250 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.

Questions About Required Skills And Qualifications

  1. What are the essential skills required for this position?
  2. How important are soft skills like communication and teamwork?
  3. Are there any specific qualifications or certifications needed for this role?
  4. How does the company support skill development and training?
  5. What technical skills are most valuable for this position?
  6. How are new hires assessed for their skills and qualifications?
  7. Are there opportunities for skill enhancement?
  8. What’s the company’s policy on hiring individuals who are self-taught vs. formally educated?
  9. How does the company stay up-to-date with industry standards for qualifications?
  10. How are skills and qualifications balanced with experience when hiring?
  11. What role do project management skills play in this position?
  12. How are employees encouraged to continuously update their skills?
  13. How is applying theoretical knowledge vs. practical skills balanced in this role?
  14. Are there any unique or unconventional skills that are valuable for this position?
  15. How do employees share their skills and knowledge with others in the team?
  16. How are emerging skills or technologies integrated into the role?
  17. What’s the process for recognizing and utilizing transferable skills from other industries?
  18. How are leadership and management skills developed and valued?
  19. How does the company facilitate collaboration between differently skilled team members?
  20. How do you ensure your skills align with the company’s goals and culture?
  21. What’s the importance of cultural fit and alignment with company values?
  22. How are skills and qualifications considered in career advancement?
  23. What’s the approach to continuous learning and adapting to industry changes?
  24. How are employees’ individual talents and strengths identified and utilized?
  25. What’s the company’s perspective on creativity and innovation in this role?
  26. How are problem-solving skills emphasized and developed?
  27. How does the company approach hiring individuals with diverse backgrounds and skill sets?
  28. What tools or assessments are used to evaluate skills during the recruitment process?
  29. How are skills maintained and updated during long-term remote work or virtual collaboration?
  30. What role do negotiation and persuasion skills play in this position?
  31. Are there any platforms or tools provided to help employees self-assess their skills?
  32. How does the company support the development of emotional intelligence and interpersonal skills?
  33. Are there specific expectations for writing or presentation skills in this role?
  34. What’s the company’s approach to adapting the required skills based on customer feedback or needs?
  35. How are analytical and data-driven skills emphasized and developed?
  36. What’s the company’s approach to encouraging lifelong learning and adaptability in skills?
  37. How are ethical considerations and responsibilities integrated into the skillset for this role?
  38. How does the company evaluate the potential and promise in candidates who may lack specific qualifications but show strong aptitude and willingness to learn?

Questions About The Company Culture

  1. Can you describe the overall company culture?
  2. How does the company encourage teamwork and collaboration?
  3. What are the company’s core values?
  4. How does the company support diversity and inclusion?
  5. How would you describe the leadership style here?
  6. What types of social events or team-building activities are common?
  7. How does the company handle conflicts or disagreements?
  8. What’s the company’s approach to innovation and creativity?
  9. How is success celebrated within the team or company?
  10. How does the company give back to the community?
  11. Is there a focus on sustainability or environmental responsibility?
  12. What opportunities are there for continuous learning and development?
  13. How does the company handle feedback from employees?
  14. What’s the company’s policy on work-life balance?
  15. Are there any unique traditions or practices that define the company’s culture?
  16. How does the company support employees’ mental and physical well-being?
  17. How are new ideas and suggestions encouraged?
  18. How does the company maintain its culture during remote work or virtual collaboration?
  19. What role do the company’s mission and vision play in daily work?
  20. How does the company support employees during challenging times?
  21. What’s the process for onboarding new employees?
  22. How is performance evaluated, and how often?
  23. What’s the relationship like between different departments?
  24. How transparent is communication within the company?
  25. How are ethical considerations handled within the company?
  26. How do employees stay connected with each other?
  27. How does the company encourage personal growth?
  28. What’s the attitude towards failure and risk-taking?
  29. How does the company remain competitive in its industry?
  30. How do employees contribute to shaping the company culture?
  31. What role does senior management play in fostering the company culture?
  32. How are customers’ or clients’ values reflected in the company culture?
  33. What role does social responsibility play in shaping the culture here?
  34. How are employees empowered to take ownership and show leadership within the company?
  35. What are some examples of how the company culture has evolved over time?
  36. How does the company ensure its culture aligns with its business strategy?
  37. How is transparency with employees maintained regarding company decisions and changes?
  38. Are there any specific channels for employees to voice cultural concerns or suggestions?
  39. How does the company foster a sense of belonging and community among employees?
  40. What resources are available to employees to understand and engage with the company culture?
  41. How are remote or global team members integrated into the company culture?

