Tips for mentors

35 Questions mentors should ask their mentees

Wondering what questions you should ask your mentee? This article outlines 27 of them, all of which will help you build a meaningful mentoring relationship that leads to growth.

Ryan Carruthers

Published on 

May 23, 2023

Updated on 

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Knowing where to start with a new mentoring relationship can be challenging. As a mentor, you’re aware of the skills you can offer, but you also need to be able to judge how best to use those skills to help your mentee achieve their goals.

Mentors must learn their mentee's business offerings, challenges, and objectives.

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!


What is a mentor?

A mentor is an experienced and trusted advisor who guides those less skilled than they are (a mentee) to advance in their careers and connects them with opportunities they might not have otherwise had. 

Mentors are responsible for guiding one's professional development, career options, and general areas for life improvement. 

An effective mentoring relationship is valuable for turning a mentee’s vision into reality. Mentors must support and counsel their mentees to assist them in developing successful careers and establishing themselves within an organization.

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


Why should a mentor ask a mentee questions?

The biggest problem mentoring programs and prospective mentors may encounter is not knowing where to begin when building a trustworthy relationship. To assist their mentee at each step of their career journey, from a job interview to a career transition, a prospective mentor can ask their mentee these excellent questions and share their experience.

These mentor-related questions go beyond professional advancement. Knowing your mentee personally is just as vital as understanding their line of work. If you can connect on a deeper level, you'll come up with more creative solutions and overcome all sorts of challenges together.

To assess a mentee’s knowledge and abilities, a mentor can ask their mentee a series of questions. This can aid a mentor in deciding which subject areas they would need to assist their mentee and the best guidance to provide.

To find out how they may offer to advise in more particular ways, such as sending references to businesses in a mentee's desired area or aiding a mentee in finding employment prospects, a mentor can also ask their mentee questions about their professional objectives.

35 Questions a mentor should ask a mentee

Asking your mentee thought-provoking questions is vital to the learning process for both parties. It can help you gain insight into their background, goals, and ways of thinking.

However, questions shouldn't revolve around these areas only. You can also ask questions to help your mentees discover the truths about themselves (including their strengths and weaknesses). 

Finally, asking them the right mentor questions can encourage them to find their own answers to a challenge.

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?

Ask them about Diversity, Equity, Inclusion, and Belonging

Mentees under this category would be women, women who are just returning to work after a long career break, Blacks, people of colour and other underrepresented groups.

Therefore, imply that the mentors asking them these questions are people who have "walked the walk."

Here's for more context: A Black mentee would feel more comfortable answering questions about inclusivity or belonging from a Black mentee unlike if a White mentor asked.

  • Do you feel that you belong at <employer>? Why or why not?
  • Do you feel comfortable being yourself at work?
  • To what extent do you feel that you can disclose your whole identity to your colleagues? Are there aspects of your identity that you feel you need to keep separate from the workplace?
  • Do you mask or downplay any aspect of your physical, cultural, spiritual or emotional self at work? 
  • Do you ever feel left out at work – either when engaging in work activities or socially?
  • Do you feel emotionally and socially supported at work?
  • Have you faced or witnessed prejudice or discrimination in your work setting? Tell me about it.
  • Do you have access to the resources, information and people you need for performance in your role?

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 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?

5 Tips on how to foster a positive mentoring relationship

While thought-provoking questions are an important piece of creating deeper relationships in a mentorship program, mentors should not neglect the other areas of relational building that are key to the success of a mentorship. Even mentors with the best of intentions should continue to evaluate their approach to ensure they are creating the most fruitful environment for their mentees.

Leverage effective communication

Every mentorship is constructed on effective communication. There can be no real connection or profitable discussion without it. In order to truly understand your mentee, help them achieve their goals, and better understand one another, you must have a common grasp of the best way to communicate in your relationship.

Ensure the mentoring relationship is built on trust

Typically, one’s personal growth is connected to their professional growth. Mentoring someone is, therefore, a vulnerable experience, especially for the mentee. Your mentee will not actually share their goals for the future and current struggles if they do not fully trust their mentor. Trying to mentor someone who is holding back will also hold back the progress and results of the program.

Be firm, but don't be harsh

It is important to truly “coach” your mentees - you are supposed to be providing them with advice based on their current predicaments. While this requires you to be firm, you should always communicate your feedback in a way that inspires action and doesn’t discourage them.

Offer helpful and constructive advice

One of the main assets you can provide your mentees is helpful and actionable advice to help them achieve their goals. Providing them with pointers that are too vague or critical to actually give them some direction for their next steps is inherently unhelpful and will not inspire them to succeed.

Work towards helping your mentee achieve their goals

Ultimately, you should focus most of your efforts in mentorship on helping your mentee reach their goals. After unveiling their goals through a solid line of questioning, you can then work through a plan to help them reach their desired destination, providing them with steps they can begin taking immediately. This plan should act as a roadmap for their future until they reach their desired outcome.

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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