Jennifer Herrity
Updated November 2, 2022
Published October 7, 2019

Jennifer Herrity is a seasoned career services professional with 12+ years of experience in career coaching, recruiting and leadership roles with the purpose of helping others to find their best-fit jobs. She helps people navigate the job search process through one-on-one career coaching, webinars, workshops, articles and career advice videos on Indeed’s YouTube channel.

A mentor is a trusted industry expert who can offer you advice and guidance as you progress in your career. The right mentor can help you outline a clear career path and choose steps to achieve your professional goals. Learning about questions to ask mentors may help you in future meetings.

In this article, we explore nine specific questions to ask your mentor so you can optimize this professional relationship.

A mentor often offers career advice, skills training, networking opportunities and references for your job search. While many people choose mentors in their own field, you may also choose an advisor in another industry to provide broader career insights. The following questions can help you learn from your mentor’s relevant experiences, identify opportunities for professional growth and better understand how you’re seen in the workplace:

Here are some sample questions with insight you might gain from asking each:

1. How did you pursue your career?

Mentors are typically in a more advanced position on a career path similar to yours. As a result, understanding your mentor’s journey may help you refine your own professional path. You can learn the typical steps in this profession, including education and early jobs and what you want to achieve at each level of advancement.

Perhaps your mentor pursued opportunities outside of the typical career path that provided many benefits. Your mentor’s professional journey can serve as an outline to follow or provide you with options you had not considered.

2. What’s an obstacle you encountered, and how did you handle it?

Overcoming obstacles is essential to succeed in any career. Your mentor has likely faced challenges similar to those that you may encounter in your own career path. You can use your mentor’s experiences to help you anticipate issues and prepare your own response.

Ask your mentor how they feel about the results of their reactions to obstacles and what steps they took to remain focused on their goal while encountering setbacks. You can learn from their successes or discover ways they may handle the situation better had they known what they do now.

3. What career accomplishments are you most proud of?

Career accomplishments can include earning promotions or subtle successes, such as conquering a small but challenging issue. Consider discussing the accomplishments that gave your mentor the greatest sense of pride to help you establish your own career goals. Your mentor’s perspective on career accomplishments can encourage you to value improvement and measurable success.

4. Have you read any books that helped you develop your career?

There could be many resources that helped your mentor on their professional journey, from fictional works with valuable messages to nonfiction books on productivity or leadership. This question can lead you to a variety of literary works filled with information and inspiration for your professional journey.

Discover what books your mentor has learned the most from and consider reading these books yourself. They may also be able to provide you with other helpful resources, such as documentaries, podcasts, online interviews or presentations.

5. What do you see as my strengths?

Understanding the skills you excel in using can help you identify the professional opportunities that are best suited to your talents. Your mentor can help you assess your strengths objectively, providing you with a list of skills you can mention on your resume or use during your next job search. You can use your mentor’s assessment to answer interview questions about your strengths, including examples that demonstrate how you use your strengths to complete tasks and achieve goals.

6. What can I improve?

You can advance your career by improving areas that require development, but you may not be able to see your own weaknesses clearly and objectively. Seek your mentor’s guidance on career-related skills you can improve. Your mentor may be able to help you find resources such as continuing education, additional training or potential practice opportunities.

7. How do others view you?

Mentors can help you gauge your abilities accurately and understand where to apply your skills and talents optimally in a workplace. If your mentor works in the same company, they can give you an idea of how your coworkers or managers perceive you.

A mentor from a different company may have insights into your overall reputation within your industry. This information can help you improve your strengths and address areas where you may like to change others’ perceptions of you for the better.

8. How can I prepare for my performance review?

Performance reviews are annual meetings with your supervisor or employer that reward your success and encourage your improvement. Your mentor can provide insights into what to expect during your performance review, especially if you are in the same company. They can also offer advice on responding tactfully to the feedback you receive.

You may try role-playing important interactions during this meeting, such as taking criticism or asking for a raise. Performance reviews help you set goals for improvement within your company, so preparing with your mentor for these meetings can ensure you continue on your intended career path.

9. What’s your leadership style?

Effective leadership skills are essential if you want to advance into a management role. Discover what philosophies your mentor finds useful and how these have impacted their ability to successfully lead others.

You may choose to utilize these leadership techniques or adapt them to your own style. For example, if you usually attempt to be an active and participative leader, you may try a more passive and independent style.

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