25 Questions to Ask a Mentor (and 5 Questions to Avoid)

Finding the right type of mentor can catapult your career, but you also need to ask the right questions. The best questions to ask a mentor are those that help you better understand yourself and extract the best insights. Because mentoring relationships are mentee-driven, effective mentees should have a list of questions to ask a mentor that drives the conversation and gets results.

If that makes you a bit nervous, we get why. There are good questions for mentors, and there are questions that don’t get any results at all. Not everyone is good at probing their mentor for answers. The following 20 questions should give you a good starting point for improving communication with your mentor and achieving your mentoring goals.

5 Questions to Ask a Mentor: First Meeting Suggestions

The first meeting you have with a mentor is critical. Even if your company is using mentoring software to create better, more cohesive matches from the start, there’s a little dance that mentors and mentees do during that first meeting that’s common with these types of relationships.

👉 Mentees are usually filled with questions and anxiety over what to say and how to lead in their own personal development.

👉 Mentors may also feel the same level of anxiety, wondering if they’re capable of helping their mentee progress and succeed.

To help your mentoring relationship get off on the right foot, consider making one or all of these your go-to questions:

1. We’re matched because the experience, skills, or insights I want to learn are something you’ve acquired through your own personal and professional development. Can you tell me more about how you got to where you are today?
2. Can you share a significant challenge you faced in your career related to our mentoring focus and how you overcame it?
3. What information do you need from me in order to be more successful in your mentoring role?
4. What are your expectations of me as a mentee?
5. How can I best prepare for our future sessions to maximize our time together?

There’s a chance you’ll feel a bit weird being so direct within the mentoring session. After all, most learning relationships don’t put the person learning in the driver’s seat. However, mentoring is mentee-forward. As the mentee, it’s your job to decide what you need, and to utilize your mentor as a resource for helping you get there. Asking the right questions can help them better determine how to point you in the right direction.

20 Questions to Ask a Mentor

Mentorship relationships work when mentees ask the right questions for their professional development and career path. However, it is easy to get caught in the moment and be in awe of the brilliance of your mentor. To help you stay on track, here are some of the best questions you can ask your mentor.

Some of the following questions may be open-ended, but you can tailor them to align with your specific interests and goals.

Questions on mentorship itself

• Why did you want to become a mentor?
• What do you want to get out of this mentor relationship?
• How often do you want to meet?
• How do you want to communicate?
• How can I come more ready for our scheduled meetings?

Questions on personal experience

• Where do you find your inspiration?
• What values do you find most important in a person? How do you commit to these values?
• What are your strong and weak traits?
• How do you get a better work-life balance?
• What are your interests, hobbies, and/or things you do outside business hours? How did you get interested in those things?

Questions on professional experience

• What are the biggest challenges and most important lessons you learned in your career?
• What life skills have been most beneficial in your career?
• What are the things I need to learn and develop to help me advance in my career?
• What is one lesson you can teach your younger self?
• What gives your job meaning?

Questions on your personal and professional growth and career development

• What are the most important skills you think I need to work on?
• What areas in my career do you think I need improvements on?
• Did you have professional development courses? What do you recommend I should get?
• What do you think is popular entrepreneurial advice most people don’t understand?
• How can I stay positive in my current position, career, and chosen field?

Bonus: Questions on career transition

Things may not always go your way, and there are times when you need to change careers or transition in a new direction within your current one. When working with a mentor, there is a good chance your mentor went through similar dilemmas. Don’t be afraid to ask about how they overcame those challenges.

• How do you know it is time to change careers? What are the first steps you need to take?
• How do you find meaning and purpose in your career?
• How do you find a job that fits your interest and passion?
• How can I be more proactive in carving my own career path and future?
• Will changing my career hurt my professional reputation?

Why You Need to Find a Good Mentor

These questions to ask a mentor will come in handy, but that’s only if you have a mentor at all. Finding a good mentor is often not easy, but it’s important.

Here’s an unpopular opinion — there is no such thing as being self-made. As the great American columnist George Matthew Adams once said:

Indeed, you are the by-product of your environment. Yes, you have to work hard, be smart, and be persistent to achieve your goals. But you also have to network and introduce yourself to the right people and make the right connections.

A huge part of your success is the result of contributions from your immediate circle, be it your family, friends, and, of course, mentors. Whether you are looking to join the Olympic wrestling team or become a world-renowned author, chef, startup CEO, or restauranteur, you will need the help of others. Everything in life is a team sport.

But like most things in life, finding the right mentor requires forethought, hard work, and in the workplace, a lift from matching tools that can help you find a mentor that matches your personality, interests, and needs. You have to find someone you look up to and want to be like. Then, you have to work with that person, commit to the mentorship relationship, evaluate your progress, and trust the process.

Moreover, to get the most out of your mentoring relationship, you need to know how, what, and when to ask the right questions.

