330 Questions to Ask in a Coffee Chat (Sip ‘n’ Speak Guide)

Coffee chats are like little windows into new worlds. They’re relaxed talks where you get to learn about people, their dreams, their work, and so much more. 

But what do you talk about? How do you start? The right questions can turn a simple chat into an exciting journey of discovery. So grab a cup of your favorite brew, and let’s explore some questions that can make your next coffee chat a memorable one.

Questions To Ask About Personal Interests

  1. What do you enjoy doing in your free time?
  2. Have you traveled anywhere recently?
  3. Do you have any favorite hobbies or pastimes?
  4. What’s your favorite type of music or band?
  5. Have you read any good books lately?
  6. What’s your favorite way to relax on the weekends?
  7. Do you like to cook or have a favorite dish?
  8. Are you into any sports or outdoor activities?
  9. Have you seen any great movies or shows recently?
  10. What’s your favorite place you’ve ever visited?
  11. Do you enjoy any creative arts like painting or writing?
  12. What got you interested in your current hobbies?
  13. Do you have any pets?
  14. What’s something you’ve always wanted to learn or try?
  15. How do you usually spend your holidays?
  16. Do you have a favorite childhood memory?
  17. What’s something that makes you really happy?
  18. Do you have any fun plans coming up?
  19. What’s your favorite season and why?
  20. How do you feel about social media and technology?
  21. What place have you never visited but would love to visit?
  22. Do you prefer spending time indoors or outdoors?
  23. What’s your favorite way to spend time with friends or family?
  24. Have you ever tried any unusual hobbies or activities?
  25. Are you a morning person or a night owl?
  26. What’s the most adventurous thing you’ve ever done?
  27. Do you have a favorite quote or saying that inspires you?
  28. What’s something you could talk about for hours?
  29. If you could meet anyone in history, who would it be and why?
  30. Do you have any hidden talents or skills?
  31. How do you like to celebrate your birthday?
  32. What hobby or interest do you want to get into but haven’t yet?
  33. Do you prefer watching TV shows or movies?
  34. What’s a piece of technology or gadget you couldn’t live without?
  35. Are you a fan of any particular sports teams?
  36. How do you handle stress or unwind after a long day?
  37. Do you have any favorite family traditions?
  38. What’s your favorite way to stay active or fit?
  39. If you could have any superpower, what would it be?
  40. How do you feel about current fashion trends?

Questions To Ask About Work

  1. What do you do for work?
  2. How did you get into your current field?
  3. What do you enjoy most about what you do?
  4. Are there any big projects coming up?
  5. Do you have any mentors or people you look up to in your field?
  6. What’s the biggest challenge you’ve faced in your work?
  7. What’s something you’ve recently learned that excites you?
  8. Do you participate in any work clubs or groups?
  9. How has your career path changed over time?
  10. What’s your dream job or ultimate goal in your field?
  11. How do you handle stress or pressure?
  12. What’s something that surprised you about your work?
  13. How do you keep up with changes or news in your field?
  14. What are some misconceptions people have about your job?
  15. How has your work affected your personal life?
  16. Do you have any recommendations for resources, such as books or websites, related to your field?
  17. What are some emerging opportunities or challenges in your industry?
  18. What are some interesting projects or research you are currently working on?
  19. What’s the most challenging decision you’ve made in your career?
  20. What unexpected skills have you picked up in your work?
  21. How do you foster a positive and productive working environment?
  22. What’s the best way to stay organized and on top of your responsibilities?
  23. How do you measure success in your work?
  24. What are your favorite tools, apps, or resources for work?