Questions About Career Growth

  1. What are the opportunities for career advancement within the company?
  2. How does the company support professional development?
  3. What’s the process for requesting and receiving promotions or raises?
  4. Are there any mentorship or coaching programs available?
  5. What’s the typical career path for someone in this role?
  6. How are employees encouraged to set and pursue career goals?
  7. How does the company invest in training and education?
  8. How does the company handle internal job transfers or role changes?
  9. Are there any resources available for employees wanting to further their education or skills?
  10. How often are performance reviews conducted, and what do they entail?
  11. How are high-performing employees recognized and rewarded?
  12. How does the company support long-term career planning?
  13. What opportunities are there for working on special projects or initiatives?
  14. How do employees keep up with industry trends and changes for career growth?
  15. How does the company encourage innovation and creativity in career development?
  16. Are there any international opportunities or assignments?
  17. How does the company ensure career growth aligns with personal values and interests?
  18. What’s the company’s retention rate?
  19. How does it support employee retention?
  20. How does the company handle career transitions, such as retirement or shifting roles?
  21. How is feedback on career development provided?
  22. How does the company support work-life balance as employees advance in their careers?
  23. What’s the relationship between managers and team members in terms of career development?
  24. Are there any unique challenges or opportunities for career growth within the company?
  25. How does the company’s growth strategy impact individual career opportunities?
  26. What skills are considered most valuable for career advancement?
  27. How are employees supported in building a network within the industry?
  28. What’s the company’s perspective on lateral moves or taking on different roles to grow professionally?
  29. How does the company identify and nurture potential future leaders?
  30. What’s the approach towards encouraging employees to pursue passions and interests within their career path?
  31. How are managers trained to support the career growth of their team members?
  32. Are there any partnerships with educational institutions or organizations to support employee growth?
  33. What is the company’s success rate of employees reaching their desired career growth milestones?
  34. How does the company support employees needing to relocate for career advancement?

Questions About The Daily Routine

  1. What does a typical day look like in this role?
  2. How do you start your workday?
  3. What are the main tasks you perform each day?
  4. How much time is spent on meetings versus individual work?
  5. How do you prioritize your daily tasks?
  6. Is there flexibility in the daily schedule?
  7. What’s the most challenging part of your daily routine?
  8. How do you usually end your workday?
  9. Do you often work overtime?
  10. How do you handle unexpected tasks or challenges during the day?
  11. Is there a specific dress code for the office?
  12. How do you usually spend your lunch break?
  13. What’s the most enjoyable part of your daily routine?
  14. Are there any daily rituals or practices that are important to the team?
  15. How do you interact with other team members during the day?
  16. Do you collaborate with other departments?
  17. How is the workflow managed throughout the day?
  18. What’s the process for handling urgent or last-minute tasks?
  19. How do you keep up with emails and communication throughout the day?
  20. Is working from home or remote work arrangement an option?
  21. How often do you interact with clients or customers?
  22. Are there any specific daily goals or targets?
  23. How is feedback on daily work provided?
  24. How does the team handle stressful days or tight deadlines?
  25. What’s the balance between creativity and routine tasks?
  26. How do you stay organized and manage your time?
  27. How do you keep up with industry changes in your daily work?
  28. Are there any specific resources or support available for everyday tasks?
  29. How do you maintain a work-life balance with your daily routine?
  30. What’s the process for tracking progress on daily tasks and projects?
  31. How do you handle interruptions or distractions during the workday?
  32. What’s the approach to multitasking, and how is it managed?
  33. Are there specific safety protocols or guidelines followed daily?

Questions About Teamwork And Collaboration

  1. How are teams structured within the company?
  2. What is the typical team size?
  3. What strategies are used to promote effective collaboration among team members?
  4. How are cross-functional teams formed and managed?
  5. What role does leadership play in fostering teamwork?
  6. How does the team stay aligned with company values and goals?
  7. How are individual strengths and weaknesses balanced within a team?
  8. How are team successes celebrated, and how are challenges addressed?
  9. How does the company ensure all team members have an equal voice and representation?
  10. How are new team members onboarded and integrated into the existing team structure?
  11. How does the team collaborate with other departments or external partners?
  12. What are the expectations regarding collaboration on projects outside of regular work hours?
  13. How are team responsibilities and roles defined and communicated?
  14. What’s the company’s approach to collaborative decision-making?
  15. How does the team handle feedback and continuous improvement?
  16. What’s the approach to project management within the team?
  17. How are the team’s goals set, monitored, and achieved?
  18. What are the common challenges in teamwork, and how are they overcome?
  19. How does the company promote a positive and supportive team culture?
  20. How does the team adapt to sudden changes or shifts in project direction?
  21. Are there opportunities for team members to mentor or coach each other?
  22. What is the company’s policy on transparency and openness within the team?
  23. How are team members held accountable for their roles and responsibilities?
  24. What is the role of empathy and understanding in building a strong team?
  25. Are there any formal processes for peer review or collaboration quality control?

