49 Questions To Ask a Mentor

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Bailey Maybray
Bailey Maybray

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Whether you’re just starting out in your career or you’re nearing the top of the corporate ladder, finding a mentor can be a powerful tool to help you reach your goals. And in that first chat, you want to come prepared with strong, interesting questions to ask a mentor to set yourself up for success.

Questions To Ask a Mentor: a man and a woman face each other with questions marks in the middle.

According to a survey of 8k workers, 9 out of 10 employees who have a mentor report being satisfied with their jobs. For those who didn’t have mentors, more than 4 in 10 workers say they’ve considered quitting their jobs in the three months prior to the survey.

If you’re lucky enough to find a mentor who is willing to offer their guidance and expertise, put in the work to make sure you’re getting the most out of the relationship.

Table of contents:

How to prepare for a meeting with your mentor

You shouldn’t wing it for your first get-together with your mentor — if they’re taking time out of their day to meet with you, make the best use of this opportunity and come as prepared as possible.

If you don’t already work closely with your new mentor, familiarize yourself with their career path (their LinkedIn profile is a good starting point), accomplishments, and skills. You can make note of the following, for example:

  • Prior work experience: What about their professional journey is interesting or relevant to yours?
  • Featured projects: Does any of their featured work or projects impress or intrigue you?
  • Skills: Do you have any questions about how this person learned certain skills?
  • Posts: Have they posted anything recently that resonates with you?

Next, identify what you’re hoping to get out of the relationship. Do you want to enter the industry your mentor is currently in? Are you looking to one day climb the ranks to their position at your company? Are you not sure what you want from your career and need some guidance?

Understanding what you need will help your mentor help you. Once you’ve researched your mentor and clarified what your goals are, come up with a list of preliminary questions.

When asking questions, especially in a virtual setting, remember to speak with enthusiasm. You can try out the following tactics to demonstrate your excitement and interest in your mentor:

  • Speak louder than normal
  • Change your intonation by raising and lowering your voice
  • Maintain eye contact, either by looking at their eyes in person or directly at the camera
  • Nod to show active listening
  • Engage with their responses, asking follow-up questions and offering your own comments
  • Keep your posture up

End the conversation with excitement, thanking them for their time and asking to set up another meeting in the future.

Good Questions To Ask a Mentor

Good Questions To Ask a Mentor: a set of questions to ask your mentor at your first meeting and about work-life balance.

At Your First Meeting

During your first chat with your mentor, you want to establish a rapport and learn more about them.

Start by engaging with them on how they’re doing, providing more than just “good” or “great” in response. Offer responses that create a natural transition into questions, such as:

  • “I’m doing great — I’ve been looking forward to meeting with you since we first connected!”
  • “I’m good, the weather is beautiful today. You’re based here as well, right?”
  • “I’m feeling relaxed, my team just finished a big project.”

These responses start the conversation on a positive note, and gives your mentor an opportunity to ask follow-up questions about your day, project, or work. Afterward, you can start asking typical first-day questions.

Consider asking some of the following questions for your first meeting:

  • How did you learn X skill? (For example, how did you learn public speaking?)
  • Do you have a mentor? If so, who is it and what have they taught you?
  • What is something you wish you had known when you were at my career stage?
  • What is something you regret spending time doing? — Denise Schaefer, co-founder of Surge
  • What is the biggest mistake you’ve made in your career?
  • When you made a mistake and wanted to give up, what did you do to keep going? — Samorn Selim, CEO of Career Unicorns
  • What is the biggest obstacle you’ve had to overcome?
  • What are your favorite book, podcast, or video recommendations for career growth and inspiration?
  • What practices do you have in your personal life that help your professional life?
  • How do you stay inspired?

About Work-Life Balance

Climbing the career ladder means figuring out what a healthy work-life balance means for you. Ideally, your mentor has mastered this art, and can offer tips and tricks that help ensure you stay fulfilled inside and outside of the office.