Questions To Ask In A Networking Coffee Chat

  1. How did you get started in your career or field?
  2. What’s your current role, and what does it entail?
  3. How do you approach networking and building connections?
  4. Do you have any advice for someone looking to get into your field?
  5. What are some of your professional goals or projects?
  6. What’s a typical day like for you?
  7. Are there any events, conferences, or groups you recommend?
  8. What’s the most rewarding part of your job?
  9. How has networking helped you in your career?
  10. What’s a challenge you’ve overcome in your career?
  11. How do you stay motivated and passionate about what you do?
  12. What are some skills you think are vital in your field?
  13. Can you tell me about a project you’re particularly proud of?
  14. What are some mistakes you’ve learned from in your career?
  15. How do you continue learning and growing professionally?
  16. Would you be open to staying in touch or meeting again in the future?
  17. What’s the most rewarding collaboration you’ve had in your career?
  18. How do you approach professional challenges, and can you share an example?
  19. Can you recommend any professional groups or associations related to our field?
  20. How do you see our industry evolving over the next 5 to 10 years?
  21. What’s the most interesting project you’re working on right now?
  22. How do you decide what conferences or professional events to attend?
  23. Can you share a time when networking really made a difference in your career?
  24. What skills do you think are most underrated in our field?
  25. What are some of the core values that guide your professional decisions?
  26. How do you manage professional relationships and stay in touch with contacts?
  27. How do you continue to learn and grow in your field outside of formal education?
  28. Can you share some success stories from your career that might inspire others?
  29. What’s your process for evaluating new opportunities or career paths?
  30. How do you find a balance between professional growth and personal well-being?
  31. What are the most effective ways you’ve found to promote yourself or your business?
  32. How do you approach mentoring others?
  33. Have you had any rewarding experiences as a mentor?
  34. What’s your perspective on the current job market in our industry?
  35. What advice would you give to others in our field regarding work-life balance?
  36. What’s your perspective on social media and online networking platforms, and how do you utilize them effectively?
  37. Are there any upcoming events or conferences in our field that you’re looking forward to, and why?

Questions To Ask About Future Goals And Dreams

  1. What’s the biggest dream you have for yourself?
  2. What steps are you taking to achieve it?
  3. How do you envision your life in 10 years, both personally and professionally?
  4. What smaller, short-term goals are leading you toward your larger aspirations?
  5. How do you handle setbacks or obstacles when pursuing your dreams, and can you share an example?
  6. What people or resources inspire or guide you in pursuing your goals?
  7. How do you find the balance between dreaming big and setting realistic and achievable goals?
  8. What’s a goal or dream you had in the past that you’ve either achieved or adjusted?
  9. What did you learn from the process?
  10. How do you ensure your daily actions and decisions align with your long-term visions?
  11. Are there any risks you’re considering taking to pursue a dream
  12. How are you evaluating them?
  13. How do you measure success in the context of your future goals?
  14. What does success look like to you?
  15. What role do mentors or role models play in shaping and supporting your future aspirations?
  16. How do you stay motivated and focused on your goals, especially when progress is slow or challenging?
  17. How do you approach your personal development and growth as part of pursuing your dreams?
  18. Are there any societal or external pressures that affect your goals, and how do you navigate them?
  19. What’s something you hope to learn or master in the future, and why is it important to you?
  20. How do your friends and family support or influence your pursuit of your dreams?
  21. Are there any ethical considerations or values that guide your choices in striving for your future goals?
  22. How do you prioritize your various goals, especially when they conflict or compete for your time and energy?
  23. What’s a dream or goal that scares you a bit, and what makes it both challenging and exciting?
  24. How do you envision giving back or contributing to others as part of your future aspirations?
  25. How do your current hobbies or interests tie into your future aspirations?
  26. If you could spend a day with anyone who’s achieved a goal similar to yours, who would it be, and what would you ask them?
  27. What goal have you set that requires collaboration with others? 
  28. How are you building those relationships?
  29. How do you keep track of your progress toward your dreams?
  30. Do you have any rituals or routines to help you?
  31. In pursuing your dreams, how do you ensure you’re also caring for your well-being and personal needs?
  32. Who do you turn to for honest insights?
  33. What future goal do you feel is unconventional or unique to you, and what draws you to it?
  34. How do you reconcile differences between your goals and the expectations or wishes of those close to you?
  35. What role does financial planning play in your future dreams, and how are you approaching it?
  36. How do your future goals reflect the legacy or impact you want to leave behind?
  37. How do you handle the fear of failure or rejection as you work towards your goals?
  38. What recent accomplishment has brought you one step closer to your larger dream, and how did it feel?
  39. How do you ensure that your goals and dreams remain flexible as your life and circumstances evolve?
  40. How do you celebrate milestones or successes along the way to your bigger aspirations?
  41. Are there any travel experiences or cultural explorations tied to your future goals, and how do they fit in?
  42. How do you find joy and fulfillment in the journey itself, not just the end goal?
  43. What’s a question you often ask yourself as you reflect on your future, and how do you answer it?

