33 Trust-Building Questions to Ask in the Workplace

Lori Li
15 min read
Jul 1, 2020

team-building questions

As a manager, creating a successful, cohesive team is a huge challenge. It involves a number of factors including thought leadership, proper technology, a working system, and more. 

But most importantly, it requires building trust with your team

Building trust is a common challenge every leader has to face eventually—especially when they are working with new, shy members. This challenge gets even tougher when you realize that you need to keep your employees happy, productive, cohesive, and engaged with their job in order to build an effective team.

And to make it worse, if you fail to build trust with your team, they’ll probably leave your company and cost you more money than you anticipated.

So, how then do you build an effective team?

It all starts with asking thoughtful questions at work. Because questions can start conversations, and conversations can lead to more trust and engagement—improving team productivity along the way.

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Why You Should Ask Team-Building Questions at Work

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Check this out: 93% of workers believe that the biggest factor for employee happiness is the trust they have with their bosses. 

Yet half of the employees don’t trust their supervisors and feel they’re being treated unfairly. Plus, they plan to look for a new job once the economy improves. 

So what’s happening?

Companies are failing to build a healthy work environment that benefits employee engagement, culture, team-building, and productivity that encourages their employees to stay longer with them.

There are many reasons why this is happening, including a lack of culture, poor leadership, and low financial incentives. 

Thankfully, something as simple as asking your team how they’re doing can  become a practical, helpful solution to this problem. Because having personal conversations with employees increases their sense of belonging, making it easier for them to build trust with both their team and managers.

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This practice also brings a handful of benefits:

  • Increasing the sense of belonging in employees will inevitably improve their engagement and happiness—which is key for employee retention.
  • Working in a trusted environment makes employees more confident to participate in work-related discussions and give valuable ideas and feedback—for shy people in particular.
  • When the team gets used to talking with each other, their internal communication will naturally become smoother.
  • Talking with employees can reveal information you can later use to become a better leader for them or to implement long-term improvements in the workplace (e.g., playing music  and becoming a pet-friendly office).
  • Team-building activities and games that involve answering questions work great as a way to improve employee engagement and satisfaction while getting to know your team better.

And the list goes on! 

But not all questions are the same. With that in mind, let’s turn our attention to some of the great trust-building questions you can start asking around your office.

33 Team-Building Questions Examples

I’ve compiled a list of 33 team-building questions that will help you get closer to your employees and build a trust-based relationship. 

This list is divided into three categories—personal, humorous, and work-related—to make it easier to dive into. Keep reading to learn how these questions can be used and the benefits you can expect to get from them.

Let’s jump right in.

Personal Questions

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Personal questions are great for knowing your employee’s personalities, tastes, and hobbies. They come in handy to introduce new people to the work environment and you can use them to dig deeper into your employee’s whole persona and improve your leadership skills at the same time.

1. Who inspired you to pursue the career you have today? 

This is a great conversation starter.

Knowing who and what inspires your employees will give you some useful information to improve your leadership—whether it is a motivation trigger, professional goals, or dreams.

When asking this question, see the why behind their answer and how it fits their personality. Maybe you’ve just hired the next Elon Musk and you don’t know it yet. And when you get to know how to inspire these employees, you’re not only improving performance, you’re also increasing employee engagement as well.

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2. What’s your favorite music genre?

Most people like music. So, thankfully, this question works for the majority of people.

The music we listen to can reflect our personalities. And believe it or not, talking about music can give you some ideas about the kind of person you’re dealing with (don’t be too radical on this though, there are always exceptions.)  

Keep the conversation simple and engaging. Perhaps you’ll even end up recommending some albums to each other, and who knows? Maybe you’ll end up playing some music at work, increasing productivity because of it.

3. Do you have a pet? What’s he/she like?

There’s nothing like talking about animals. You’d be surprised at how long a conversation about pets can get.

People who have pets are never afraid to talk about how they take care of their buddies. Like what kind of food they buy, how often they bathe their dog, and so on…

If you find that the majority of your team likes and have pets, you may want to consider implementing a pet policy, which can work wonders to build trust and improve collaboration between coworkers.

