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29 Questions To Ask Your Mentor In Your Next Meeting

What are good questions to ask a mentor? Every mentor/mentee relationship is different so don’t take a cookie-cutter approach. Prepare questions that feel right for you and that you think will help build a successful mentoring relationship. But, to help get you started, we’ve put together a list of ideas and conversation topics. 

June 8, 2021

It’s no secret that mentorship can have a significant positive impact on your career path — from higher salaries and quicker advancement to increasing satisfaction at work. But the benefits of a mentor/mentee relationship are dependent on the effort that both parties put in. After all, mentorship isn’t magic. It requires forethought and a dedication to growing.

A big part of doing the work is coming prepared to your meetings. When someone is offering their time and advice to help you grow, show them that you appreciate it by arriving prepared.

But what does showing up prepared mean? Unlike your project management meeting or your team meeting, mentorship meetings can be a bit more ambiguous and not as intuitive. You need to decide what your end goal is and what you want to learn from the relationship. 


How to prepare for a mentor meeting

Whether this is your first mentorship meeting or you already have an established relationship, you should prepare in advance of each meeting to demonstrate that you care and not waste your or your mentor’s time.

Don’t know where to start? Here are some tips 👇🏻

Prepare for your meeting with your mentor


Do your research

Similar to how you’d go into a networking meeting or a job interview, it’s crucial to look into your mentor’s background before you meet. Check out their LinkedIn profile to get a sense of their career path and give them a Google search to see what kind of cool stuff they’ve been up to. 

The reason it’s important to do research on your mentor beforehand is two-fold. Firstly, it’ll give you insight into their specific experience, allowing you to gain a deeper understanding of what information they can provide that will be specifically beneficial to you.  Secondly, it demonstrates your commitment to the relationship and shows that you value your mentor’s time.


Think about your goals

What skills do you want to develop? Where do you see yourself in three years? Do you want to expand your network? These are some of the questions you can ask yourself as you start to think about your mentorship goals

Most mentees will approach a mentorship relationship with a general idea of what they want to learn — otherwise known as starter goals. That’s okay before your first meeting. But, if your goals are too broad, you’re less likely to be satisfied with the relationship and its outcomes. That’s why it’s important that you ultimately develop more concrete SMART goals — specific, measurable, attainable, relevant and time-bound. You and your mentor can decide to develop SMART goals together.

Some goal examples could include: 

  • Do 5 informational interviews with people in X industry by X date.
  • Read X book by next meeting to discuss key take-aways on X topic
  • Update and finalize my resume by X date
  • Raise my hand for a new project at work that involves X skill I want to develop by X date
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Check your ego 

Most of us are used to getting constructive criticism from our direct managers or peers, but a mentor brings another, perhaps more objective, perspective to help us brush up on relevant skills. Having the opportunity to receive feedback from a mentor outside of your work team is an amazing way to gain a deeper understanding of your blind spots and how to improve.

So don’t get defensive about it. Be prepared to accept your mentor’s constructive feedback with open arms — how else will you grow?

Questions to ask your mentor

Okay, you’ve done your research, thought about your goals and are willing and ready to accept feedback. 

Now what? 

While allowing room for the natural flow of conversation is important, completely winging it is a risky approach. 

Think of some strategic questions to ask your mentor and conversation topics you’d like to talk about before your meeting. Even better, give your mentor access to the questions in advance using a collaborative meeting agenda. This will give your mentor the opportunity to show up prepared to speak to your questions and address your specific experiences.

What are good questions to ask a mentor?

Every mentor/mentee relationship is different so don’t take a cookie-cutter approach. Prepare questions that feel right for you and that you think will help build a successful mentoring relationship. But, to help get you started, we’ve put together a list of ideas and conversation topics. 

Take an interest in their life (without getting too personal)

While you need to prepare for your mentorship meeting, you don’t need to rehearse. Remember that ideally, your partnership is an authentic relationship and, therefore, should be nurtured like one. In fact, according to Anthony K. Tjan, your relationship should come before your mentorship. 

Sometimes, mentorship can turn into more of a transaction than a real relationship. But if you’re merely checking a box, the mentorship won’t be successful. So start by getting to know your mentor better and showing an interest in them as a person. 

  • How are you feeling?
  • What are you excited about right now?
  • What’s new since we last spoke?
  • How are you staying motivated?
  • What’s a goal you’re currently working towards?
  • What’s going on outside of work in your life?

Questions to get to know your mentor better
Ask your mentor these questions to get to know them better.


Set expectations for the mentor relationship

Off the bat, it’s a great idea to get on the same page about your and your mentor’s goals and how you’re going to achieve them together. These are especially important questions to ask in your first mentorship meeting, but also great to continuously check in and realign. 