Questions To Ask In A Coffee Chat With Employees

  1. How did you find your way to this company?
  2. What attracted you to your current role?
  3. What’s your favorite part of your job?
  4. What keeps you motivated?
  5. Can you share an example of a project or task that you found particularly rewarding?
  6. How do you handle challenges or obstacles in your work, and can you describe a situation where you overcame one?
  7. What opportunities for learning and growth have you discovered here?
  8. How has the company supported you in that?
  9. What does the company do to facilitate work-life balance?
  10. What’s the team dynamic like?
  11. How do you contribute to a positive and collaborative environment?
  12. How do you stay up-to-date with new developments in your field? 
  13. Does the company provide any resources or support?
  14. Can you describe the relationship between your team and other departments and how you collaborate on shared goals?
  15. How do you approach giving and receiving feedback? 
  16. How does that fit into the company culture?
  17. What’s something unique or special about the company culture that might not be immediately apparent?
  18. How do you prioritize your tasks and manage your time effectively, especially during busy periods?
  19. Can you share a fun or memorable experience you’ve had with your colleagues outside of work?
  20. How have you seen the company respond to employee feedback or concerns?
  21. How do you see your career progressing within the company?
  22. What opportunities are there for advancement?
  23. What do you wish you knew when you started working here? 
  24. What advice would you give to a new hire?
  25. How does the company’s mission or values resonate with you personally?
  26. How do you see them reflected in your work?
  27. How do you approach creativity and innovation in your role?
  28. How is that encouraged within the team?
  29. What personal or professional goal are you currently working towards?
  30. How are you approaching it?
  31. How do you feel the company supports community engagement or social responsibility, and have you been involved in any related initiatives?
  32. How does the company encourage continuous improvement?
  33. What have you done to embrace this philosophy in your role?
  34. Can you share an instance where you made a positive impact within the company or community through your work?
  35. How do you find inspiration when faced with a creative challenge or a new project?
  36. How do you build and maintain relationships with clients or external partners?
  37. How have you seen the company adapt and change during your time here?
  38. What’s been your role in that evolution?
  39. What kind of volunteer or philanthropic efforts does the company participate in?
  40. Have you been involved in any of these?
  41. How does your team celebrate successes or milestones, and can you share a memorable celebration?
  42. What about your industry or field excites you?
  43. How does it influence your daily work?
  44. How do you approach personal development and growth outside of your professional responsibilities?
  45. Can you share a book, podcast, or resource that has profoundly influenced your career or personal development and why?

Questions To Ask A Manager In A Coffee Chat

  1. How do you approach leading a team?
  2. What’s your philosophy on management and leadership?
  3. How do you handle conflicts or challenges within the team?
  4. What do you expect from your team members?
  5. How do you support individual growth and development?
  6. What’s the most rewarding part of being a manager?
  7. How do you handle feedback from your team?
  8. How do you stay connected with everyone on the team?
  9. What are some of your team’s current goals and projects?
  10. How do you handle work-life balance for yourself and your team?
  11. What’s the biggest lesson you’ve learned as a manager?
  12. How can I contribute more to the team?
  13. What’s something you wish you had known when you started managing?
  14. How do you encourage creativity and innovation?
  15. How do you define success for your team?
  16. What are some challenges you’re currently facing as a manager?
  17. How do you foster a positive and inclusive team culture?
  18. What are the opportunities for growth and advancement in our team?
  19. How can I best support you as my manager?
  20. How do you identify and nurture potential leaders within the team?
  21. Can you share a management strategy that’s proven particularly effective for you?
  22. How do you approach cross-team collaboration within the organization?
  23. What methods do you use to ensure team members feel their voices are heard?
  24. How do you keep up with the latest management theories or techniques?
  25. What’s your approach to handling underperforming team members?
  26. Can you share a time when you had to lead your team through a significant change or challenge?
  27. How do you foster trust and transparency within the team?
  28. How do you encourage team members to pursue ongoing learning and professional development?
  29. What’s your perspective on remote work and managing a distributed team?
  30. How do you ensure that team goals align with the broader organizational vision?
  31. Can you share how you build a positive onboarding experience for new team members?
  32. What role do you believe a manager should play in conflict resolution?
  33. How do you approach developing a long-term strategic plan for the team?
  34. How do you cultivate a sense of ownership and accountability among team members?
  35. What are your thoughts on flexible working arrangements and how they affect team dynamics?
  36. How do you approach performance reviews?
  37. How do you make them more effective?
  38. Can you share how you maintain a healthy company culture?
  39. What are your strategies for maintaining morale during particularly busy or stressful periods?
  40. How do you ensure that your management style aligns with the values and needs of your team?

