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15 Strategic and Essential Questions To Ask Your Mentor

  • Omer Usanmaz
  • August 22 2023

To make the most of your mentorship program, you should be able to ask relevant questions to your mentor openly. Mentors are trusted and experienced industry professionals who can offer appropriate advice and guidance to help you progress in your professional career. The right mentor can undoubtedly help you define the career path you want to pursue and identify ideal ways to help you achieve your professional goals.

But often, mentees fail to grab the opportunity to interact with their mentors and ask irrelevant questions during their mentor meeting. Therefore, mentees must ask the right questions to their mentors and seek advice that sticks. This blog post will explore the most relevant questions that the mentees should ask to genuinely benefit from the mentorship relationship and make your mentorship experience memorable, helping you avoid asking bizarre questions.

List Of Important Questions to Ask Your Mentor

It is essential to know that your mentor is a highly experienced and skilled person capable of offering you the right career advice to help you with your career trajectory, networking opportunities, skills enhancement guidance, and references to help you with your job search. Furthermore, mentors can be chosen from within one's field or selected from another industry with a broader understanding of various fields and career insights. Let's explore the best types of questions that you can ask to your mentor to get the best of your mentorship relationship and achieve career development goals and mentoring goals:

Begin with the Icebreakers

Everyone likes to talk about themselves. To get started, asking your mentor about themselves is a good strategy. In the context of Mentorship, you break the ice by asking questions such as "What made you decide you wanted to pursue this as a career?", "How did you get started?" or "What was your first job like?"

But the questions can also be more focused on your career objectives. Let's consider some of these common mentorship questions to ask your mentor about career development:

  • Did you ever apply for a job you thought you weren't entirely qualified for?
  • Did you ever feel you made some consequential errors or biggest mistakes, and how did you bounce back?
  • What is a valuable advice that you can give me to start successful mentoring relationships?
  • Any recent setbacks you may have suffered in your professional career, how did you resolve them?
  • How do you stay productive, and how do you maintain a work-life balance?
  • What were your career path options when you began your business journey?
  • What would be a good networking advice that you can give me? 

To the Lighthouse: Your Mentor's Career Path

"How did you choose this career path?"

Getting more into the specifics, asking this crucial question can help you understand your mentor's journey and help you align his experiences with where you are today in your career. It can help you comprehend some of the most common mistakes or hindrances while on your career path, the type of skills and education you will need to advance, and the core skills required to improve professionally. Your mentor's professional skills and the journey can outline your career path and should be ardently considered. 


The Thorns that Might Get in Your Way

"What are the common obstacles in this career path?"

Overcoming persistent obstacles in your career path is crucial, and understanding these hindrances can help you succeed in your career. Asking your mentor about the significant barriers they have faced in their careers is very helpful, as your mentor, with his experience as a career mentor, has probably faced more biggest challenges which you might encounter too.

Your mentor's experience can be considered while anticipating similar challenges and preparing proactively for your response. Ask fundamental questions to your mentors about how they responded to the most difficult challenges they faced and how they remained focused on their path, despite facing difficult setbacks.

These questions can help you learn from their experiences, as occupational hazards and obstacles are inevitable. But if you know how these challenges can be resolved by someone who has already faced them, it will help you prepare better.


Learn Deep: The Proudest Accomplishments

"What accomplishments are you most proud of in your career?"

Getting a response from your mentor about their career accomplishments and professional experience, earning promotions, and overcoming small and big challenges can help you establish your own professional goals and improve your career prospects. Asking these kinds of questions can help you set the benchmark and the performance standards you should strive for, helping you make the most of your mentorship experience.


Ask for Recommendations to Get Insight

"Can you recommend any resources, books, or authors who have helped you progress in your professional career?"

It may be uncommon knowledge, but most successful mentors, entrepreneurs, and successful people have authors and books that have significantly influenced their career pursuits.

The recommendations made by your mentor can introduce you to various literary works, replete with helpful information and inspirational stories which you will be able to relate well with your current role and the career path you are on. It can also help improve your mentor relationship.

Furthermore, ask for book recommendations that inspired your mentor the most, his key influencers, and try and read them yourself. It may also lead you to discover helpful resources, including documentaries, interviews, podcasts, and more.


Learn about Your Strengths

"Would you mind processing my key skills and strengths?"

Understanding the areas you excel in and what you are good at can help you identify potential tasks and projects in which you can feel most confident. Your mentor can assist you in evaluating your skills more objectively.

Your mentor can also help you identify your key strengths, which you can put on your resume or use during your job search. Your mentor's assessment can help you have meaningful answers to your questions about your vigor during an interview, along with examples that can show how you can use your strengths to complete tasks and achieve your goals.


Understanding Areas of Improvement

"In which areas would you recommend me to improve myself?"

Career advancement is inadvertently dependent on improving areas in which you need development. Seeing one's weakness clearly and objectively isn't ideal. Therefore, during your mentoring session, you should ask your mentor for advice in identifying areas of improvement, what your blind spots are, what you can do to get better and what resources you can use to bring about the desired development. It could be seeking further education on a particular topic, additional training within a specified field, or working directly under a senior and observing how they work. This question can significantly help you with your growth ambitions.


Learn about Your Co-workers' Perception of You

"How do I look from the outside?"

Understanding how your colleagues, subordinates, and superiors view you can help you foster better mentee relationship with them. Your mentor can help you understand how they see you and the skills and talents in you they appreciate. If your mentor is in the same company, he can help you learn how your workers and co-managers perceive you. If your mentor is from outside the company, he can help you gain insights into how others in the industry discern you. These insights can help you enhance your strengths and address areas where you'd prefer people had a different opinion about you.


This Time of The Year: Consult about Your Performance Review

"How to successfully prepare for a performance review?"