Some thoughtful questions worth asking:

  • How do you maintain work-life balance while still progressing in your career?
  • How did you work on your mental wellness through the ups and downs? — Samorn Selim
  • What is something you do every week that helps you achieve/or come close to a great work-life balance?  — Mark Convery
  • What does work-life balance mean for you? — Melissa Kwan
  • What are some habits you’ve implemented in your personal life to achieve a better work-life balance?
  • How do you know when your work-life balance is off-kilter?
  • What’s your trick for work optimization while maintaining a healthy work-life balance? — Denise Schaefer
  • What if you find yourself in a job where work-life balance doesn’t seem possible?
  • How can you defend your work-life balance if your boss or manager contacts you outside of working hours?
  • Are there times in your career where you’ve sacrificed work-life balance to achieve a specific goal?

Strategic Questions To Ask a Mentor

Strategic Questions To Ask a Mentor: questions about careers and about leadership you can ask a mentor.

Besides more general inquiries, ask strategic questions about their career and leadership experience. You can use their answers to help your own professional trajectory, incorporating their tips into how you handle leadership and your career.

About Careers

Often, you seek out a mentor to get career advice and guidance. Try to tailor your inquiries to both your career and theirs. Consider asking some of the following to get started:

  • Are you assertive or passive in the workplace? What are the strengths and weaknesses of both approaches?
  • How do you earn the respect of your colleagues?
  • How would you choose between doing something that makes you happy and something that makes you a lot of money if it’s one or the other? — Melissa Kwan, co-founder and CEO of eWebinar
  • How did you know you were in the right career?
  • What has been the most constant re-enforcer along the way that you’re on the right track? — Denise Schaefer
  • How far ahead do you think in terms of your career at any given time?
  • What attributes do you think are most important to move ahead in the workplace?
  • What is your North Star when making career decisions? — Samorn Selim
  • What was a pinnacle lesson you learned that helped catapult your expertise in your business or in your career? — Mark Convery, CEO and co-founder of CoCo Vodka
  • What factors should you consider when deciding if a job is right for you?

About Leadership

Try to find a mentor who possesses strong leadership skills. As you progress in your career, you will likely find yourself taking on more managerial responsibilities. Having a mentor who has mastered leadership can give you insights into how to become a better boss.

To learn what makes a leader effective, ask your mentor questions that span all aspects of leadership. Some sample questions include:

  • What interpersonal skills have you developed in order to effectively lead?
  • What do you do before or after work that allows you to be a focused, driven leader when you are around your team? — Mark Convery
  • How did you learn what your leadership style is? — Samorn Selim
  • How can you assert yourself as a leader early on in your career?
  • How can you lead as an individual contributor before you become a manager?
  • How do you ask your team for feedback as a leader and how do you implement it? — Denise Schaefer
  • What do you do if you receive negative feedback from the people you manage?
  • What is the most uncommon trait that the best leaders have? — Melissa Kwan
  • How do you communicate with your peers and direct reports?
  • How can leaders be transparent with their teams without oversharing?

Questions To Ask a Mentor at Work

Questions To Ask a Mentor at Work: a set of questions you can ask a workplace mentor.

Your workplace might assign a mentor when you first start — 84% of Fortune 500 companies offer mentorship programs. Unlike external mentors, you can tailor your questions to your mentor’s experience and trajectory within the company.

A few sample questions to consider:

  • How did you end up joining this company?
  • How does this workplace compare to your previous employers?
  • What did you wish you knew when you first started?
  • What company resources (e.g., learning materials) should I take advantage of?
  • Who else can I meet with in the company for mentorship?
  • What can I do to hit the ground running?
  • How can I best support my team and the organization?
  • Why have you stayed with the company?
  • Where do you see the company going in five years?

Remember: Mentorship benefits both the mentor and the mentee. Reverse mentoring — when junior employees offer guidance to their senior peers — can spur innovation in the workplace and push everyone to succeed. Think of ways you can give back and provide value to your mentor; this can transform a mentor into a long-standing part of your personal network.

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