Questions To Ask A Hiring Manager In A Coffee Chat

  1. Can you describe the company’s hiring process and what makes it unique or effective?
  2. How does the organization ensure that new hires align with its values and culture?
  3. What are the essential qualities or skills you look for in a candidate for this particular role?
  4. Can you share some common mistakes that candidates make during the application process and how to avoid them?
  5. How does the company support professional growth and career development for its employees?
  6. What’s the onboarding process like?
  7. How does it help new hires integrate into the team?
  8. How do you approach diversity and inclusion in the hiring process, 
  9. What initiatives are in place to support that?
  10. How does the company handle internal promotions? 
  11. What opportunities are there for advancement?
  12. Can you share some success stories of employees who have grown within the organization?
  13. What’s the company’s policy on work-life balance, and how does it support employees in this regard?
  14. How do you ensure that the candidate’s experience and background are a good fit for the team’s needs?
  15. What’s your perspective on remote work, and how has the company adapted to this trend?
  16. How do you handle feedback and communication with candidates throughout the hiring process?
  17. Can you describe the collaboration between different departments when filling a new position?
  18. What role does the team play in the hiring decision, and how are they involved in the process?
  19. How does the company approach continuous learning and training for its employees?
  20. What’s your personal philosophy on talent acquisition, and how do you apply it in your role?
  21. How does the company approach employee retention?
  22. What strategies have been particularly successful?
  23. What are the next steps in the hiring process for this role?
  24. What should candidates expect?
  25. Can you share any insights or tips that could help me or others stand out in the application process?
  26. How do you ensure fairness and objectivity in the hiring process, especially when there are many qualified candidates?
  27. Can you describe a particularly challenging hiring decision you’ve made and what factors influenced it?
  28. What role does employee feedback play in shaping or modifying the hiring process within the company?
  29. How do you stay connected with industry changes and adjust the hiring criteria to match emerging needs or trends?
  30. Can you share an example of how the company has adapted its hiring practices in response to broader economic or social landscape changes?
  31. How do you approach hiring for soft skills, like emotional intelligence or collaboration, in addition to technical abilities?
  32. What initiatives does the company have to support the continuous improvement and development of its hiring processes?
  33. How do the company’s mission and values translate into its employees’ day-to-day experience?
  34. What’s the relationship between the HR department and the individual teams or departments regarding recruiting and hiring?
  35. How do you approach re-hiring former employees or considering candidates who have applied to the company before?

