150 Questions to Ask When Job Shadowing

Ever wondered what it’s like to walk in someone else’s work shoes for a day? That’s what job shadowing is all about! It’s a chance to follow a professional around and see what they do, up close and personal. It’s like a behind-the-scenes tour of a career you might be curious about. 

It’s exciting, but where do you start? What do you ask? Having the right questions at your fingertips can turn a regular visit into an eye-opening experience. 

Whether you’re exploring a new career or just curious about what someone does all day, here’s your guide to making your job shadowing a real adventure.

Understanding the Role

  1. What does a typical day look like for someone in this position?
  2. Can you walk me through your daily tasks and responsibilities?
  3. How do you prioritize your work?
  4. What are the core skills required for this job?
  5. How do you measure success in this role?
  6. What projects are you currently working on?
  7. Can you describe an instance where you had to overcome a significant challenge in this role?
  8. How does this position contribute to the overall goals of the department/company?
  9. What tools and technology do you use daily?
  10. How collaborative is this role within the team and with other departments?
  11. What types of decisions do you make, and what information do you use?
  12. How has this role evolved over time?
  13. What did you wish you knew before you started this job?
  14. How do you stay updated with industry trends and challenges?
  15. What is your favorite part about your job?
  16. What routine maintenance or administrative tasks are involved?
  17. How do you handle unexpected situations or emergencies?
  18. Can you show me an example of a project you’ve completed?
  19. How do you balance hands-on tasks with strategic planning?
  20. What kind of feedback or performance reviews do you receive?
  21. How much autonomy do you have in this role?
  22. Who do you report to, and what is that relationship like?
  23. What are the less-known aspects of this job?
  24. Are there opportunities to specialize within this role?
  25. How do you see this role changing in the next few years?

Industry-Specific Practices

  1. What regulations or compliance issues directly affect your job?
  2. How do industry trends impact your daily work?
  3. What is the biggest challenge your industry is facing right now?
  4. In what ways is technology changing your profession?
  5. How do you ensure quality and excellence in your work?
  6. Can you describe a recent industry development and how it has affected your role?
  7. What are the most critical industry-specific skills in this field?
  8. How does your role differ from similar positions in other industries?
  9. What trade publications, websites, or professional associations do you recommend following?
  10. How does the competitive landscape affect your job?
  11. Can you discuss an industry-standard process and how it is applied here?
  12. Are there ethical concerns that are unique to this industry?
  13. What industry-specific training or certifications are most beneficial?
  14. How does the global market influence your industry and your role?
  15. How do you keep abreast of changes in industry regulations?
  16. What kind of industry networking events or conferences do you find most valuable?
  17. Are there any misconceptions people have about this industry?
  18. How does the local economy impact the industry and your job?
  19. In what ways do customer preferences shape your work?
  20. How do you anticipate the industry will evolve in the next 5 years?
  21. What industry challenges have you faced, and how did you tackle them?
  22. What are common career progression routes within this industry?
  23. How do finance and budget considerations affect decision-making in your role?
  24. How does your company innovate within the industry?
  25. Can you show me a best-practice example that’s industry-specific to your role?

Company Culture and Dynamics

  1. How would you describe the company culture here?
  2. What values does the company prioritize for its employees and clients?
  3. How does management support the development of its employees?
  4. What are some team traditions or events that the company hosts?
  5. Can you tell me about the organizational structure and how the teams interact?
  6. How are achievements recognized and rewarded within the company?
  7. Could you tell me about one of the company’s recent successes?
  8. How does diversity and inclusion play a role in the company culture?
  9. What kind of work-life balance initiatives does the company have in place?
  10. How does the company handle conflicts or disagreements?
  11. Are there opportunities for cross-departmental collaboration?
  12. How is feedback given and received across the company?
  13. What is the company’s approach to innovation and new ideas?
  14. Can you describe the leadership style within the organization?
  15. How does the company support continuous learning and professional development?
  16. What social or community services is the company involved with?
  17. How transparent is the company regarding its goals and operations?
  18. Can you discuss how decisions are made and communicated?
  19. In what ways does the company support the well-being of its employees?
  20. How does the company address changes in the marketplace?
  21. How does the company support teamwork and cohesiveness?
  22. What’s the onboarding process like for new employees?
  23. Can you describe a significant change the company has undergone and how it was managed?
  24. How does the company foster creativity and encourage innovation?
  25. What do you enjoy most about the company culture?

