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20 Questions To Ask A Mentor About Leadership

If you want to take your career to the next level, here are 20 questions to ask a mentor about leadership will help you figure out next steps.

Is it time to take that next step in your career? Do you want to take your current role to the next step? Are you thinking about taking your professional career to a whole new level?

Don’t stress, it is yours to take. It’s natural to feel nervous and want to back out, but you’ve got this! You just need a little help and encouragement from a mentor.

Why it’s important to have a mentor

A mentor/mentee relationship is an important one to develop in your twenties. Mentors have a wealth of knowledge and they are ready to share it. They’ll also act as a sounding board for your professional development and career advancement.

A great mentor will push you to be your best and celebrate all you accomplish. There are many reasons why it’s important to have a mentor, here are a few of those reasons.

woman in a coffee shop

Advice from someone who’s been there 

Ideally the right mentor will have similar life or career experiences that you are going through currently. Because of this you’re able to get advice from someone that has a perspective from the other side. They can help you see through any blind spots in your career development and help you meet your career goals.

Mentors have connections 

The more people you know, the more you are connected to. Having a good mentor with connections comes especially in handy when you are looking for a new job or changing careers. New career prospects often come with networking!

Get insight to strengths and weaknesses 

Having a mentor give constructive criticism and valuable feedback is one of the best benefits of this type of professional relationship. Think about how much more prepared you’ll be for job interviews, or performance reviews.

Who can be a Mentor

The Muse suggests that a mentor should be a person that can play an active part in your life. As much as I’d like to say that Taylor Swift and Jenna Kutcher are my mentors, that’s just not the case.

Even though I’ve learned a lot from them both, I don’t personally know Taylor or Jenna. Which means I can’t actually have conversations with them. 

The good news is that finding a mentor can be an easy process. Take a look at the people already in your life. Do they have the qualities you want in a mentor? A mentor can be a…

  • Friend
  • Former professor 
  • Former boss
  • Career coach 
  • Neighbor 
  • Mentorship program

Once you have your mentor, you can start asking them good questions. Which leads us to the topic of this post. 

Why Ask A Mentor About Leadership

There are several reasons why you may want to ask your mentor about leadership. It makes for great conversation and learning opportunities. It can be a good starting point to better understand specific interests of roles that you want to explore.

It’s also a way to learn more about your mentor’s background and qualifications. You can build your mentor-mentee relationship while learning about their experiences in the business world. There are some other work scenarios that may prompt you to ask specific questions about leadership. 

Maybe you’re up for a promotion at work that would put you in a leadership role. You could also want to show initiative by showing more of your leadership skills. Honestly, gaining insight about a new skill is always a great idea.

Questions To Ask A Mentor About Leadership

20 Questions To Ask A Mentor About Leadership

Here is a list of questions to ask your mentor next time you have a mentorship meeting with them. These will help to get the conversation about leadership going. If you have any others that I didn’t list, add them in the comments down below. 

1. What qualities make a great leader?

This is great to ask so that you can see where you stand, and what you maybe should work on.

2. What is your experience with leadership?

Learning about your mentor’s background is essential for a great mentorship relationship. This could be a great conversation starter about the topic. Also ask them what is the most important leadership lesson they’ve learned.

3. Why is it important to have great leadership skills?

It’s always good to get perspective on how important leadership is to others.

4. What’s the best piece of advice on leadership that someone has given you?

I love this question because it’s passing down wisdom. I’d pay special attention to this answer.

5. How did you implement that advice?

This is a great way to go deeper with the previous question. 

6. How will I know when I’m ready to step up into a position of leadership?

If you are unsure about your first steps then the advice from this question can be very affirming for you.

7. What is your biggest challenge about being a leader?

When it comes to challenges, it’s great practice to anticipate them whenever possible. Asking this question will help you do that.

office meeting

8. What do you love most about being a leader?

Here is another question that will allow your mentor to share a little more about herself/himself. 

9. How do you handle negative feedback from your team or coworkers as a leader?

If you’re like me, negative feedback can sometimes be hard to hear. I imagine it’s much harder from a leader’s perspective. It’s great practice to get advice about situations like this.

