50 Questions To Ask Your Mentor
These 50 questions are a great way to get you started if your mentor relationship is new. And even if you’ve known your mentor for years, I think you’ll still find a new conversation starter or two!
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50 Questions To Ask Your Mentor

So, you’ve finally found a mentor. Congrats! Now what?

Now, it’s time to start building your relationship and soaking up all that invaluable experience and advice your mentor has to offer. (P.S. If you haven’t found a mentor yet, check out my top tips for finding a mentor and how to start a mentorship program)

Always remember that agreeing to be a mentor is a big commitment and you want to respect their time by being prepared. What does it mean to be prepared? Think of yourself as the owner of the relationship. Take the responsibility of reaching out and scheduling the meetings. Take time to reflect on your goals before the meeting and prepare questions. Ideally, the conversation should feel organic and not like an interview. However, conversation flow might be more difficult in the beginning stages of the relationship. 

These questions are a great way to get you started if your mentor relationship is new. And even if you’ve known your mentor for years, I think you’ll still find a new conversation starter or two!  

Lessons

These questions dive into the lessons your mentor has learned along their career journey that you might be able to apply in your own career.

  • What is something you wish you knew earlier in your career?
  • What is something you learned in your first job that you still apply today?
  • What is the best piece of advice you’ve received?
  • What is the worst piece of advice you’ve received?
  • What was a professional mistake you made and what did you learn from it?
  • How did you know it was time to make a career transition? 
  • Have you ever had to work in an environment where you didn’t feel supported? If so, how did you get through it?
Dive into the lessons your mentor has learned along their career journey that you might be able to apply in your own career

Goals

These questions are centered around goals and goal-setting. Come prepared with your goals (professional or personal, depending on the nature of your relationship) already listed out for discussion. Make sure you also come with an open mind. One benefit from having a mentor is getting another perspective. Your mentor may think your goals are too big or too small for the timeframe. Try to prepare for how you would handle that feedback. 

  • Here are my goals for this mentor/mentee relationship. What are your goals for the relationship?
  • Here are my short-term career goals (short-term goals generally have a 3-6 month timeline), can you please provide feedback?
  • Here are my medium-term career goals (medium-term goals generally have a 1-2 year timeline), can you please provide feedback?
  • Here are my long-term career goals (long-term goals generally have a timeline greater than a few years), can you please provide feedback?
  • What systems do you use to track personal and professional goals?
  • If you feel you are off track for a certain goal, what do you do to get back on track? 
  • What is a recently accomplished goal that you’re proud of?

Leadership

These questions will help you understand what kind of leader your mentor is and help you decide what kind of leader you want to be. Remember that you don’t have to be in a management position to be a leader!

These questions will help you understand what kind of leader your mentor is and help you decide what kind of leader you want to be
  • How would you describe your leadership style? Has it changed over time?
  • What were the hardest lessons to learn when you became a new manager?
  • How do you inspire your team when you aren’t feeling inspired yourself?
  • What character traits do you most attribute to your success?
  • What character traits do you look for in your team?
  • What character traits do you look for in a potential boss?
  • At what point in your career did you feel comfortable saying ‘no’?
  • How do you work to connect with colleagues in different generations?
  • How do you work to promote diversity in your workplace?
  • How do you know when to ask for help?

Networking

Some people hate networking, some people love networking. Regardless of your feelings, it’s something we should all do to further our careers. Your mentor can be a great resource for expanding your network. 

  • Is there anyone in your network that you think I should meet?
  • What is your favorite way to network?
  • What is a recent networking event you attended or an upcoming networking event you plan to attend?
  • Are you part of any professional networks?
  • Are you part of any philanthropic organizations?
  • How do you balance doing traditional office work with networking and interacting with other leaders in your organization? 
  • Do you have any tips for someone new to networking?

Personal

Some of these questions are personal for your mentor and some of them might be personal for you. Use your judgement to gauge how forthcoming your mentor is willing to be. A good way to test this is to share something personal of your own and see if they share in return. Maybe you end up saving some of these for later on in the relationship, and that’s ok. And, of course, only ask about relationships and/or children if they have already mentioned them to you.

  • How to manage two demanding careers (you and your spouse)?
  • What was most difficult about becoming a working mom?
  • What has surprised you the most about becoming a working mom?
  • How to address inappropriate comments from someone who means well?
  • How to address inappropriate comments from someone senior to you?
  • Who has had the biggest impact on your career so far, positive or negative?
  • What originally sparked your interest in your chosen field?
  • How do you stay inspired?
  • What does self-care mean to you and how do you practice it?
  • Who is your mentor? 
  • I have encountered a difficult situation at work and I have a few potential solutions, could you help me brainstorm a path forward?
Some of these questions are personal for your mentor and some of them might be personal for you

Reading (and other media)

From my experience, a lot of successful people are big readers, so asking about their reading list or media consumption can be a great conversation starter. Of course, be prepared to discuss your own latest reads, too. I would suggest making an effort to actually read one of the books you discuss. Then, you can have a conversation about it in your next meet-up!

  • What do you read to keep up with developments in your field?
  • What was the last book you read?
  • Do you listen to podcasts? If so, what is the last podcast you listened to?
  • How do you prefer to consume news and other media (i.e., TV, internet, radio, physical newspaper, etc.)?

Not Work Related

Not every question has to be so serious! Discussing things beside work can help you build a genuine relationship with your mentor.

  • Ask about family or friends.
  • What are your hobbies outside of work? 
  • Discuss a recent trip or upcoming trip.
  • What do you read or watch for fun?

I hope you found a few questions for the next meeting with your mentor!

My personal favorites from this list are: 

  • What is the worst piece of advice you’ve received? 
  • How do you inspire your team when you aren’t feeling inspired yourself?
  • Is there anyone in your network that you think I should meet?
  • What was the last book you read?