connection. With a little patience, you can use your natural curiosity and interests to get that sense of fulfillment and enjoyment that comes from getting to know someone new.

For example, if you appreciate a good cup of coffee and start with: “Have you ever worked in an office that had a decent coffee machine?” Before you know it, that gentle bashing of the office coffee machine might lead to the discovery that you both once toured the Jamaican Blue Mountain coffee roastery, or you live in the same neighborhood and adore your local cafe, or you both worked as baristas in college. Bingo! Off you’ll go into a conversational flow where you’re actually getting to know someone, not just swimming in small talk.

Breaking the ice: 15 no-fail workplace conversation starters

It’s important to be mindful of the questions you ask at the workplace. There are no-go zones for a reason. The key is to find a question that’s thought-provoking for a wide audience, yet non-invasive.

Deep down inside everyone wants to be seen for who they are, the right question will allow your conversation partner to shine by sparking their unique brand of enthusiasm and creativity. (But don’t worry, if you get a lackluster answer on your first try, just move on to the next question on the list!)

1. If you had an unlimited budget to completely redesign this room/office, what would you do?
2. Do you think of your work as creative?
3. How do you feel about technology?
4. Which technology do you use that feels the most helpful/exciting right now?
5. What’s your favorite aspect of what you do?
6. What’s your favorite spot in the office?
7. What does a perfect work day look like for you?
8. What’s your favorite workplace snack/drink?
9. What was your very first job? What did you learn from it?
10. What was your first day at the company like?
11. What’s the most helpful thing you’ve learned in the course of your career?
12. Is there anything on the horizon at work you’re excited about?
13. What do you like to do on the weekend?
14. What made you want to work here?
15. What did you study to end up in your position?

Once you’ve got a good rapport going, you can either see where the conversation leads of its own accord – maybe to the Blue Mountains! – or try out some of the more deeply thought-provoking team-building questions below.

Diving deep: 40 team-building questions to get out of the small talk-zone

We’ve all been there: finally the whole team is in one room and conversation needs a kick-start. Or maybe the team sees each other every day, so it’s hard to find juicy new topics of conversation so essential to team-building.

With the onus on team leads to set the tone and grease the wheels of communication, you may find it helpful to have some team-building questions up your sleeve designed to drive authentic connection.

Here goes:

1. What was your most spectacular or memorable moment in nature?
2. What was the best or most memorable meal you ever had?
3. What was the most memorable place you ever visited? Why?
4. What was your biggest fail or most humbling moment professionally?
5. What’s your favourite color? Why?
6. What 3 alternative careers do you dream of for yourself, and why do you find these appealing?
7. What 3 alternative roles could you see yourself in at the company and why do you find these appealing?
8. If reincarnation was a given, what would you come back as in your next life?
9. If you could bring anything to an office “show and tell” session, which of your possessions would you bring?
10. If you could teach the team something you’ve learned about (whether in leisure time or the work context), what would it be?
11. What’s your biggest ambition for yourself outside the workplace?
12. What’s your biggest ambition for yourself inside the workplace?
13. If you had to flee your home in a hurry, aside from survival essentials, what 3 personal items would you take with you and why?
14. What 3 music albums, books or movies would you want with you on a desert island?
15. If you could time travel forward or backward, what era would you visit and why?
16. What’s one thing you feel passionate about in your career?
17. What were 3 crucial or significant situations in your life where you had to make big or important decisions? Why did you make those decisions?
18. What were 3 situations in which the actions of others touched you deeply (whether people you know personally or public figures). Why did these actions touch you?
19. What were 3 situations in which you were very angry or sad? What made you sad or angry in those moments?
20. What are you good at?
21. What do you find easy?
22. What do others admire about you?
23. What situations are challenging for others, but feel easy to you?
24. At what stage of your life did your strengths become apparent?
25. How do you use your strengths particularly well for new goals and tasks?
26. When do you feel most alive?
27. When do you feel most connected to your authentic self?
28. What activities give your life a deeper purpose and how do you know?
29. Do you feel you can make a difference in the world? Why or why not?
30. What might an older version of yourself say to you about finding meaning in purpose in your life today?
31. What advice might an older version of yourself give you today?
32. What are your 3 most important goals in life that you really want to achieve? Why?
33. What’s your biggest fear professionally?
34. What does success look like to you? How will you know when you’ve achieved it?
35. What is your ideal motto to live by?
36. If you could go back and talk to your younger self, what advice would you give?
37. What are you most proud of accomplishing?
38. What would you like people to remember you for?
39. If you could live in a book, movie or tv show, which would you choose? Why?
40. What 3 qualities do you most admire in other people?

From communication to community

Getting to know your colleagues at work, even if it feels daunting at first, is a powerful way to enhance your workplace experience and personal growth. Building connections with your coworkers fosters trust, collaboration, and a sense of belonging, making the workday more enjoyable. Beyond the professional benefits, getting to know the people you spend so much time with can uncover shared interests, inspire creativity, and lead to genuine friendships that enrich your life.

While stepping out of your comfort zone might seem challenging, the rewards of forming meaningful relationships can far outweigh any initial feelings of vulnerability. Embracing the opportunity to connect with your colleagues has the power to transform your workplace into a genuine community. And we all need community to thrive.