4. Recommend a book you recently read. 

Discovering what kind of books your employees like the most will give you some ideas about their mentality (e.g., thoughts, philosophy, and sense of morality).

Having conversations about books is extremely helpful for work—especially if you like the same kind of books and authors, which will create some sort of mental connection.

As a leader, knowing what kind of books your team likes the most will bring some opportunities to build a lecture to talk about your favorite quotes, titles, topics, themes, and more.

5. What’s your secret talent that no one knows about?

This is a great question for new members and teams since you can relate a certain person as the drummer or the chef.

It’s also helpful for delegating work. Maybe your copywriter is also well-versed in web design, so maybe letting this individual influence both the design and the copy of a new landing page may seem like a great idea.

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6. Which movie have you seen recently or what are you watching on Netflix?

We all watch movies and series.

Starting a conversation about movies or series can make them feel like they’re talking with their casual friends, so this question can work wonders to reduce some awkward or cold feelings in the work environment.

As an added bonus, you might find out about films you never knew existed. Not only will watching them help you connect with your team on a personal level, you might also learn a leadership trick or two—a double win!

7. What’s the craziest thing you’ve ever done or seen before?

This is an excellent group question to help everyone start knowing each other. And to spot the craziest, weirdest person in the room.

One of your teammates might have climbed Mount Everest. Another one might have gone bungee jumping in Austria. Someone else might have hitchhiked around South America.

Finding out what your team members are able to do will give you some useful leadership inspiration—and some joke ideas.

8. What’s the best meal you’ve ever had?

All humans are connected with food. So this question applies to everyone.

Be honest: If someone were to ask you this question, how long would it take for you to answer it? 

See, asking this question should get your employees thinking. And from there, you can start talking about what kind of food they enjoy the most—and maybe their favorite restaurants.

Everybody loves food. So having food conversations can easily engage people.

Whatever you do, just don’t ask before lunch.

9. What are your pet peeves?

With this question, you can directly find out how to be a less annoying boss.

Also, you may discover some weird pet peeves you would have never known without asking. It’s important to keep all of this information top of mind and start applying some personalized leadership.

10. Do you have traditions in your family?

This one is great if you have team members from different cultures. It helps you learn more about your teammates’ culture and history, and enrich your work environment because of it.

Also, you don’t have to come from a foreign culture to answer this question. Maybe your family likes to hike every Sunday or something like that. Any way you slice it, this question brings a lot of room for interesting conversations.

11. What was the first thing you bought with your own money?

This is an interesting question that often elicits some nostalgia. And you’ll learn about what people used to value back when they were younger.

Talking about their youth works wonders because learning about your employee’s past and how they’ve developed over time will help you learn about their drives and internal personality. Plus, it allows you to connect with them in a deeper way.

12. Is there something that has made you smile recently?

You may get some surprisingly personal answers to this question. And you’ll find yourself listening closely as your employee talks about their cat or about someone they bumped into in the supermarket.

This scenario will easily help you build a personal connection with employees. Plus, you’ll learn about their personal lives and how much attention to detail they have.

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13. What’s the best advice you can give to someone who just started their career?

This is an awesome warm-up question that helps the team start learning from each other.

You’ll get tons of great advice to apply in your life. Also, you’ll know what kind of human values are more present in your employees’ lives, such as emotional intelligence, practicality, rationality, and more.

14. What’s your favorite video/board games and why?

Gamers are becoming more popular with each passing day. And there’s a high chance that at least one of your employees is a gamer—and maybe even several of them.

If you find many gamers in your team, getting them to play together can take their collective engagement to another level. Doing so will strongly encourage friendship, which is a big deal because having close friends at work is great for increasing employee retention and enhancing company culture.

15. Do you cook? What’s your favorite recipe?

They don’t have to be top chefs to answer this question. Instead, they can just talk about what they do for breakfast and what recipes they’ve found useful and delicious.

You can create a talking point by opening a discussion about what’s the best way to cook your eggs, creating some healthy debate between people who prefer scrambled eggs over boiled eggs, and vice versa.

Humorous Questions

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These questions come in handy to “break the ice” in stressful situations where people just want to relax—which is important so that they can answer you. You’ll open some funny discussions where everyone can participate and have a good laugh together, which is good news for employee happiness and retention.

