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22 questions to ask a mentor for a great mentorship experience
Oct. 2, 2020
Knowing how to ask good questions to a mentor is key to a successful relationship. At MentorCruise, our mentees often wonder about how to ask the right questions that will lead to meaningful exchanges between the mentee and mentor.
After all, there are so many questions, but not enough time to ask them all during mentoring sessions. Whether they’re on topics related to career paths, job search, how to ace job interviews, leadership lessons and so on, asking the right questions to your mentor is more of a skill that you can improve upon with the right tips.
As a mentorship platform, we’ve hosted so many successful mentorships. Many of them partly attribute their success to asking the right questions. As such, we’ve decided to put all their key learnings on how to ask the right questions into a guide.
You’ll learn:
Tips on how to ask good questions to your mentor
22 good questions to ask a mentor
4 tips on how to ask the right questions to a mentor
1. Ask clear, specific questions instead of vague ones
In your mentoring questions, good questions to ask your mentor are those that are clear and relevant to the mentor’s expertise. Normally when people look for a mentor, they’re looking for guidance to solve a specific issue in their career.
Figure this, you’ve decided to get a mentor, so that you can earn how to become a better leader. You get into the topic of public speaking because it’s been a lingering issue of yours.
Here are two examples that roughly ask the same question, but one is more specific and the other a bit vaguer:
A: “How do I become better at public speaking?”
B: “What do you do to avoid nervousness when speaking in public?”
A is an example of a bad question to ask if you want meaningful advice precisely because it’s too vague. Why is it not appropriate for a short mentoring session? Because it’s a public speaking question that requires a deep answer to be effective.
On the other end, B asks a more specific question on nervousness when speaking in public. The mentor can give more actionable advice on this because it’s more specific.
2. Ask questions on these key topics to get the ball rolling
Ask questions on these topics to get to know the mentor better and initiate a good conversation:
Expertise, career development, self-improvement and building skills. You can ask specific advice on how to learn and develop a skill or for actionable tactics to help surmount a certain obstacle.
Stories. Storytelling is a craft that humans naturally gravitate to as social creatures. Relationships develop through sharing stories that help us connect with one another. This principle also applies to mentoring relationships. For example, if you have a startup mentor, you can ask this story on risk-taking: “What was that one time you took a huge risk and it paid off?” This question can give important insights and will help the mentor become more open with their feelings by telling you their personal stories.
Situational. Ask more specific issues regarding your career or theirs. Here’s a sample question on leadership lessons: “My boss told me to take ownership of my managerial tasks. What does that mean?” Here’s a question that most experienced managers will know how to answer, but may still initially confuse newer ones. If your mentor is much more senior than you and has been in a position of influence, they will know how to answer this.
Accountability. From time to time, it’s important to circle back and to make sure that you’re correctly following your mentor’s advice. Ask questions on how to improve your rapport or if you’ve been making good progress throughout this mentorship.
3. Avoid asking rhetorical questions and keep small talk to a minimum
Don’t force a conversation. Your first session will always be the most awkward one. You and your mentor have just met each other for the first time, so you will still need to figure out how to go about this interaction.
Instead, ask the types of questions highlighted in the second tip and be very specific in the way that you’re asking them. More often than not, these tips improve the quality of your conversations and allow you to develop deeper mentoring bonds.
In the worst-case scenario, MentorCruise allows you to have a 7-day free trial for first-time mentorship sessions. You can end the relationship when you’re not feeling a connection between the mentor and yourself.
4. Be prepared
The worst thing that you do in your mentoring sessions is to come in unprepared, with no specific questions to ask your mentor on. This mentorship has been built based on your desire for self-improvement. If you don’t want to achieve your goals, then there’s no point in continuing this mentorship.
Mentorship is an investment in time and energy. Being unprepared implies that you’re not interested enough to make this mentorship work. And in return, your mentor might grow to care less about your progress. After all, a great mentoring relationship is partly predicated on a mentor who wants to see you succeed, so you have to put in the hard work.
22 questions to ask a mentor
Here are boilerplate questions to consider asking a mentor during your sessions. Don’t forget to create your own twist for each question.
Remember that mentorships thrive when mentees ask specific questions, instead of vague ones. These are meant to be open-ended questions that you can turn them into something more specific.
And one more thing: context is key. Contextualize your questions before or after asking. This helps the mentor figure out how to give meaningful answers.
Expertise, self-improvement and building skills
Where do you think my strengths lie in?
How can I develop the right amount of discipline to achieve my goals in this industry?
What are the necessary skills that I should develop to rapidly grow in my career?
What are some things in your career that you regret not having done earlier?
How do I effectively manage my time and prioritize accordingly?
Do you even get impostor syndrome? How did you learn to get over it?
Did you have a hard time starting out in this industry?
What are some hard choices that you made to get where you are in your career?
Did you experience some major setbacks in your business/career path? How did you bounce back?
What are some instances that you would have done differently?
How do I handle this situation better?
Do you have some tips for networking online?
This question is even more relevant than ever today, as more companies are embracing working from home.
I feel stuck. What are some ways that I can apply to solve this issue?
My boss and colleagues are treating me unfairly. Based on your experience, do you think I should move elsewhere?
I have an interview coming up. What are some interview questions and other things that I need to know about to nail it?
Do you have any tips on how to improve my resumé for my job search?
How do I prepare myself for performance reviews?
What would you like to see me do every week to show that I’m improving throughout this mentorship?
Am I progressing in the right direction?
Am I correctly listening to your advice?
Are there any other topics you’d like for us to discuss?
Do you have any feedback on how we can improve our mentoring rapport?
Join MentorCruise to find the right mentor for your professional needs
In this guide, you’ve learned how to ask the right types of questions in your mentoring sessions and questions to consider asking.
Remember that asking the right questions to your prospective mentor is only one part of the equation. You also already need to learn how to choose the right mentor to help you achieve your goals and get the career advice that’s right for you.
The road to career success is often a bumpy one, and career development may often seem confusing. But imagine how much easier it would be if you had an experienced industry leader available anytime to offer career advice and expert guidance. At MentorCruise, you can pick through many experts and industry leaders to see the right mentor for your needs.

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