First Steps to Prepare for Meeting a Mentor

The first step in the process is to find a good mentor. There are several ways to do that. There are two real ways to do this:

• Asking someone who’s succeeded in areas you want to grow in to be your mentor
• Joining a workplace mentoring program

The first of these might be a bit hard to do if you don’t know anyone who fits that criteria or you’re shy and unsure of how to approach that individual. A possible solution is to join a group mentoring program instead of a 1:1 mentoring program. That way, you can still get mentoring from someone with the needed experience but under much less pressure.

Other types of workplace mentoring programs are ideal, as well. Typically, you’ll get matched into the program by the program administrator. When mentoring software is involved, that process includes filling out a personality and interest survey that will match you up with someone using modern matching algorithms that are proven to produce higher-quality matches.

Once you have found someone who you believe may be a good fit for you, it is time to prepare for your meetings. It doesn’t matter whether it is your first or subsequent encounters; you need to establish your goals ahead of your meetings, seek consistent and continuous engagement, and hold yourself accountable.

1. Establish your career objectives

Mentors are often leaders in their field. In the corporate world, they usually hold executive and managerial positions. They manage different people and deal with multiple tasks in a day. Executives even mentor each other, so you’re not alone in seeking a mentor among the company leadership.

Because their time is limited, do the following before you go into your mentor meeting with a handful of questions:

• Consider what you need out of the mentoring relationship
• Write down important questions related to that goal
• Identify possible milestones to achieving that goal
• Outline how a mentoring relationship will help you through the process.

Are you looking for career guidance in your current position and role in your company? Do you want to climb higher on the corporate ladder and want your mentor to show you the way? What aspects and qualities of your mentor’s leadership and expertise do you want to achieve for yourself?

The idea is to learn as much as possible from your mentor and to develop certain expertise and skills. That way, once the time comes, you can step easily and confidently into the roles you want for yourself in the future.

Whatever it is you are looking for in a mentoring relationship, you need to establish your short-term and long-term goals to determine exactly what you want to achieve from your time together with your mentor.

2. Seek engagement opportunities

You need your mentors more than they need you; thus, it is your responsibility to seek consistent and continuous engagement and drive the relationship forward.

Take care of all of these engagement needs:

• Schedule meetings that meet their schedule and organize the agenda for each meeting
• Determine a good meeting cadence
• Decide on a meeting length that works for both you and your mentor
• Commit to your meeting schedule

Also, it is important to ask your mentor for his/her preferred communication method. Obviously, you cannot email or text your mentor over the weekend, on holidays, or late at night unless they specifically told you that you can.

3. Hold yourself accountable

Take notes (if not mental notes) after each meeting; write down everything there is to learn. Use AI note-taking software if your mentor will allow you to, or learn a shorthand note-taking method.

Also, many times, your mentor will give you assignments or engage you in mentoring activities and tasks to accomplish in between meetings. This is often the case with structured mentoring programs, such as onboarding mentoring or functional mentoring. Make sure to complete these assignments and be prepared to present them to your mentor in your next meeting.

There will be times when you cannot complete the tasks or commitments. If that’s the case, tell your mentor in advance so they won’t waste their time waiting for you.

How to Ask Your Mentor Questions

The best way to get answers and career advice is to ask the right questions, and for you to do that, you need to know how to formulate a good question in the first place. Here are some tips on how to ask the right questions to ask a mentor.

1. Make your questions specific, not vague

Keep the questions clear and relevant to your current topic and specific to the situation or lesson. People seek guidance from their mentors to solve specific problems in their professional careers. Mentors love that, as it gives them a chance to share their experience, specifically on how they handled and solved challenges in the past. It’s why mentoring tends to increase job satisfaction for both mentors and mentees alike.

Say you have a mentor to address your fear of public speaking. Here are a couple of questions you might ask:

• “How can I develop my public speaking skills?
• “How do you manage to handle nerves when speaking in public?”

While the first question may be relevant to your goal, it is a vague question that may require a much longer conversation to answer. The second question, on the other hand, is more direct and to the point. It allows the mentor to answer quickly and completely, without spending hours trying to explain everything.

Your mentor may share tips on how they psyche themselves up to face a huge crowd and how they prepare their speech or presentation.

2. Focus on topics that aid in career advancement

Know how to ask questions that lead to meaningful conversations.

Here are a few examples:

• Should you want to learn more about your mentor’s expertise then ask for specific advice on how they developed and continue to refine their skills.
• Ask them to share stories about how they networked with industry leaders and leaders within your company to advance their careers.
• For people looking to build a startup, you can ask your mentor how they took huge risks and how things panned out. This question gives a really good insight into how they manage risks, foresee challenges, and solve those obstacles.
• Ask questions specific to the situation.
• Don’t be afraid to ask for clarifications and circle back to your conversation to make sure you understand and follow your mentor’s advice.
• Have a sense of accountability as a mentee. Ask your mentor how you can improve as a mentee and make your mentorship work for both of you.
• If you are starting a business, then you need to ask your mentor how to become a better leader. This involves knowing how to handle multiple people with different personalities and egos and resolve conflicts within your team. Moreover, ask your mentor on how to handle different aspects of your business better and the habits needed to build to become a successful entrepreneur.