10. What do you think my strengths are when it comes to leadership?

It’s always nice to hear what you do well. This is valuable insight for when you get asked this question in interviews and any other professional meetings.

11. What about my weaknesses?

Again this is valuable information for things like interviews. Knowing your weaknesses also gives you a chance to work on them. Your mentor can guide you in building new skills.

12. What can I do to better equip myself to be ready when a position of leadership opens up?

If you’re ready to take the next step in your own career it’s good to create an action plan. Your mentor can help you do this by giving you a starting point. Then encouraging you throughout the way. Additionally, you can get your Performance Management Certificate, which can provide the necessary tools and knowledge to excel in a leadership role, further preparing you for future opportunities.

13. What are some best practices for connecting with your team?

Team building is a big part of leadership. It’s great to get advice on this subject as well as building strong relationships.

14. How do you determine your leadership style?

If you need help determining what kind of leader you’ll be, leadership styles is a great topic to bring up.

15. What’s the best way to motivate a team?

Here’s another practical question about team building. The tips you learn here you’ll definitely want to hold on to.

16. What are some obstacles that you had to overcome in your leadership position?

I think one of the most valuable aspects of having a mentor is the personal stories you hear. The answer to this question would make a great learning opportunity.

17. How do you make each person feel valuable as an individual and as part of a team?

A great leader can make each team member feel seen and heard. Asking your mentor this question will give you great insight into how to do that.

18. How do you smoothly transition from being a small part of a team to the leader of a team?

The transition between positions isn’t talked about enough. So talk about it, you’ll be glad you did.

19. Do you have any leaders that you follow and/or look up to for inspiration?

It’s always nice to know where your mentor goes for inspiration. You may discover your new favorite leader to follow as well.

Questions To Ask A Mentor About Leadership

20. What books, podcasts, and other resources would you recommend that I look into?

Even though you’re out of school, or maybe will soon be out, the learning doesn’t stop. Your mentor will be able to guide you to places to further your education and sharpen your leadership skills.

Asking the right questions can be hard. Skip the small talk and practice your soft skills!

If you’re feeling unsure of what you specifically want to know, make a list of mentor questions that include different types of questions.

You can ask about a specific situation, ask for advice for some of your biggest challenges, or questions about strategic planning for a career transition down the line.

In return, your mentor should also be asking you the hard questions to help you gain valuable insights and so that they can give you the best advice.

Final Thoughts on Questions To Ask A Mentor About Leadership

To close out this post I wanted to drive home the importance of having a mentor. Especially in situations like this. Taking the next step in your career can be intimidating and scary, but it doesn’t have to be.

Having a mentor helps because they’ve been there before. They know what you’re going through. 

More resources about mentorship:

5 Benefits of a Mentor

33 Famous Mentor Quotes

50 First Mentor Meeting Questions

5 Questions to Tell if Your Mentor is a Good Fit For You

We’ve also got some leadership advice from various GenTwenty contributors.

How To Elevate Your Leadership Skills

5 Leadership Podcasts To Listen To Today

5 Leadership Qualities That Make You a Good Leader

Inclusion Matters: How to Be Inclusive as a Leader

4 Creative Skills to Learn to Grow Your Career

About the Author

Kelly Clark

Kelly graduated from Liberty University with a degree in Advertising and Public Relations and a minor in Journalism. Even though it took her a little while to find her career path, she was always meant to be in Communications. She remembers writing poems and songs when she was a little girl and pitching to my parents the reasons why I should have a cell phone when I was a teenager. She currently has a blog ( where she talks about her weight-loss journey, mental health and personal development. Her hope is to encourage and inspire readers and let them know they are not alone. Reading blog posts like that are what helped her in tough times and she wants to pay it forward. She loves dance fitness, listening to music, and creating layouts in her bullet journal. She's a big fan of planning, especially when cute notebooks and pens are involved. Her dream job has changed so much over the years; right now she'd love to co-own a dance studio.