Questions to Ask a Mentor: 40 Prompts To Get the Most From Mentorship

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Sara Cravatts
Sara Cravatts



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.

great questions to ask a mentor

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. 

The simplest way to extract knowledge from your mentor is to ask questions, and we’ve rounded up 40 — some from experienced entrepreneurs who have gone through the process themselves — to get you started.

This article will discuss:

  • How to prepare for a meeting with your mentor
  • Questions to ask a mentor in your first meeting
  • Questions to ask a mentor about careers
  • Questions to ask a mentor about leadership 
  • Questions to ask a mentor about work-life balance

Great questions to ask a mentor

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. 

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.  

Questions to ask a mentor in 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?

Questions to ask a mentor about careers

Many times, the reason you sought out mentorship is because you want career advice and guidance. You don’t have to reinvent the wheel when asking your mentor questions, but you should tailor your inquiries to be relevant to the career you have — or want to have. 

Some helpful career questions to get you 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?

Questions to ask a mentor about leadership

When choosing a mentor, it’s important to look for someone who possesses strong leadership skills. Leading is a difficult craft, and having a mentor who has mastered it 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 about work-life balance  

As you climb the career ladder, it’s important to maintain a healthy work-life balance. Your mentor (hopefully) has already mastered this art, and can offer tips and tricks that help ensure you are 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?

One last tip: Mentorship isn’t a one-way street. 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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