questions to ask your mentor

31 Questions To Ask A Mentor When Working Toward The Next Step in Your Career

Table of Contents

Let’s face it… most of us just aren’t going to stay in the same position at the same company our entire lives. Gone are the days when people would rise through the ranks within their corporation, landing themselves stability and community for decades on end in the same place. While it’s perfectly normal to rise through the ranks, career moves are a different game than they were in the past.

One of the most incredible resources you can find in your life is a mentor. A mentor is a successful person in your field who has time and experience under their belt and a proven track record that could potentially benefit your career track. Most importantly, they are willing to build a working relationship with you and guide you through thoughts, questions, and concerns you may have when approaching career pivots, moves and growth. Mentors are often professors, higher-level coworkers, C-Suite members or upper management and professionals in your workspace with expansive networks.

So, what is it about a mentorship that is really important for maneuvering your career goals?

Mentors have achieved proven success

As noted, mentors usually have more experience in your field than you do. Professors you may have had at university can glean some knowledge, as they have both hands-on experience, and have been able to guide and mold young minds in that specific area as well. Mentors know what it takes to succeed in your career field, and often have proven success. Learning about their journey and heeding their advice can help improve your career trajectory.

Mentors can provide guidance

Depending on the way their career unfolded, mentors can greatly shape your professional journey. Have an idea for how to move through a new project at work? See if they have any feedback. Applying to new positions? Let them know, and see if they have any interview advice or thoughts on how to approach a writing concept for your application. If you find the right person, they can even work off of intuition based on their own career experience. It is helpful in most cases to simply have someone in your corner to steer you away from total chaos and confusion.

Mentors have networking experience

Not only does the right mentor in your field have a Rolodex of essential contacts and influential people in the space, but they have networking experience under their belt. So, even if they are not personally familiar with the Head of A&R at a major label, they may know their assistant or have met the marketing manager at an event. Even when their networks don’t necessarily overlap with your career trajectory, they have experience in the networking space and can give you advice on how to meet new people, handle new contacts and nurture relationships.

Choosing a mentor

Finding a mentor isn’t necessarily the easiest task – it isn’t advisable to just go with the first person you see who has approached a similar career path. Choosing a mentor in the first place takes research, a bit of intuition and a whole lot of faith. Make sure to meet with them before committing to a working relationship, like a phone call, video conference or in-person experience will familiarize you with their cadence and personality. These can be integral to consider how you may work together.

Ensure that your potential mentor shares your values so that you do not get yourself into a position where the wrong priorities are being upheld. Look closely for someone who has achieved similar goals or career pivots to the ones you’d like to go after. The right mentor will help you move through your career, sifting through opportunities with a fine-toothed comb and encouraging you the whole way. Approach someone who has the bandwidth to nurture your relationship and work through different paths with you.

In this regard, it is also important to be able to offer your mentor things they may be needing in their career. This can include feedback – both personal and in the public review space – networking opportunities within other industries and a different perspective. It has to be a give-and-take relationship, though most mentors will simply be honored that their work and personality are respected and revered.

Important questions to ask your mentor

Once you have found someone who you are comfortable speaking with about your potential career path, there are so many places to start when discussing everything. We have put together a list of questions to help kickstart your conversations. It includes thoughts you can revisit over the years with your mentor, as well as other mentors you may encounter along the way. Who knows? Maybe you can refer to these questions when you, yourself, have a mentor or two that look up to you in your future position.

Let’s dig in. Here are great questions to ask a mentor the next time you are able to sit down and talk:

  1. Was there a moment when you realized you wanted to do what you do now?

  2. What was that spark of inspiration like?

  3. What inspires your work now?

  4. How do you approach your work when you feel a mental block toward it, or are feeling uninspired?

  5. What’s the best advice you can give to help plan and inspire a career?

  6. What are non-negotiables for you when it comes to choosing a company or client to work with?

  7. How have you learned to embrace risk-taking?

  8. Do you have a personal mentor? If so, how did that relationship come to be and what have they taught you?

  9. Would you consider your work a passion? Or do you try to separate work from your passions?

  10. What is an important leadership lesson you have learned?

  11. Do you find balance between your work and home lives? If so, how do you approach that?

  12. Do you have a ritual or routine that you have found benefits your productivity or environment?

  13. What is the best way to prepare for a performance review?

  14. How do you keep your feelings separate from your decision-making, if the issue arises?

  15. How do you stay on top of industry news and updates?

  16. Are there particular websites, periodicals, social media accounts, books or other options I should be following to stay ahead of the curve?

  17. Does your work benefit from networking-specific events? If so, which ones do you actually enjoy?

  18. How can I politely communicate to my coworker that I thrive without micromanagement?

  19. What do you do to constantly challenge any limiting beliefs you may have and open your mind to new perspectives?

  20. What is your favorite way to start the day?

  21. How would you have done it all differently, if given the chance?

  22. What are your core values when it comes to work environment and productivity?

  23. Do you know anyone who works at X, Y or Z companies that I could connect with about a potential opportunity?

  24. Would you be willing to be a reference on my job application?

  25. What are some important questions to ask during my interview for X position at Y company? 

  26. How do you handle setbacks in the workplace or during the application process?

  27. How do you keep your motivation high while looking for new opportunities?

  28. Do you think this networking happy hour will boost my chances at getting hired at X company?

  29. I am considering X job at Y company and M job at N company. Given our relationship and your experience with the way that I work, do you have any thoughts on which position would be the best fit for me moving forward?

  30. Is there a personal quality or skill you’ve developed over time that you consider essential for your work today?

  31. On a scale from 1-10, where 7 is not an option, how would you rate your satisfaction with your professional, financial and personal life at your current state?

It is important to remember that, even if you have a more casual or personal relationship with your mentor, their time is incredibly valuable. Keep your thoughts succinct during a mentorship meeting, or build them into a natural conversation while out to drinks or coffee. Your thoughts and questions could potentially inspire their work, so you want to make sure you are filling your time with prepared material as often as possible. As always, emphasize your gratitude for their willingness to work with you.

In the meantime, here are some great tips for when you do get that job of your dreams.

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