Questions About Challenges And How They Are Addressed

  1. What are the most common challenges faced in this role?
  2. How does the company support employees in overcoming challenges?
  3. What’s the approach to handling mistakes or failures?
  4. How are conflicts between team members resolved?
  5. Are there any specific protocols for handling urgent or crisis situations?
  6. How are challenges with clients or customers managed?
  7. What’s the company’s policy on seeking external help or consultation for complex challenges?
  8. How are challenges communicated and addressed across different departments?
  9. How does the company ensure that challenges don’t affect employee well-being?
  10. What resources are available for employees who are facing difficulties in their tasks?
  11. How does the team collaborate to overcome challenges?
  12. How are challenges with technology or tools handled?
  13. What’s the approach to managing ethical dilemmas or challenges?
  14. How are challenges related to diversity and inclusion addressed?
  15. How does the company handle competition and challenges in the market?
  16. What’s the strategy for managing challenges during rapid growth or change?
  17. How are personal or career-related challenges addressed and supported?
  18. How does the company encourage a proactive approach to identifying and addressing challenges?
  19. What’s the process for employees to voice concerns or difficulties?
  20. How are lessons learned from challenges documented and shared?
  21. What role do managers play in supporting their team through challenges?
  22. How does the company balance business needs with employee needs during challenging times?
  23. What’s the company’s approach to legal or regulatory challenges?
  24. What’s the company’s philosophy on risk-taking and managing potential challenges?
  25. How are challenges related to sustainability or environmental responsibility managed?
  26. What role does innovation play in overcoming challenges and driving continuous improvement?

Questions About The Industry And Market Trends

  1. How does the company stay up-to-date with the latest industry trends and insights?
  2. What role does market research play in the company’s strategy and decision-making?
  3. How does the company differentiate itself from competitors in the industry?
  4. Are there any emerging technologies or methodologies shaping the industry?
  5. How does the company adapt to regulatory changes or legal considerations in the market?
  6. How does the company anticipate and respond to customer needs and preferences?
  7. What are the main challenges and opportunities facing the industry right now?
  8. How are employees educated about industry trends and market dynamics?
  9. What’s the company’s approach to sustainability and environmental considerations within the industry?
  10. How does the company engage with industry events, conferences, or forums?
  11. What’s the company’s perspective on innovation and disruption within the industry?
  12. How does the company leverage data and analytics to understand market trends?
  13. What key performance indicators does the company track in line with industry standards?
  14. How does the company handle economic fluctuations and market uncertainties?
  15. What’s the company’s approach to global market trends and international expansion?
  16. How does the company identify new market opportunities or niches?
  17. How are industry trends integrated into product development or service offerings?
  18. What role do government policies and regulations play in the industry?
  19. What’s the long-term vision of the company in line with industry evolution?
  20. How does the company collaborate with academia or research institutions within the industry?
  21. What are the key demographics or customer segments the company focuses on within the market?
  22. What are the social and cultural factors that influence the industry and the company’s approach?
  23. How does the company contribute to thought leadership within the industry?
  24. What are the anticipated future trends in the industry
  25. How is the company preparing for them?
  26. How does the company ensure quality and compliance with industry standards and best practices?

Questions About The Tools and Technology Used

  1. What tools or software do you use regularly?
  2. Are there any in-house developed tools or proprietary technologies?
  3. How are employees trained to use new tools or technologies?
  4. What’s the approach to managing data security and privacy within the tools used?
  5. How are technological choices aligned with the company’s business goals and values?
  6. How does the company encourage innovation and experimentation with new tools?
  7. What role do open-source tools or platforms play within the company’s technology stack?
  8. How are the effectiveness and efficiency of tools and technology evaluated?
  9. How are tools and technologies customized to fit specific project needs?
  10. What’s the process for tech support or troubleshooting tool-related issues?
  11. How are employees involved in the decision-making process for adopting new tools or technologies?
  12. What’s the company’s approach to integrating different tools for seamless workflow?
  13. How does the company stay compliant with legal regulations related to technology use?
  14. Are there any collaborations with technology vendors or developers?
  15. How are technology needs balanced with budget considerations?
  16. What’s the approach to technology during remote work or virtual collaboration?
  17. How are technology choices influenced by customer needs or industry standards?
  18. How does the company promote accessibility and usability in the tools used?
  19. What’s the process for ongoing monitoring and maintenance of tools and technologies?
  20. What role does sustainability play in the choice and utilization of technology?
  21. How can emerging technologies like AI or blockchain be integrated into the company’s workflow?
  22. What’s the company’s approach to continuous learning and adaptation to technology?
  23. How are tools and technologies documented and knowledge shared across the team?
  24. How does the company approach legacy tools and migration to newer technologies?
  25. How do tools and technologies support the company’s commitment to quality and excellence?
  26. How does the company evaluate the success or failure of a newly implemented technology?
  27. How does the company approach the integration of legacy systems with newer technologies?

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 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.