16. Pineapple pizza. Yay or nay?

This question, aside from cultivating a non-serious environment, will create some healthy discussion and disparity between people who like pineapple pizza and those who think of it as an abomination. 

(I personally think it’s great and totally legit—change my mind.)

17. What is the strangest meal you’ve ever eaten?

You’ll get some good laughs from people who have tasted exotic foreign food like tarantulas or snails. And those who have made weird mixes between spicy and sweet flavors, for example.

Whatever it is, people will feel relaxed while talking and hearing about culinary experiences.

18. What’s your weirdest habit?

If you get your teammates to tell you that they like to chew freshly mowed grass because they like the smell, then you’re getting into a dark zone of weird but hilarious true facts about your coworkers.

This can turn into a fun (and weird) conversation that only people with enough trust can have. So, this is really a good way to tell that your employees are close enough to talk about weird things without shame.

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19. Are you a beer or wine person?

This is both personal and humorous since you’re opening a discussion, plus people just find it funny or light-spirited to talk about alcohol (usually).

Also, it’s worth knowing if your team prefers beer over wine (for hosting events) and if there’s someone who doesn’t drink alcohol (which is okay, so you save yourself from getting an embarrassing no when offering a drink.)

20. What was your favorite band 10 years ago?

This question helps you spot the employee who was a My Chemical Romance emo fan back in the 2000s, and who thought that Rebecca Black’s song “Friday” was good.

People will find it funny to look at each other’s dark past and how they’ve changed over time.

21. If you had a yacht, what would you name it?

This is a pretty random question, to be sure. But arguing about what the best name for a yacht would be becomes funny and relaxing when people need to take a quick break from work and get some distraction

22. Which fictional family would you want to be part of? 

This question can open up conversations about TV shows and movies that people may like, setting the stage for an engaging conversation.

It can also showcase a little bit of the personality of each person. Someone who’d choose to be in The Simpsons will probably be different from someone who’d prefer to be a part of the Targaryen family from Game of Thrones.

23. How would you describe your job to a bunch of five-year-olds?

For a programmer or writer, it could be something like “I tap some buttons in my laptop and make money.”

This question encourages people to get creative, and when they are able to explain their job in the simplest way, it usually means that they know it well.

As Albert Einstein said: “If you can’t explain it simply, you don’t understand it well enough.”

24. Show the best meme you have in your phone.

In the internet age, we’re all connected through memes. That’s a fact.

Inviting people to show their BEST meme can give some good laughs in the workplace and will let you know what kind of humor your employees like.

Once you know their taste, you’ll be able to share appropriate memes you’ll know they will appreciate.

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25. How would you spend a million dollars in 24 hours?

Putting this challenge on your employees will give you some ideas about the things they prioritize the most—and how intelligent they are with their finances.

It’s also a fun question to ask since you’ll hear about how they’d use the money to celebrate with a crazy party, buy a Bengal tiger, or do any unnecessary but hilarious things.


Work-Related Questions

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These questions are related to the work environment and will help you know how to improve as a leader and take the company as a whole to the next level. Plus, you’ll find many opportunities to enhance employee engagement and improve retention from these kinds of conversations.

26. What’s the coolest thing you’re working on right now?

This is a great way to keep track of your employee’s progress without them feeling like they’re being constantly watched.

This question won’t only give you clues into each of the contributions the members of your team are making, it will also provide the groundwork for some well-deserved employee recognition.

For example, imagine one of your employees is combing through your image archive to clean up file names and delete duplicates. This is important work that can often go unnoticed, and that you can take as an opportunity to celebrate it with them.

27. How do you like to get feedback?

Everyone works differently. Some people like receiving negative feedback so they can improve. Others are more sensitive.

The only way to know is by asking them directly. So try to be empathetic and talk to them about how you should be giving them feedback. 

Remember that, to take your business to the next level, you need to learn how to approach your staff effectively.

If you’re worried that your employees might not be honest with you, use pulse surveys to let them share their thoughts anonymously.