Questions To Ask A CEO Or Senior Leaders In A Coffee Chat

  1. What was the driving force behind you becoming a CEO, and how has that vision evolved?
  2. How do you ensure that the company’s values are consistently reflected across all levels of the organization?
  3. Can you share an unexpected challenge you faced as a CEO and how you navigated it?
  4. How do you approach long-term strategic planning for the company?
  5. What methods do you use to stay connected with employees throughout the organization?
  6. How do you balance the need for innovation with the realities of risk and investment?
  7. Can you describe a decision where you had to weigh the benefits to shareholders against those to employees or customers?
  8. How do you foster a culture of continuous improvement within the organization?
  9. What’s your approach to maintaining work-life balance in such a demanding position?
  10. How do you navigate the complex relationships with the board of directors, investors, and other stakeholders?
  11. What are the essential qualities you look for in your executive team?
  12. How do you nurture those relationships?
  13. How do you stay abreast of industry trends?
  14. How do you determine which ones to pursue or ignore?
  15. Can you share a moment in your tenure as CEO that you found particularly rewarding?
  16. How do you approach corporate social responsibility?
  17. What initiatives are you particularly proud of?
  18. Have you had any significant mentors in your own career?
  19. How do you ensure the company remains agile and adaptable in a rapidly changing business landscape?
  20. What are the most critical metrics or key performance indicators you focus on as a CEO?
  21. How do you approach crisis management?
  22. Can you share an example of how you’ve handled a crisis in the past?
  23. What advice would you give aspiring leaders who want to follow in your footsteps?
  24. How do you envision the future of the company?
  25. What steps are you taking to achieve that vision?
  26. How do you cultivate a sense of unity and purpose among different departments or teams?
  27. Can you describe a time when you had to pivot the company’s direction and how you managed that transition?
  28. What initiatives are you taking to make the company more sustainable or environmentally friendly?
  29. How do you approach building relationships with other industry leaders and competitors?
  30. What’s your philosophy on failure?
  31. How do you encourage a culture where failure is seen as a learning opportunity?
  32. How do you ensure that customer feedback is considered in strategic decisions?
  33. What non-traditional strategies or unconventional wisdom have guided your leadership style?
  34. How do you handle the public relations aspect of being the face of the company?
  35. Can you share an example of a difficult ethical decision you’ve made and how you arrived at your conclusion?
  36. What role does your company play in the broader community or society?
  37. How do you stay grounded and connected to the day-to-day realities of the company’s operations?
  38. What’s your approach to diversity, equity, and inclusion within the organization?
  39. How do you handle the pressure and stress of being at the helm of a major company?
  40. What are your methods for evaluating and adjusting the company’s cultural health?
  41. How do you ensure that the company’s growth is both scalable and sustainable?
  42. What’s your philosophy on corporate philanthropy and giving back to the community?
  43. How do you approach the international aspects of your business, such as global expansion or managing across different cultures?
  44. How do you maintain your personal development and growth while managing the demands of being a CEO?
  45. What’s the legacy you hope to leave behind, and how are you actively working towards it?

Questions To Ask About School

  1. What are you studying in school?
  2. Are there any exams coming up?
  3. How do you handle the balance between school and life?
  4. What are some of your future goals in your education?
  5. Have you had any mentors or influential teachers? How have they impacted you?
  6. What’s the biggest challenge you’ve faced in your studies?
  7. Do you participate in any school clubs or groups?
  8. What’s your favorite part of your daily routine in school?
  9. What do you wish you knew before starting your current studies?
  10. Are there any courses or workshops you’d recommend?
  11. How do you approach continuing education or professional development?
  12. How do you navigate the challenges of online learning?
  13. What do you wish others knew about what you study?
  14. Are there any ethical considerations or dilemmas in your field of study?
  15. How do you approach creativity and innovation in your studies?
  16. If you could go back in time, what would you tell yourself at the beginning of your education?
  17. How do you set and achieve short-term and long-term goals in your studies?
  18. What’s your favorite part about your current major, and why?
  19. How do you balance teamwork with individual responsibilities?
  20. Have you ever had to deal with failure, and how did you overcome it?
  21. How do you stay energized and focused during long study sessions?

Frequently Asked Questions

What is a coffee chat?

A coffee chat is a casual meeting where two people get together over a cup of coffee (or any other beverage) to talk. It’s often used for networking, informal interviews, or just getting to know someone better.

The informal nature of a coffee chat encourages a genuine connection and often leads to a more productive and enjoyable experience. It’s a versatile and accessible way to foster relationships and gain insights into various contexts.

How should I prepare for a coffee chat?

  • Research the person you’re meeting: Knowing a bit about who you’re talking to can make the conversation flow more easily.
  • Have some questions ready: Prepare some questions in advance and follow the conversation wherever it goes.
  • Dress appropriately: A coffee chat is usually informal, but looking neat and put-together is still good.
  • Be on time: Show respect for the other person’s time by arriving when you said you would.

How long should a coffee chat last?

Typically 30 to 60 minutes. A coffee chat should be long enough to have a meaningful conversation but short enough to keep it engaging. If both parties are enjoying the conversation, it might last longer.


Whether you’re chatting with a friend, a manager, or someone you’ve just met, asking the right questions can really stir up a great conversation. It’s all about connecting, learning, and having fun. 

Next time you find yourself in a coffee chat, remember it’s not just about the coffee. It’s about the delightful conversation that happens over it. 

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Robby Salveron

Robby is a multimedia editor at UpJourney with a journalism and communications background.

When she's not working, Robby transforms into an introverted art lover who indulges in her love for sports, learning new things, and sipping her favorite soda. She also enjoys unwinding with feel-good movies, books, and video games. She's also a proud pet parent to her beloved dog, Dustin.