10 Questions to Ask Your Mentor

Written by
Laura Francis

How to Connect with Your Mentor

Mentoring software has made it easier than ever to find a mentor. The organizations that we work with here at River typically launch a mentoring program with a goal in mind, such as tying the program to leadership development or diversity and inclusion initiatives. The great part about River is that it makes the matching process much faster for administrators and users, regardless of what the program focuses on or how many people are involved. But what happens once a name pops up that River’s intelligent matching algorithm suggests is a good fit for you?

Well, that’s when the magic happens! Mentoring should always be about the humans who are connecting, even when that connection happens via software. So, with that in mind, here are 10 questions you can ask your mentor to help you get to know them and begin building a relationship with them.

1. Have you mentored anyone else before?

This question will help you assess the person’s experience as a mentor and can lead to a conversation that digs into their views on mentoring, what role the mentor should play, what they expect of you as a mentee, etc. This type of understanding is a key part of building a solid relationship with your mentor.

2. What made you want to be a mentor?

This is a great question to ask someone, because it gets to the heart of their motivations. Were they nominated or otherwise asked to be a mentor by someone else because of their role/experience? Do they want to give back to those around them because they empathize with people and recall what it was like to need a helping hand? There could be multiple reasons why someone agreed to be a mentor; understanding why can help you better understand what to expect.

3. Are you interested in helping me with [state whatever your mentoring goal is]?

If the person is not able or willing to help you with your mentoring goal, then they likely aren’t going to be a good mentor for you. Knowing this up front is crucial to having a successful relationship. If you clicked on a personal level but they can’t help you with your goal, you can always adjust your goal for this relationship and go find a different mentor for the original goal you stated. No one ever said you should only have one mentor!

4. Tell me a little bit about your experience with [state your goal/mentoring topic area here].

Mentoring Conversation

Is the mentor a relative newbie in the area on which you want to focus your relationship? Or are they a master practitioner with years of experience? While many people may think they must have the master expert as their mentor, you may find that a relative newbie is a good fit for you if you are also just starting to learn about a topic yourself. You want to find someone who can recall what it was like to be in your shoes and who can help you trek along your learning path. And consider this: If they walked that path recently, they may provide some good advice that the expert has forgotten.

5. What was your biggest a-ha moment when you were learning about [state your goal/mentoring topic area here]?

This question allows you to discover what excited this person about the topic at hand and what their learning journey was like. Their a-ha moment may also be a great learning moment for you and become a great point at which you and your mentor can start a profound conversation.

6. What obstacles have you overcome to get where you are today?

You will get to learn about your mentor and their life journey with a question like this. It can reveal what areas they found challenging in their work (and possibly in their life in general), and it can create a wonderful opportunity for you both to open up to one another about yourselves. Be brave in mentoring!

7. How do you prefer to meet? Face-to-face? Phone? Video chat? Email? Text?

Mentoring Conversations webinar

While not as exciting in a getting-to-know-you sense, this question can be one of the most important ones to ask that too many people overlook. If you don’t agree on how you want to communicate, then the relationship itself could be in trouble right from the start. Poor communication is one of the biggest downfalls of mentoring relationships. Reaching agreement on how you will communicate will go a long way toward ensuring the success of your relationship.

8. Are you able to meet with me at least once a month to work on this?

This question helps you ensure that your mentor has the time for mentoring and allows you to set expectations with one another regarding the time commitment aspect of mentoring. While scheduling conflicts do come up, it is important to talk with one another right away about what you expect to need from one another regarding time for this relationship so that no one is frustrated or disappointed by the actualities of the relationship. (And while I state “at least once a month,” you should restate this with whatever time commitment you need.)

9. How can we hold one another accountable?

This is a great question for a mentor (or mentee!) because it helps you both think about the relationship and how you want to show up or be present to one another. It also makes it clear that this is a partnership where equality should be asserted. If one of you is not holding up your end of the bargain, the other needs to know that they can and should hold you accountable.

10. Are there any areas that you need to be off limits?

Blend mentoring with training

This last question can be a good one to ask so that you can assess if the topic that you want to learn about encroaches on the area that the mentor needs to keep off limits. It’s better to know that before your start asking questions and getting frustrated with the mentor for not answering.

These 10 questions can get you started with learning more about your mentor, but you should use them as a starting point, not the endgame. Engage in open conversations with the mentor and see where that takes you. A mentoring relationship is like a living ecosystem: it will evolve over time and you should be actively involved in crafting its evolution to ensure it continues to meet your needs.

Related Resources

The Mentoring Journey

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The Career Beacon: Guiding Professional Goals with Mentorship

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