Tips for mentors

27 Questions mentors should ask their mentees

As a mentor what questions should you ask your mentee? Here are 27 thought-provoking questions to build a meaningful mentoring relationship that leads to growth. Let's break the ice and go deep to unlock growth.

Ryan Carruthers

December 14, 2021

Knowing what to ask your mentee can make or break the relationship. In order to not waste your time or theirs, we’ve compiled a list of 27 thought-provoking questions the mentors should ask their mentees. 

How do we know these questions are good? 

At Together, we power mentoring programs at companies large and small. We’ve seen hundreds of mentoring relationships, so we know a thing or two about building a successful mentoring relationship

Now let’s pause. 

  • If you’re a mentor, the questions below are a great starting point to get to know your mentee and unpack their goals and barriers.
  • If you’re planning a mentoring program, pair this article with our resource on mentoring session agendas. You’ll find more questions and different ways to structure your mentoring program. 

Ready to take your mentoring relationship to the next level? Let’s dive in!

Meeting templates for mentors and mentees
Focused mentoring sessions start with clear agendas. We've packaged together 5 of the best mentor meeting templates to help you break the ice and kick-start meaningful discussions.


What is the role of a mentor?

It's incredibly fulfilling to be a mentor. And don’t think that you don’t have enough time to be a mentor. A Fast Company article cites a study saying,

“we tend to perceive that we have more time when we’re making meaningful contributions.”

Therefore, both you and your mentee stand to benefit. A mentor plays a valuable role in the life of a mentee.

Let's look at the role and impact of great mentors:

Provide guidance and advice

Mentees look up to their mentors. Often, you are in a position they’d like to be in someday. You hold valuable information that can help them attain their goals. Offer them advice and guidance during sessions to help them chart a plan from where they are to where they want to be. 

Give empathetic and honest feedback

You won’t benefit your mentee unless you can give them honest feedback. However, some situations will call for you to be empathetic in the delivery of that feedback. That doesn’t mean you should hold back the truth. Your mentee will grow from being able to see their weaknesses. Likewise, they’ll appreciate straight talk that helps them grow despite it being challenging to hear. 

Challenge mentees to grow and hold them accountable

Encourage your mentees to take on challenges, even ones they may feel are too large for them to tackle. Help them get out of their comfort zone. And follow up with the challenges you give them. Your mentee needs you to call them to account for their growth and reach the goals they’ve set. We all need people to help us when we’re feeling stuck. You have the unique opportunity to be that for your mentee. 

Ask great questions

We can often learn more when we have to think for ourselves. That’s why the questions you ask your mentee should challenge them and guide them. The answers they offer will reveal more about themselves but can also help them recognize growth opportunities. 

Related: 29 Questions mentees should ask their mentors


What questions to ask your mentee

Asking your mentee thought-provoking questions is vital to the learning process for both of you. It can help you gain insight into their background, goals, and ways of thinking.  But questions can also be used to help your mentees see truths about themselves, such as their strengths and weaknesses. You can also encourage them to find their own answers to a challenge if you know the right questions to ask. Here are some questions to help get you started. 

Ask them about their career journey

Find out more about your mentee and their work experience by asking them about it. But you need to use specific questions rather than a general “tell me about your career so far” type of question. 

While it is a good idea to have some questions prepared, don’t feel you need to stick to a script. Remember, when you ask questions based on the information your mentee has already offered, it demonstrates your interest in them. 

Here are some questions you may want to ask. 

  • What was your educational experience like?
  • What was your first job?
  • What led you to your current career path?
  • Did you plan to have this career path, or did it happen organically?

Get to know them as a person

You don’t need to be too personal, but asking questions can help you get to know them as a person. The right questions can lead you to find out more about your mentee to help better understand who they are and what’s important to them. 

Consider some of these suggestions or develop questions of your own. 

  • Where did you learn your current values?
  • Do you have any role models you look up to or people you admire?
  • What do you love to do outside of work?
  • What inspires you?

Understand their goals

A crucial part of mentoring in the workplace is to help mentees define and reach goals. To help them be successful is one of your roles as a mentor. So, you’ll want to have a good understanding of what their goals are. 

Sometimes a mentee won’t have a list of goals, and you’ll need to help them define their goals for the mentorship. 

Here are some questions to help you and your mentee do this. 

  • What are your short-term goals?
  • What are your long-term goals?
  • What interested you about having a mentor?
  • What areas of your life do you want to grow in?
  • What skills do you want to develop?
  • If you could go back in time, would you choose a different career?

Identify their strengths and weaknesses

To be an effective mentor, you’ll need to have a strong understanding of the strengths and weaknesses of your mentee. Sometimes, it can help to know how the mentee sees themselves. With the right questions, you can help them think deeper about their strengths or things that hold them back. 

  • What do you consider to be your strengths?
  • In what areas do you think you need to improve?
  • Does your current role help you leverage your strengths?
  • What parts of your job do your weaknesses hinder you?
  • How do you mitigate your weaknesses?

Help them work through a challenge

Not every mentee wants to develop their skills or has a goal in mind. Sometimes, they’ll need you to help them work out a challenge. Your advice and coaching can be essential to help them overcome whatever is holding them back. 

Here are some questions you can use to help define the challenge for your mentee. 

  • What’s a challenge you’re currently facing in your career?
  • What ideas have you developed to help you overcome challenges and meet your goals?
  • What obstacles do you see that might prevent you from achieving your goals? 
  • What will you do differently tomorrow to meet those challenges?
  • How can I support you in overcoming your challenges?

Help them reflect and express gratitude

Thankfulness is a vital life skill. It can help us focus on the good things we have rather than on all the things we feel we are lacking. Encourage your mentee to have an attitude of gratitude by asking them some of these questions. 

  • What are you most grateful for?
  • Who is someone that you’re grateful for in your life? What have they given you?
  • What was a period in your life or career where you felt like you had the most growth?

Build a strong relationship with your mentee

The key to a great mentorship experience is connection. Each mentorship will be different. It often depends on the goals and objectives of a mentoring program. But there are things you can do to build a successful mentoring relationship. By asking the right questions, you can show your mentee that you genuinely care and are interested in them and their growth. That is one of the key ingredients in developing a strong connection. 

Starting a mentorship program? You’ll want to check out our guide that breaks down the whole process into six steps. Likewise, running a mentorship program at scale in your workplace can be an administrative nightmare. Mentoring software, however, makes it easy to pair the right employees together for career-changing development. Learn more about how our software works.

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Want incredible results from your mentorship program? Then download our comprehensive list of best practices.

We draw these best practices from the first-hand experience of program managers like you and our own expertise. This white paper is a comprehensive guide that will be your roadmap to building a world-class mentoring program.