  • Why did you decide to be a mentor? 
  • What are your goals for the relationship?
  • I’m keen to get your input on my goals for this mentorship. Can we review them together?
  • How often do you want to meet?
  • What’s your preferred method of communication?
  • How can I better prepare for our meetings? 

Questions to ask your mentor to understand their goals
Ask your mentor these questions to understand what they expect from the relationship.

Ask about their professional experience

Learning more about your mentor’s specific experiences, the challenges they’ve overcome, how they arrived where they are today and how they continue to succeed is invaluable. Take the time to discuss your mentor’s career, both past and present. This is where all that research you did will really come in handy!

  • Why did you decide to go into this field?
  • How did you move into X role?
  • What were some challenges you faced in X position?
  • What skills have been most beneficial for you?
  • How do you achieve work/life balance?
  • Do you have any networking advice? 
  • Are there any networking groups you think I should join? 

Questions to ask your mentor to learn about their professional experience
Ask your mentor these questions to learn about their professional experiences.

Seek advice on specific situations

Your mentor likely has a plethora of experience they can draw on to help guide you through your current challenges. If you’re having trouble navigating a specific situation, your mentor has probably been there before— or at least somewhere similar. Don’t be afraid to ask for help.

  • Do you have any advice on how I can approach discussions about a promotion?
  • I feel like I’m being pigeonholed at work right now and would like to try some new things. In your experience, what’s the best way to approach this?
  • If you were me, how would you have approached X situation?
  • Do you think I should accept this new job offer?
  • My salary isn’t in line with what my peers are making. How do I ask for more?

Questions for your mentor to get advice for a specific situation
Questions for your mentor to get advice for a specific situation.

Questions about how you can improve

Your mentor can provide a more objective lens on areas you can improve to help you succeed. Check your ego at the door. The more open you are to feedback, the more valuable guidance you’ll receive.

  • What skills would be beneficial for me to work on?
  • Where do you think I can improve?
  • What could I have done differently in this specific situation that may have improved the outcome?
  • Do you have any recommendations for professional development courses? 
  • Are there any good books you can suggest that would help me improve X skill?

Ask your mentor these questions to get help identifying areas of improvement.
Ask your mentor these questions to get help identifying areas of improvement.

Bonus: Questions mentors can ask mentees

Mentees aren’t the only ones benefiting from mentorship, and nor should they be the only ones putting in the effort. While mentorship is often viewed somewhat as a one-way street, mentors also gain significant benefits from the relationship. Beyond personal fulfillment, mentors gain valuable leadership experience, insights into a younger generation and fresh ideas. Plus, who knows where your mentee will end up in the future. It’s likely that the relationship will come full circle. 

So don’t take your mentorship role lightly. In fact, it’s been shown that bad mentoring can actually be worse than no mentoring at all. 

Here are some questions to help you get to know your mentee and how to better guide them:

  • What are your goals for this relationship?
  • Where do you see yourself in 3-5 years?
  • What are your greatest challenges right now?
  • What part of your job most excites you?
  • What motivates you?
  • If someone was writing the story of your career, what would you want it to be?

Questions mentors should ask their mentees to help get to know them and how to guide them throughout the relationship
Questions mentors should ask their mentees to help get to know them and how to guide them throughout the relationship.


If you’re looking for even more ideas, check out Soapbox’s list of 121 one-on-one meeting questions

Maintaining a strong relationship with your mentor

Maintaining a strong relationship with your mentor can be invaluable to your career. Whether to stand in your corner, provide advice or bounce ideas off of, having a mentor can play a significant role in your life — both professional and personal. 

Ideally, the relationship between mentor and mentee doesn’t end after a handful of meetings — rather, it’s one that lasts. 

There are a number of things you can do to ensure that your relationship doesn’t fizzle. 

  • Decide on your meeting cadence: Discuss how often you want to check in with each other and in what format. Maybe you meet once a month but check in every couple of weeks via email or slack. Find a cadence and routine that works for both parties.
  • Follow-through: It’s easy to cover a lot of ground in your mentorship meeting, but not follow through. The accountability goes both ways: Your mentor can hold you accountable to reaching your goals and you can hold your mentor accountable to meeting regularly and following through on commitments made.

Above all, be authentic. Mentorship, at its core, is about building a relationship. Like all good relationships, there should be mutual respect, good communication and empathy. Don’t let the relationship die once you’ve reached your goals. For a successful mentorship program, invest in the long-term!


Nicole Kahansky is the Content Marketing Manager at Hyper Context, a meeting software that empowers over 100,000 managers and their teams to be high-performing by combining quarterly priorities, weekly meetings, and engagement measures, all in one place.

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