Career Path and Development

  1. What does the typical career progression look like in this field?
  2. How do you see this role leading to other opportunities in the company?
  3. Are there mentoring or coaching programs available?
  4. What professional development opportunities does the company offer?
  5. What skills and experiences help someone advance in this career?
  6. How does the company support career growth and mobility?
  7. Can you share your own career path and how you got to where you are today?
  8. What are the potential next steps after this job?
  9. What kinds of achievements or milestones are necessary for progression?
  10. How often do performance reviews occur, and what do they entail?
  11. Are there opportunities for further education or training?
  12. What types of roles do people move into after holding this position?
  13. How is individual initiative viewed within the company?
  14. What qualities does the company look for when promoting someone?
  15. How does one transition into a leadership role within this organization?
  16. Can you discuss how tenure impacts career advancement?
  17. How do you keep your skills relevant to meet career advancement criteria?
  18. What challenges have you faced while climbing the career ladder?
  19. Are there new roles or positions being created as the company grows?
  20. How does company performance affect individual career opportunities?
  21. What advice do you have for someone looking to advance in this field?
  22. How approachable is leadership in discussing career paths?
  23. What resources are available for personal and professional growth?
  24. How does the company identify and nurture high-potential employees?
  25. What kind of support is offered for lateral moves within different departments?

Daily Challenges and Rewards

  1. What are some of the most rewarding aspects of this job?
  2. What are the most common challenges you face in this position?
  3. How do you manage stress or high-pressure situations?
  4. Can you give an example of a particularly successful moment in your job?
  5. How do you stay motivated during repetitive or routine tasks?
  6. What keeps you energized and engaged in your work?
  7. How do you balance short-term demands with long-term goals?
  8. What processes do you have in place to handle tight deadlines?
  9. Can you share a time when you had to adapt quickly to changes?
  10. How do you ensure excellence while managing several tasks?
  11. What is your approach to innovation and problem-solving?
  12. How do you maintain a positive work environment, even during difficult times?
  13. How have your responsibilities expanded or changed recently?
  14. What has been your biggest learning curve in this role?
  15. How do you measure personal success in your daily work?
  16. Can you describe a project where you had to juggle multiple responsibilities?
  17. How do you contribute to team success while managing individual tasks?
  18. How do you handle feedback, both positive and constructive?
  19. Can you describe a situation where you went above and beyond what was expected?
  20. What strategies do you use for effective time management?
  21. How has the company supported you through a work challenge?
  22. What tools or resources do you recommend for managing daily tasks?
  23. How do you prioritize client needs and satisfaction?
  24. Can you share an example of how you solved a work-related problem?
  25. How do you stay focused and productive in a fast-paced environment?

Skills and Education

  1. What specific skills are essential for success in this role?
  2. How did your education prepare you for this job?
  3. Are there any additional certifications or training that have been particularly beneficial?
  4. Which soft skills do you find most useful on a day-to-day basis?
  5. How do you continue to learn and develop your professional skills?
  6. What opportunities exist for learning new skills within the company?
  7. How important is formal education in advancing in this field?
  8. Can you recommend any online courses or resources to enhance industry knowledge?
  9. How does the company support ongoing education for its employees?
  10. What technical skills are in high demand in your role?
  11. How do you apply your past experiences to your current job?
  12. How does the company keep up with the latest skill requirements for the industry?
  13. What unconventional skills have proven surprisingly helpful?
  14. How do you adapt to new tools or technologies introduced in the workplace?
  15. What advice would you give to someone looking to develop their skills?
  16. Are there specific skills you’re looking to develop in the near future?
  17. How do you mentor or help others grow their skills?
  18. What collaboration skills are necessary for this job?
  19. How does your educational background influence your perspective on the work?
  20. How has the skillset required for this role changed over time?
  21. What kind of on-the-job training can a newcomer expect?
  22. How do you balance technical expertise with creative thinking?
  23. What skills do you think will be necessary for this role in the future?
  24. How do you keep up with professional certifications and requirements?
  25. What impact has continued learning had on your career progression?

Frequently Asked Questions

Why should I consider job shadowing?

Job shadowing offers many benefits:

Learning: You’ll gain firsthand experience in a profession.
– Networking: It helps in making connections in your desired field.
– Clarification: You’ll see if this career is the right fit for you.

What should I wear and bring to a job shadowing day?

When job shadowing, it’s good to dress professionally, like how employees in that field dress. Bring a notebook and pen to take notes, and have a list of questions ready. It’s also polite to bring a copy of your resume in case it comes up in conversation.

How do I arrange a job shadowing opportunity?

Arranging a job shadowing opportunity involves a few steps:

Research: Find companies and professionals in your area of interest.
Contact: Reach out via email or phone, explaining why you’re interested.
Follow-up: Send a polite follow-up to show your genuine interest if needed.
– Prepare: Once confirmed, prepare by researching the company and coming up with questions.

How long does a typical job shadowing experience last?

Job shadowing can vary in length. It might be as short as a few hours or as long as a week

Usually, it depends on the professional’s availability and what you hope to learn. It’s best to discuss the timing with the person you’re shadowing to find a schedule that works for both of you.


Job shadowing can be a real eye-opener, giving you a glimpse of your future. By asking the right questions, you’ve not only gained insights but also built connections that could open doors down the road. 

So next time you shadow someone, go ahead, and ask away! The answers might just inspire your next big career move. Happy exploring!

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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.