265 Questions to Ask When Seeking Career Advice

When we’re on the road to building our dream career, we often find ourselves standing at crossroads, unsure of which way to go. That’s where career advice comes in handy! 

Whether you’re just starting out, switching industries, or aiming for the top job, knowing what to ask can help you make the right choices. So, let’s dive into some important questions that can give you that extra edge in your career journey.

Questions To Ask When Choosing A Career

  1. What made you choose this career?
  2. What skills or talents are most critical to success in this job?
  3. What are the biggest challenges of this job?
  4. Can you describe a typical day or week in this career?
  5. What do you enjoy most about your work?
  6. Is there anything you dislike about your job?
  7. What kind of education or training is needed for this job?
  8. How did you get started in this career?
  9. How can I get my foot in the door in this industry?
  10. What’s the usual career path for someone in this field?
  11. What’s the work-life balance like in this job?
  12. What’s the best way to network in this industry?
  13. How secure is a career in this field?
  14. What kind of money can I expect to earn at the start and as I progress?
  15. How much demand is there for this job in the future?
  16. What are the important “soft skills” needed in this job?
  17. What opportunities for growth exist in this field?
  18. Is there anything you wish you had known before you started this career?
  19. Can you suggest any resources (books, websites, organizations, etc.) to learn more about this field?
  20. What advice would you give to someone just starting out in this career?
  21. How does this job contribute to society or the community?
  22. What kind of person thrives in this industry?
  23. Are there different specialties within this field? What are they?
  24. How has this job or industry changed in the last few years?
  25. What are some misconceptions people have about this job?
  26. How often do you work outside of your regular business hours?
  27. What personal qualities or characteristics are essential for someone in this job?
  28. Is ongoing learning or training a part of this job? If so, how?
  29. How would you describe the culture in this job or industry?
  30. What are some things I can do now to prepare for this career?
  31. How would you rate job satisfaction in this career on a scale of 1 to 10?
  32. What sets someone apart from others in this field?
  33. What is the most rewarding part of your job?
  34. What’s the future of this industry according to current trends?
  35. Are there any specific certifications or credentials that can help in this career?

Questions To Ask When Seeking Career Advice For Career Progression

  1. What steps should I take to advance in my career?
  2. Can you recommend any specific training or courses that would help me progress?
  3. How important is networking for advancement in this field?
  4. What kind of performance metrics are essential for advancement in my role?
  5. How can I develop my leadership skills for future advancement?
  6. What are some common roadblocks to progression in this career, and how can I overcome them?
  7. Are there any specific projects or roles that could help me stand out for promotion?
  8. Can you share an example of someone who advanced quickly in this field? What did they do?
  9. How can I show my commitment to this role and company?
  10. Should I consider a mentor or coach to assist with my career progression?
  11. What skills are most in-demand in higher-level roles in this industry?
  12. How can I better communicate my career aspirations to management?
  13. What additional responsibilities can I take to show I’m ready for advancement?
  14. How do you recommend handling a situation where my advancement has been slow?
  15. Should I consider lateral moves (moving to a different team or role at the same level) for eventual career progression?
  16. How can I ask for feedback to improve my performance and chances of progression?
  17. Can you recommend any books or resources that focus on career growth?
  18. How can I stay motivated when progression is slow?
  19. Is it better to focus on depth (becoming a specialist) or breadth (becoming a generalist) of knowledge in my field for advancement?
  20. How can I improve my personal brand to aid in my career advancement?
  21. What are the qualities that the senior management values most when considering promotions?
  22. How can I effectively negotiate for a promotion or raise?
  23. Should I consider further education, like a Master’s degree or a Ph.D., for career progression?
  24. Can you give me an example of a career move you consider smart?
  25. What potential career pitfalls should I be aware of in this industry?
  26. How can I make my achievements more visible to my superiors?
  27. How should I handle job transitions (like job changes within the same industry)?
  28. Are there specific industry events or conferences I should attend for networking and professional growth?
  29. How do you know when it’s the right time to move on to a new job or company?
  30. How important is the role of mentors and sponsors in career advancement?
  31. How can I ensure my skills and knowledge stay current as my industry evolves?
  32. What would you suggest for someone who feels stuck in their current position?
  33. Should I consider roles in different industries to broaden my experiences?
  34. How can I develop resilience in my career journey?
  35. What strategies can I use to handle a career plateau?
  36. How do I keep track of my accomplishments and use them to showcase my capabilities?