28. What was your first job?

This question works wonders to help you get to know more about your employees’ backgrounds—and hear some hilarious stories.

You’ll probably hear entrepreneurship stories like how the VP of sales went from selling pencils in the street to becoming a sales professional or how the CTO started out as a hotel receptionist. 

What’s more, learning about what people needed to learn in order to reach their goals is helpful in getting your team to know each other’s strengths and weaknesses. As such, this question  can be very, very useful.

Great Leadership

29. If you could get a new skill in 10 minutes, what would it be?

This is a good way to tell what professional path your employees are aspiring for and what kind of goals they’re striving to achieve.

Also, if you’re looking to implement some training programs, you’d want to know what kind of skills your employees are interested in developing.

30. What are the toughest challenges you’ve had at work?

With this question, you’re spotting what weaknesses your employees have and can tell if they need to improve in that area or if you just need to delegate less similar tasks.

Also, you may hear some epic accomplishment stories where your employees rose to the occasion and faced a challenge successfully. This is great groundwork for employee recognition.

31. What upcoming technological innovation will dramatically impact the industry in the next five years?

As a leader, it’s good to know how your employees are thinking about the future of their industry, and if they see themselves working in it over the long term.

This question can also open discussions about technology and the industry in general, which is especially healthy for team-building.

32. What skill do you think everyone should learn?

Many people agree that the most important things aren’t taught at school.

In fact, you can change the question to “what do you wish you’ve learned in school?” to make it more specific. It could be personal finance, learning to learn, sales, and an endless amount of other topics.

This will probably turn out into a rant against the education system or the government. But at least it’s easy for everyone in the team to join the discussion and give an opinion on the topic.

The bottom line? You should learn what kind of skills your employees value the most and if it’s relevant to your business and their career. 

33. Have you taken a huge leap of faith at work? Did it pay off?

Some disciplines are not an exact science (like writing, design, and marketing). But you really need to get some results from these areas, so you’re often finding yourself taking regular leaps of faith to get them to work out (even after doing everything right).

With this question, you’ll know what were the biggest leaps your employees had to take that ended up successful. See it as an opportunity to celebrate with them and put employee recognition into practice, which—according to one of our reports—is effective when it comes to retaining high-performing employees.

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How and When to Ask Team-Building Questions

In a perfect world, you’d have plenty of social skills that allow you to connect with people and influence them. But, in reality, you still have some self-doubts and keep suffering from impostor syndrome—at least a bit.

Whether you’re a total extrovert or not, if it’s evident that you’re asking forced or previously practiced questions, the results won’t be as good as you’d like.

You need to be genuinely curious about your employees. Remember that these people are moving your company forward, and you should definitely have at least some curiosity about the people to whom you’re delegating such important responsibilities.

And once you’ve developed some honest curiosity, you can start asking questions.

As a starting point. Here are some common situations or scenarios where you can ask questions without feeling awkward:

  • At break time—when people are supposed to be talking—ask some simple questions and come up with interesting conversation topics.
  • When you need to make people feel integrated into a new environment or event (e.g., a seminar, presentation, or workshop).
  • When you want to create an open discussion where everyone can feel free to participate and give their opinion.
  • When you want to break the ice with new members or teams and start getting to know each other to reduce that awkward feeling of working with total strangers.
  • If you want to test how knowledgeable and skillful employees are in their area, ask them work-related questions and open a discussion.
  • When you need to come up with framework improvements and get more synergy, it’s important to ask employees how they prefer to work—and then fit their pieces together in order to create an unstoppable productivity machine.

If you improve your social skills, you’ll find lots of opportunities to engage your employees with conversations.

It just requires some practice and time. But most importantly...

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Be Yourself

As a favor to your company, please don’t fake these questions. 

You need to have a genuine interest in your employees and be curious about them. Because if you didn’t know, people can actually notice whether you’re being honest or putting up a facade.

Trust me: You’ll find that your employees are more interesting than you think, and you’ll surely want to engage with them. 

It doesn’t matter if they aren’t comfortable with you yet as long as you keep doing your best.

So start putting this into practice right away. You’ll see the difference. Asking the right questions will help you reveal a lot of useful information you can leverage to build an even more effective organization.



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