50 deep questions to ask to build strong bonds

You are the company you keep.

Every personal and professional relationship you have contributes to your life — hopefully in a positive way. Meaningful personal relationships provide belonging, community, and validation, and healthy professional connections are the difference between feeling motivated and excited about work and searching for a new job.

When people who share your interests and personal values surround you, you can collaborate more and feel well-supported to be your most authentic self. But sometimes, Zoom calls, quick text messages, and busy schedules make it difficult to connect and find common hobbies or perspectives to bond over.

To build stronger connections, we’ve provided 50 light and 50 deep questions to ask your coworkers, friends, and family members.

50 questions to get the conversation started

Building meaningful connections takes time. While some of your coworkers or new acquaintances might be receptive to diving straight into the deep end, others may feel uncomfortable answering questions that feel too personal.

And first impressions can last a long time, so it’s best to start with more light-hearted prompts. Once you’ve developed a friendship and understand their comfort level, you can move into deeper water.

The best conversation-starters are low stakes. They keep the chatter within respectable boundaries, help manage their impression of you, and let the conversation flow naturally.

Don’t feel pressured to talk about everything on the first try. After all, the objective is to create more opportunities to develop a meaningful friendship. 

Here are 50 great starter questions when befriending a coworker or developing a new friendship.

When your mind draws a blank

You may not always be on top of your conversation game. Maybe you feel tired or an important project is distracting you. Your best bet is to ask open-ended questions (those they can’t answer with a simple “Yes” or “No”) to keep the conversation flowing. And you could mention general topics that most people can relate to or provide an anecdote for. 

Here are some quick and easy conversation starters to keep in your arsenal:

1. Where did you grow up? 
2. What did you do over the weekend?
3. Did you do anything interesting over the holidays?
4. What’s your favorite hobby?
5. What’s your favorite thing about your work week? 

Work and career questions for acquaintances 

It’s best to keep some situations strictly professional. Alum events, professional association meetings, and work conferences are about building meaningful connections that boost your network.

Here are a few good questions to ask colleagues when you’re getting acquainted:

1. What did you do before working here? 
2. What projects have you been working on lately? 
3. How did you get into this line of work? 
4. What’s your favorite part of your job? 
5. What are your work pet peeves or red flags? 
6. What cool things have you accomplished in the past year? 
7. How do you like to start your day?
8. Have you read any career-related books about [your industry] lately? 
9. How do you stay organized? 
10. Do you have any go-to organization hacks? 
11. What social media do you use to promote your work? 
12. Where’s your favorite way to get into a flow state? 
13. What’s your dream job? 
14. What’s on your professional bucket list?
15. What does a perfect day at work look like? 
16. What’s a skill you’d like to develop?
17. What motivates you to work hard?
18. What’s your least favorite work task? 
19. What’s your greatest accomplishment? 
20. How do you relax when you feel stressed at work? 

“Get to know you” questions

A great strategy to engage new friends quickly is to ask them about their life. Most people enjoy talking about themselves because self-disclosure releases feel-good hormones. 

Here are some great ways to pass the mic to your conversation partner:

1. What are your favorite TV shows or movies? 
2. Do you have any pets? 
3. What’s your favorite food? 
4. Do you have a guilty pleasure musician? 
5. What’s the last great book you read? 
6. What’s the best project you’ve worked on?
7. What kind of music do you listen to? 
8. What’s your ideal holiday destination? 
9. Are you a sports fan? 
10. Are you a morning person or a night owl? 
11. Do you consider yourself to be an introvert or extrovert?
12. Do you have any personal pet peeves?
13. What’s your favorite place in the world? 
14. Who was your favorite teacher, and why? 
15. Who’s your professional role model?

Quirky icebreakers

Asking fun questions is a great team bonding method to help coworkers unwind and showcase their unique personalities. It’s also an excellent way to loosen people up in social situations with lots of new people. Icebreakers can set the tone, amp up creativity, or help everyone relax.

That said, always err on the side of caution. Stay positive, emphasize the “random” in random questions, and avoid queries that dig into someone’s personal life. 