Questions To Ask When Seeking Career Advice From Senior Leaders

  1. How did you rise to your current position?
  2. Can you share some of the challenges you faced on your career journey?
  3. What do you think are the most crucial skills for a leader in this industry?
  4. How do you handle difficult decisions?
  5. What’s your approach to mentoring and developing team members?
  6. What’s the best piece of career advice you’ve ever received?
  7. How do you manage work-life balance in a leadership role?
  8. Can you share a time when you made a mistake as a leader and how you handled it?
  9. What are your strategies for managing stress and pressure?
  10. How do you keep your team motivated, especially during challenging times?
  11. What are the top qualities you look for when promoting someone to a leadership position?
  12. How important is company culture in your organization, and how do you contribute to it?
  13. Can you share an example of a significant problem you solved in your role?
  14. How do you encourage creative thinking within your team?
  15. What’s your approach to dealing with conflict within the team?
  16. How do you set goals for your team and track progress?
  17. What do you wish you knew before you took on your first leadership role?
  18. How do you build strong relationships with your team and colleagues?
  19. What advice do you have for someone looking to step into a leadership role for the first time?
  20. What’s the most rewarding aspect of being a leader in this industry?
  21. What’s the biggest risk you’ve taken in your career, and how did it turn out?
  22. How do you continue to learn and grow in your leadership role?
  23. How do you handle feedback and criticism?
  24. Can you share an accomplishment you’re particularly proud of in your career?
  25. How have you adapted your leadership style to meet the needs of a changing workforce or industry?
  26. How do you ensure your decisions align with the company’s vision and values?
  27. How do you manage disagreements with higher management or with your own team?
  28. How do you foster diversity and inclusion in the workplace?
  29. How do you approach corporate social responsibility in your leadership role?
  30. What kind of legacy do you hope to leave in your current position or in this industry?
  31. How do you prioritize your tasks and responsibilities?
  32. Can you share a resource (book, course, mentor, etc.) that significantly shaped your leadership style?
  33. How do you define success in your role?
  34. How do you keep up-to-date with industry changes and developments?
  35. What steps do you take to ensure you make well-informed decisions?
  36. How do you deal with failure or setbacks?
  37. What role does emotional intelligence play in your leadership style?
  38. What’s one question you wish people would ask about your job or industry?

Questions To Ask When Seeking Career Advice After A Job Loss

  1. How can I remain positive and motivated during a job search after losing my job?
  2. What resources are available to help me after a job loss?
  3. How should I explain my job loss in an interview?
  4. What are the best strategies to network and find new opportunities after a job loss?
  5. Should I consider a career change after losing a job?
  6. How can I use this time to reevaluate my career goals?
  7. What steps can I take to manage financial stress during this period?
  8. How should I approach updating my resume and LinkedIn profile now?
  9. How can I maintain a routine or structure in my day-to-day life during this transition period?
  10. Should I consider temporary or contract work while looking for a new full-time position?
  11. How can I handle feelings of rejection or failure after a job loss?
  12. Is this a good time to pursue further education or professional training?
  13. Should I consider starting my own business or becoming a freelancer?
  14. How can I address any skill gaps that might be holding me back?
  15. How can I take care of my mental health while dealing with job loss?
  16. Should I consider seeking help from a career counselor or coach?
  17. How do I evaluate potential new employers’ job security and stability?
  18. How can I leverage my previous work experience in my job search?
  19. Should I consider industries or roles I haven’t previously worked in?
  20. How can I use this experience as a growth opportunity?
  21. How long should I expect my job search to take after losing a job?
  22. How do I keep up with industry trends and maintain relevant skills during this period?
  23. How can I improve my interview skills to increase my chances of getting a new job?
  24. What are the best ways to ask for references or recommendations after a job loss?
  25. How can I use this time to create a strong personal brand?
  26. Should I consider working with a recruitment agency?
  27. How can I practice resilience during this challenging time?
  28. What is the best way to negotiate salary and benefits when I land a new job?
  29. Should I consider relocating for new job opportunities?
  30. How can I ensure my next job aligns with my long-term career goals?
  31. How do I maintain good relationships with my former colleagues and employers?
  32. Should I consider internships or apprenticeships as a way to re-enter the job market?
  33. How do I stay motivated if the job search takes longer than expected?