Annually, most companies will have a performance review session between your supervisor or your reporting manager to reward your success and to suggest improvement wherever it is required.

Consulting your mentor about performance reviews can help you get insights into the general expectations from such activities. They can also provide valuable insights, such as responding correctly to the valuable detailed feedback you may get. Some mentorship programs also involve a role-playing scenario to prepare yourself for pivotal interactions, such as receiving criticism to excel the career journey or asking for a pay rise.

Most importantly, performance reviews can help you define goals for improvement in your company. Therefore, it is crucial to communicate with your mentor about career path, expectations, questions, and responses expected from performance reviews, helping you better prepare for them.


Seeking Advice on Specific Instances and Situations

During your employment, you may come across difficult situations and not respond appropriately. It may be an unfair criticism from your supervisor, or if you notice someone mishandling a particular project - should you inform your superiors about this, or should you keep quiet for fear of retaliation? Dealing with such situations can be difficult if you are in a junior position. To better prepare for such events and to make the most of your mentorship experience, consider asking the following list of questions to your mentor:

  • How should I start a conversation about my promotion?
  • How can I develop my public speaking skills?
  • I am working on projects that may not suit my skill set. I want to work on tasks where I can use my proper skills. How should I approach this?
  • How can I provide constructive feedback to my teammates?
  • Should I consider accepting a job offer I have received?
  • My salary is less than what my peers are making. How do I ask for a raise?


Understanding Your Mentor's Leadership Style

"How can I incorporate your leadership skills into my practice?"

If you are impressed with your mentor's leadership skills, asking them how they can be applied to your practices is one of the most critical mentoring questions. Learn about the philosophies or ideas which inspire your mentor. Understanding some of the essential leadership traits that your mentor finds extremely useful can also help you adopt and implement those values in your professional life.


The Importance of Learning Soft-Skills

"How can I improve my soft skills?"

If you are an early career professional, you may not clearly understand where and how to go to your desired destination career-wise. It can get uncomfortable hearing about the lack of certain behaviors which may be standing in the way of your goals. Many professionals will agree that it is far easier to learn a hard skill, such as a programming language. But it is challenging to learn soft skills such as how to communicate effectively, form professional relationships, handle conflicts productively, accept responsibility for your mistakes, and hold others accountable.

For better management aptitudes, soft skills are fundamental. Besides the benefits of learning soft skills for professional development, they can also help your personal development journey.


What We Learned from Failures

"How have failures impacted your success?"

Asking questions about failure can bring forth unpleasant memories. Mentees often shy away from asking this question. But if your mentor is ideal, he will undoubtedly share his personal experiences on occasions where your mentor has failed. As a best practice, ask their permission before posing the question. Learning from your mentor's mistakes can help you avoid similar pitfalls and help you better prepare for the career path you are on.


Count on The Importance of Diversity

"Are there any industry experts who can provide more insights?"

Traditionally, asking such a question would perhaps imply that you are not adequately satisfied with the guidance your present mentor is giving you. But modern-day corporations understand the importance of diversity and have different opinions about professional topics.

Asking advice for networking to your mentor is helpful because your mentor will better understand what will genuinely help you. Being in the industry with significant experience, he can aptly suggest another mentor who will be more suited to address a particular aspect of the mentorship program.


In The Turnout Point to Have A New Start

What is your take on making a career change?”

Your mentor's experience and insights can benefit you when considering a career change. With all their experience, your mentor can guide you through transitioning to a different position within the company. Or you can get meaningful advice on moving to another job.

For instance, they may have worked at a company you are considering, or they may know someone who can get you a job. If you are seriously considering a career transition, your mentor will be the best person to seek guidance from, and he can surely give you actionable advice.

Changing careers is a critical decision, fraught with risks. Discussing with your mentor the reasons for your decision to change your career can help you get a comprehensive understanding of your possible options. These decisions are never easy, but getting an opinion or guidance from an experienced mentor can significantly help and serve as a valuable leadership lesson.

Other questions That Can Be Asked


What is your preferred method for handling stress during busy workdays?

How do you choose the most effective method of communication for different situations at work?

If you could give one piece of  entrepreneurial advice to aspiring entrepreneurs, what would it be?

How has having a mentor influenced your career choices and development?
Could you share your daily routines that have significantly improved your productivity?
What was your biggest fear when starting your first position, and how did you overcome it?

How do you ensure that you maintain a positive professional reputation within your industry?

What do you find most rewarding about being in a management role?

The Bottom Line: Good Communication Skill is A Must

Preparation is crucial for a mentorship program. The above-listed 15 questions will help you avoid confusion or awkwardness, and it will ensure that you are not wasting your mentor's time by asking irrelevant questions and that you seek appropriate career advice. Additionally, do not hesitate if you feel there are even more relatable questions you would like to ask your mentor besides the ones mentioned above for your personal growth.

Most importantly, be authentic. Mentorship is all about building a robust successful mentorship relationship. For an authentic and strong mentor-mentee relationship, healthy mutual respect should be developed like all productive relationships, and effective communication should be maintained throughout the program. Your mentor should be able to address all your doubts and concerns. But if you fail to ask some critical questions, there isn't much a mentor can do to address them. Hence, ask the right questions and do not hesitate.

The path to career success is often tricky, and career progress may seem confusing. But having an experienced mentor can help you overcome obstacles and stay focused on your professional goals and current goals. But a mentoring relationship is a conversational one that includes meaningful conversations and difficult conversations. If you cannot clearly articulate your questions or ask mentor questions irrelevant to your career goals, the relationship will most likely collapse. Hence, take time to prepare for the most pertinent questions you would like to ask your mentor, as it can help you genuinely benefit from the mentorship program, build strong relationships and have a positive experience on your career growth.

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