What to Ask a Mentor: 15 Things You Don’t Want to Forget

You are new to the job and are trying to figure things out. A colleague tells you that there is a program for newbies where you get matched with a mentor. This is a fantastic opportunity!

You’ve never had a mentor before so are unsure about what he or she will really help you with. Your boss says not to worry and sets you up with a seasoned mentor who is a good match.

The first task you have as a mentee is to meet with your new mentor and ask any questions that you may have.

If you were actually in this situation, would you know what  to ask a mentor?

The benefits of a mentor and why you should know the RIGHT questions to ask


The benefits of a mentor and why you should know the RIGHT questions to ask What to Ask a Mentor | Wayahead

If you’re reading this, then you probably already know the basic benefits of mentorship. You understand that having a mentor can help you to boost your current role within your career. Mentorship can give you the resources you need to guide you down your chosen career path.

But just to jot your memory, there are many fantastic benefits of a mentoring relationship.

Professionals at the University of the People list 7 Benefits of Mentoring Programs in the Workplace.

  1. Improved personal and career development
  2. Improved onboarding and productivity
  3. Leadership development
  4. Builds diversity
  5. Allows for reverse mentoring
  6. Supports a learning culture
  7. Reduces costs

What mentees can get out of the right mentoring relationship:

  • Career and job-related skills such as problem-solving, presentation, or technical skills
  • Study or time-management skills such as getting tasks done before a due date
  • Education/academic-related skills such as writing a research paper
  • Specific life skills such as cooking, applying for jobs, getting around a city
  • Relationship skills such as communication or working through conflict
  • General people skills such as social skills or working with different personalities

Now, these types of benefits won’t just be handed to you. It’s time you start thinking about the types of questions to ask a mentor so that you may get the perfect one for you.

The importance of strategic mentor questions

The importance of strategic mentor questions What to Ask a Mentor | Wayahead

Do you now understand the great success you can have from being a mentee? Choosing the right mentor is so important to your future success. You want to be prepared when you two first meet. There are hundreds of questions to ask a mentor; however, you will want to be strategic in the questions you choose for the conversation to benefit you the most.

What if you only want to ask him/her one or two things? Is that actually realistic of you to only ask your mentor one thing?

Honestly, that is not enough. Mentorship is more involved as this is going to be the person who will work with you one-on-one.

Take some time to brainstorm questions that you may like. Browse Google (or read this article!). Talk to other people for their opinion and advice. It’s not something you have to jump into; you can take the time you need to prepare to ask your mentor the best and most important questions.

Once you are sure you have the perfect list, set up a meeting with him/her—this may be with the company you work for or as a professional meeting at another location.

Next—learn about important questions mentees often ask their mentors. See if you like any of them and might use them with your own mentor.

15 Questions you Shouldn’t Forget to Ask Your Mentor

15 Questions you Shouldn’t Forget to Ask Your Mentor What to A Mentor | Wayahead


One thing you should understand is that when you get a mentor, you do not only gain a partner to help you along your career path, but you may also gain a friend and confidant. Mentoring relationships are special ones. By asking him/her a personal question, you will be able to learn more about the actual person. Most career relationships are built off rapport. So think of a thoughtful question to ask a mentor.

  1. What made you choose to go into mentoring?
  2. Who is someone in your own life that has made a powerful impact on you?
  3. What strengths and qualities do you possess that make you stand out as a mentor?

By asking these, you will get to learn a little about your mentor’s past, what they like, what they dislike, etc. You will also gain insight into why they believe mentoring is so important and what they can contribute to a mentee.


Asking a career-based question will allow you to learn how your mentor can help you to reach your business goals. You may ask him/her about their own career and/or how they plan on helping you better yourself in the industry.

  1. What has your greatest challenge been within your own career path and how did you overcome it?
  2. How specifically do you think you can help me achieve my career goals?
  3. How will you help me to balance work/school/life to get ahead on the job?

Career-based queries should be at the top of your list to ask. You will learn a lot about how they believe they can help you become more successful in your career. If they don’t provide you with the answer you’d like, then you may need to think about interviewing other people.

Skill-Based What to Ask a Mentor | Wayahead


By asking a skill-based question, you are getting down to the nitty-gritty. You want to know what specific skills this person can help you with to improve in order to further your career.

  1. What specific skills are you exceptional at that you can teach me?
  2. What are new, modern skills that you think I should know that will help me to get ahead at my job?
  3. Are there skills you think I am wasting my time on that is not benefiting me in furthering my career?

The skills you learn from your mentor are what is going to drive your career forward. Question their own skill level in areas that you are interested in knowing more about. Inquire about their credentials and experience. Don’t be shy; he/she will expect this from you.


Learning-based queries go right along with skill-based ones. This is the ‘how’. How your mentor will teach you skills is important. Aren’t you interested in the type of learning that will be taking place?

  1. How will you specifically teach me the skills that I need to learn, i.e., digitally, in-person sessions, by networking, via books, in small professional groups?
  2. Will we be working directly with other people during our learning time together?
  3. How often will we meet and how long do you expect our mentoring relationship to last?

After hearing what your mentor has to say about the learning process, you may or may not like what they have to say. Go into the interview with expectations. Be clear with your mentor about what you want and need out of your educational time together.

Success-Based What to Ask a Mentor | Wayahead


Reaching your goals and being successful is the end game. This is the entire point of your mentee-mentor relationship.

  1. How do you monitor mentee success along the way?
  2. How do you approach a mentee that is struggling to meet goals or is falling behind?
  3. What do you do to keep your mentee motivated and to celebrate milestones of success?

You WANT to be successful—that’s WHY you are interviewing mentors. Make sure the one you choose is going to follow you on the track to success by supporting, teaching, and guiding.


Of course, there are TONS of other questions you can ask your prospective mentor. These are the five categories that you want to focus on when brainstorming your list of queries to ask. The person you interview is going to expect a lot of personal and career-based inquiries.

They are going to assume you’ll wonder how you expect them to guide you to where you want to be. Don’t hesitate to inquire with bold and daring questions. You don’t want to leave the interview with regrets.

Ask the right questions to the answers you want to hear. You’ll find the perfect mentor in no time!


Angel Santiago
Servant Leader | MBA | Veteran | Founder @ wayahead.io

July 16, 2020



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