Questions To Ask When Seeking Career Advice For Switching Industries

  1. How can I identify transferable skills relevant to the new industry?
  2. What steps should I take to understand the culture of the new industry?
  3. How can I network effectively within the new industry?
  4. What are the key differences in job roles between my current and target industry?
  5. How can I tailor my CV and cover letter to fit the new industry?
  6. Should I consider additional training or certifications for the new industry?
  7. How can I effectively communicate my interest in the new industry during interviews?
  8. How should I manage potential salary changes when switching industries?
  9. What are the potential challenges I could face in the new industry?
  10. How long should I anticipate the job search to take when changing industries?
  11. What strategies can help me keep up with new trends and developments in the target industry?
  12. Should I consider an internship or entry-level position to gain experience in the new industry?
  13. How can I use my previous industry experience as a strength in the new industry?
  14. How should I address questions about my industry switch from potential employers?
  15. How important is it to know the industry jargon or specific language of the new industry?
  16. What are the growth and stability prospects in the new industry?
  17. How can I get a mentor who is already in the industry I want to move into?
  18. How can I stay resilient during the transition period?
  19. How can I evaluate if the industry switch is a good fit for me once I’ve made the move?
  20. How can I build credibility in my new role within a different industry?
  21. Should I consider seeking the help of a career coach specializing in industry transition?
  22. How can I gain practical experience in the new industry before officially transitioning?
  23. What steps should I take to understand the competitive landscape of the new industry?
  24. How can I demonstrate my commitment and passion for the new industry?
  25. How should I manage relationships with colleagues and peers during this transition?

Questions To Ask When Seeking Career Advice For Balancing Work-Life

  1. How can I set healthy boundaries between my work and personal life?
  2. How should I manage stress to avoid burnout?
  3. What strategies can help me to increase productivity during work hours?
  4. How can I discuss flexible working arrangements with my employer?
  5. How should I balance work responsibilities with personal or family commitments?
  6. What hobbies or activities might help me to unwind and disconnect from work?
  7. How can I maintain good physical health while managing a busy work schedule?
  8. How should I handle working from home while also managing household responsibilities?
  9. How important is it to take regular breaks during the workday?
  10. How can I manage feelings of guilt when taking time off for personal reasons?
  11. What strategies can help me prioritize tasks effectively to ensure work-life balance?
  12. How should I handle work-related communication during non-working hours?
  13. How can I incorporate exercise and healthy eating into a busy workday?
  14. How can I ensure I’m getting enough sleep when working long hours?
  15. What techniques can I use to manage work anxiety and maintain mental health?
  16. How can I leverage technology to improve work-life balance?
  17. How can I maintain strong relationships with family and friends while working full-time?
  18. How can I effectively handle work during periods of personal crisis or difficulty?
  19. How can I ensure I spend quality time with loved ones despite a demanding job?
  20. Should I consider a job with a shorter commute to improve my work-life balance?
  21. What are some ways to create a conducive work environment at home?
  22. How can I handle work pressure without it affecting my personal life?
  23. Should I consider a job with a more flexible schedule to achieve a better work-life balance?
  24. How can I ensure I’m not overworking when my work and home environments are the same?
  25. How important is taking vacations in maintaining a work-life balance?
  26. What are some ways to stay connected with my team while working remotely?
  27. How can I create a daily routine that supports both my work and personal life?
  28. Should I consider job roles that allow for more autonomous work to improve work-life balance?