Here are some funny questions to ask to help your team relax and share: 

1. What three things would you take if you were on a deserted island? 
2. What fictional character’s life would you like to have? 
3. What superpower would you choose? 
4. What three wishes would you ask a genie? 
5. What food would you choose if you could only eat one thing for the rest of your life? 
6. What’s the weirdest thing you’ve done for a good cause?
7. What’s the most unusual item you possess?
8. What’s your most unexpected talent?
9. If you were an ice cream flavor, what would you be?
10. If you could talk to any animal, which one would you choose?

50 deep questions for more meaningful conversations

Studies show that having deeper coworker connections can make even the most stressful or mundane jobs more satisfying. The key to work success isn’t just your performance — how you interact with coworkers is invaluable. Likewise, intimacy can strengthen your friendships, which has positive impacts on your overall life satisfaction. 

Deep questions require people to go beyond surface-level conversation. These queries prompt you to be vulnerable and self-reflect. 

Because they’re often more emotionally-loaded, remember to respect everyone’s boundaries and save more probing questions for people you’ve built a strong relationship with. That way, you’ll better understand their comfort level. 

Professional questions for coworkers

Career advancement takes a village. Throughout your professional development, mentors, coworkers, and managers have likely offered formative advice and shared meaningful experiences to help you better navigate your career path. 

Here are some questions to stimulate these sorts of valuable insights: 

1. What’s a piece of professional advice you really took to heart?
2. What’s the most important lesson you learned the hard way?
3. What have you learned about building healthy relationships at work?
4. What’s a professional deal-breaker for you? 
5. What advice would you give your younger self?
6. How have you fixed bad work habits?
7. How do you balance your work with spending quality time with loved ones?
8. What’s your biggest professional regret?
9. How do you stop comparing yourself to others?
10. What have you learned about the meaning of success? 
11. What motivates you to come to work every day? 
12. What’s your professional soulmate like? 
13. Have you ever had to make a hard ethical decision at work? What did you do? 
14. What keeps you inspired daily?
15. What’s a professional experience that pushed you out of your comfort zone?
16. Have you ever made a difficult work decision that impacted your personal life? 
17. How do you balance work and self-care?
18. Where do you draw the line in your professional life?
19. Can you share an important professional epiphany? 
20. Have you ever had to overcome a difficult professional breakup?

Personal questions that work anywhere

Creating strong social connections can make you more resilient, improve your self-esteem, and even help you live longer.

And you spend a significant amount of time socializing with your colleagues. While you don’t have to befriend everyone you work with, developing a deeper relationship beyond the professional might motivate you to bring your Whole Self to work. You might also enjoy more support and encouragement on tough days.

Here are several questions to dig deeper with a colleague you’ve become friends with:

1. What’s a childhood memory you’d like to relive?
2. Did you imagine yourself doing this kind of work when you were in high school? 
3. What are your professional dreams for the future?
4. Would you move across the country for a job? 
5. What’s the biggest risk you’ve ever taken, and did it pay off? 
6. What’s your love language?
7. What do your previous managers have in common? 
8. What’s one thing you’d change about the world?
9. How do you practice gratitude? 
10. How do you define happiness?
11. Do you have any favorite positive affirmations?
12. Do you find it easy to forgive and forget?
13. What’s one of your biggest fears?
14. If you could go back and change one thing in your life, what would it be?
15. What’s your professional philosophy? 
16. How do you cope with self-doubt?
17. What legacy do you hope to leave behind?
18. What was your most formative life experience?
19. Do you believe in having a calling?
20. How do you find purpose in everyday life?
21. How do you stay true to yourself despite outside pressures?
22. What relationship has had the most profound impact on your life?
23. Have you ever had to cut out an important colleague?
24. What’s your deepest regret in life? 
25. Do you have a “the one that got away” job?
26. How do you deal with loss? 
27. How do you approach aging?
28. What small routine makes you happiest and why? 
29. What do you wish you were better at?
30. What’s something in your life that’s both a blessing and a curse?

Kick-start the conversation

Now that you have plenty of deep questions to ask your coworkers and friends, it’s time to take that water cooler chat to the next level. 

Remember that building good work relationships and friendships takes time, consistency, and care. Don’t feel like you have to dive straight into an existential debate. Start slow, feel the connection out, and let the conversation and relationship move naturally.

Your conversations will be more interesting, and the connections borne out of them more meaningful.