3. Seek meaningful advice, but connect with small talk

Keep the conversation meaningful, but don’t avoid small talk. Making connections with your mentor is important. Multiple studies show that small talk builds rapport and will lead to larger and more important conversations. It’s also a healthy and effective way to establish and sustain relationships at the surface level that then move into deeper engagements.

4. Always come prepared

As said earlier, your mentor’s time is extremely valuable. Thus, respect their time by coming in prepared. Also, this is the best way to get the most out of your mentoring program. Ready your questions and listen intently so you can make your follow-up questions.

5. Use questions as a conversation starter

Identify the different ways you can build your career by asking questions that lead to actionable advice. Seek networking advice, ask how you can improve your leadership qualities, speaking, and presentation skills, etc.

5 Questions You Should Never Ask Your Mentor

While it’s important to ask the right questions, there are some questions or topics that you should never ask a mentor. The reasons for that vary, from the wrong timing, to topical sensitivity. Assuming you’ve signed a mentoring partnership agreement with your mentor, you may have an idea of what questions are off the table. If you haven’t, make sure you have a conversation with you mentor so you know what’s appropriate and inappropriate to ask.

With that said, in almost every mentoring relationship, these 5 questions are going to be no-gos:

Questions about your mentor’s finances

“How much money do you make?” or “Can you give me details about your personal finances?” are questions you should never ask your mentor unless you’ve received permission to discuss these topics. These types of questions are overly intrusive and may be irrelevant to your mentorship goals.

That said, we’re all for financial transparency in the workplace. People like Hannah Williams, who launched Salary Transparent Street, have helped remove the stigma around asking about salary in the workplace. Nevertheless, the question can still make many people uncomfortable, so if you want to broach the subject, ask for permission before blurting out the question.

If you do want to know more about salaries, especially if your mentoring relationship is focused on career development, start by researching salary ranges at places like Salary Transparent Street, ZipRecruiter, and Glassdoor. Job postings on LinkedIn are also a good source to get an idea of what someone within a specific role may be earning.

Requests for unethical assistance

Questions like “Can you help me get around company policies?” or “Could you give me the answers to this test/project?” fall into this category.

Asking a mentor to engage in unethical behavior or to circumvent rules puts them in an awkward position and reflects poorly on your character and judgment.

You will likely lose the respect of your mentor and ruin any chances you may have had of having that mentor volunteer to sponsor you for internal promotions or high-profile projects.

Excessively personal questions about their personal life

Asking questions like “Can you tell me about your personal relationships or family issues?” is generally off-limits, unless you and your mentor have agreed that such topics are acceptable.

While some personal rapport is essential, delving too deeply into a mentor’s private life can be invasive and inappropriate. Effective matching quite often leads to mentor-mentee relationships that feel exceptionally natural. So much so, in fact, that a mentee can’t be faulted too much for forgetting that there are professional boundaries to maintain in that engagement.

We’ve heard many tales of mentors and mentees becoming great friends after the mentoring relationship has ended, and that’s perfectly fine! However, while your workplace mentoring relationship is active, try not to delve too deeply into the familial.

The focus should remain on professional development, skill development, and othe goals as guided by the program.

Direct comparison questions

These consist of questions such as “Am I better than your other mentees?” or “How do I stack up against your colleagues?”

These types of questions put the mentor in an uncomfortable position of making comparisons that are often subjective and unproductive. They can also create an atmosphere of competition and insecurity rather than learning and growth.

We likely don’t need to add much more to why these questions would be inappropriate except for this: If you like your mentor and they support you and help you succeed, that’s all that matters.

Inappropriate requests for favors

“Can you recommend me for a promotion?” is not something a mentee should ask. There’s a defining line between mentorship and sponsorship. Not all mentoring relationships lead to sponsorship. Generally speaking, mentees should not be asking their mentors for promotional favors. Let the mentor determine when the time is right for that and if that’s right at all.

While a mentor can provide guidance and advice on career progression, it’s inappropriate to ask for personal favors or to leverage the relationship for unfair advantages. This can strain the mentor-mentee dynamic and lead to an imbalance in the relationship.

Remember, the key to a successful mentoring relationship lies in mutual respect, professional boundaries, and a focus on growth and learning. Avoiding these types of questions can help maintain a healthy, productive, and respectful relationship with your mentor.

The Bottom Line: Ask Your Mentor Questions, Then Take Action

If you want to be successful in whatever you choose to do, you need to connect with the right people. People who can guide you through the intricacies of your chosen field, the ins and outs of your chosen career, and help you develop and grow to be a better version of yourself.

This is what a mentorship program is about. It helps you carve your career paths, develop the key skills you need, find the meaningful answers to your most important questions, and ultimately, achieve success.

Once you’ve landed a great mentoring relationship, started meeting, and begun asking the hard questions, don’t forget to take everything to heart and take action. After all, there’s no point in spending time with a mentor if you don’t plan to be actionable.