Questions To Ask When Seeking Career Advice For Students

  1. What are some things I should consider when choosing a major?
  2. How do I know if a certain career path is right for me?
  3. What types of internships will help me in this career path?
  4. How can I make the most of my time in college to prepare for this career?
  5. What skills can I develop now that would be beneficial in this field?
  6. What are some common entry-level jobs in this industry?
  7. How important are grades when finding a job in this field?
  8. What kinds of extracurricular activities would you recommend?
  9. How can I start networking while I’m still in school?
  10. What should I look for in a mentor?
  11. Should I consider studying abroad?
  12. What kinds of research projects could help me stand out to future employers?
  13. How do I create an effective resume with limited work experience?
  14. What are some tips for handling job interviews in this industry?
  15. What qualities or experiences are employers in this field looking for in new graduates?
  16. How useful are job fairs and campus recruitment events?
  17. Should I consider attending graduate school right after my bachelor’s degree, or should I gain work experience first?
  18. How can I use social media platforms, like LinkedIn, to boost my career prospects?
  19. What are common mistakes students make when starting their careers, and how can I avoid them?
  20. How can I convert an internship into a full-time job?
  21. What are some effective strategies for job hunting while still in school?
  22. How can I manage stress as I transition from college to a career?
  23. Should I consider part-time jobs relevant to my field during my studies?
  24. How can I effectively articulate my career goals in a job application?
  25. How do I establish a professional reputation while I’m still in school?
  26. How can I gain practical experience in my field while I’m still studying?
  27. Should I consider working for a startup or a well-established company after graduation?
  28. What are some ways to handle rejection or setbacks in job applications?
  29. How do I decide between multiple job offers or opportunities?
  30. How can I apply the knowledge from my studies to real-world scenarios?
  31. How important is volunteering in my field of interest?
  32. How do I balance the need to earn money right after graduation with the desire to wait for a job that fits my career goals?
  33. How should I approach references—who should I ask, and how?
  34. What steps can I take to continue learning and developing professionally after graduation?
  35. How can I stay motivated during a difficult job search?
  36. What’s the best way to keep up with industry trends and advancements?
  37. What should I prioritize in my first job—salary, benefits, learning opportunities, company culture, or something else?
  38. How can I demonstrate transferable skills in a job interview?
  39. How should I navigate the first few months on the job to set a strong foundation for my career?
  40. How can I handle a situation where my career interests change while in school?
  41. How can I build professional relationships with my professors and lecturers?
  42. What resources are available on campus to help me prepare for my career?
  43. What are some practical ways to handle student loan debt while pursuing my career?
  44. How important is the reputation of my university or course when it comes to job applications?
  45. How can I demonstrate leadership skills on my resume or in a job interview?
  46. What are some good strategies for time management while juggling studies, internships, and job applications?
  47. Should I consider entrepreneurship as an option after graduation?
  48. How can I stay resilient and motivated during challenging periods in my academic and professional journey?
  49. How should I address gaps in my resume, such as a semester off, for personal reasons?
  50. What’s the best way to negotiate my first salary?
  51. Should I consider careers or jobs that aren’t directly related to my degree?
  52. How important is having a career plan, and how flexible should I be with it?
  53. What should I know about workplace ethics before starting my first job?
  54. How can I make a positive first impression at my new job?
  55. How can I handle workplace conflicts professionally?
  56. How can I develop a lifelong learning mindset to stay relevant in my career?
  57. What should I do if I feel unsure or overwhelmed about my career choices?
  58. What factors should I consider when deciding whether to relocate for a job?
  59. How do I evaluate a company’s culture when considering job opportunities?
  60. How can I develop confidence and assertiveness in professional situations?
  61. How can I stay mentally healthy during the job-hunting process?
  62. What strategies can help me deal with the uncertainty of today’s job market?
  63. How can I navigate office politics as a new professional?
  64. How can I stand out in a competitive job market?
  65. How important is understanding corporate hierarchy in my first job?
  66. What are some effective ways to manage workplace stress?
  67. How can I turn a short-term or contractual job into a permanent position?
  68. How can I manage my finances effectively early in my career?
  69. How can I gain confidence in public speaking or presentations?
  70. How do I continue developing my skills once I have secured a job in my field?

Frequently Asked Questions

When should I seek career advice?

You can seek career advice anytime. Some good times could be:

When you’re unsure: If you don’t know what job you want or if you want to change your career.

Before big steps: Like before choosing a course in school or accepting a job offer.

When you feel stuck: If you’re in a job but are unhappy or making progress.

How often should I seek career advice?

Determining how often to seek career advice varies based on personal circumstances and career progression. 

For some, an annual check-in with a career advisor or mentor might suffice. This yearly consultation provides an opportunity to reflect on your career path, establish goals for the future, and address potential challenges, keeping you on a steady growth trajectory.

However, during major transitions such as considering a significant career change, diving into a new industry, or significant advancements in your field, you may find more frequent consultations helpful. 

Regular discussions with a career advisor during these times can provide invaluable guidance, reassurance, and assistance in navigating uncertainties, ensuring that you stay adaptable and current in your profession.

What if I ask a question and I don’t understand the answer?

If you ask a question and don’t understand the answer, don’t hesitate to ask for clarification. You could paraphrase their response back to them to confirm your understanding. 

Alternatively, you can request them to simplify their explanation or provide an example for better clarity. If it’s a complex topic, ask them to recommend additional resources for you to explore and gain a deeper understanding.

“Could you explain that a bit more?”
– “I’m not sure I understand. Could you possibly put it in simpler terms?”
– “Could you provide an example to illustrate your point?”
– “So, what I’m hearing is… Is that correct?”
– “That’s a bit complex for me. Could you break down that concept into smaller parts for me?”
“I’m not familiar with that term. Could you define it for me?”

What should I do if I get conflicting advice when asking these questions?

Receiving conflicting advice when seeking career guidance is common due to varying experiences and perspectives. In such situations, weigh each piece of advice against your career goals and personal values

Also, consider the source of the advice: their understanding of your aspirations and their experience in your field can influence its relevance. 

If conflicted, don’t hesitate to seek more opinions. Use these insights as input but trust your judgment to make the final decision that aligns with your career path.

Are there other resources I should look at besides asking these questions?

Yes, there are many other resources for career advice. These could include:
– Books
– Online resources
– Career counselors
– Job fairs

It’s a good idea to use many sources of information when making career decisions.


Choosing a career or making a change in your professional life doesn’t have to be like finding a needle in a haystack. With the right questions, you can unlock doors to opportunities and insights that align with your goals and passions. 

So, the next time you find yourself pondering your career, remember that asking the right questions isn’t just about getting answers; it’s about shaping your future. Happy career 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.