man meeting with his female mentor over laptop video call

33 Questions to Ask Your Mentor

Finding a mentor takes a bit of forethought and hard work, but the payoff of that relationship can have a significant positive impact on your career – from quicker advancement and better realization of your career ambitions to guidance and support as you tackle the personal and professional challenges of the workplace. The benefits of mentoring programs are endless.

How to Prepare for a Meeting with Your Mentor

Once you find someone who may be a good fit, take some time to prepare before your meetings, whether they’re your first or subsequent encounters. Although each relationship will progress differently and change organically, establishing goals ahead of your meetings, consistently driving engagement and holding yourself accountable will help you get the most out of your mentoring relationship.

woman writing down questions for her mentor in a notebook

Establish goals

Show your mentor you appreciate their time providing guidance and sharing their knowledge with you by spending some time thinking about what kind of mentoring relationship you want.

First ask yourself why you’re looking for a mentor in the first place. Is it because you’re looking for career guidance in your current role? Or perhaps you’d like to be promoted to manager soon and need help developing your leadership qualities? Or maybe your goals are even more concrete than that: You’d like to develop a skill by a certain date so that you can raise your hand for an opportunity at work.

Whatever it is that you want out of your mentoring relationship, establishing short- and long-term goals will help you determine what you aim to accomplish from your time together. Answering these questions for yourself will help you devise proper questions to ask your mentor in the future.

Drive engagement

You are asking this particular person to be your mentor, meaning they’re probably pretty good at what they do. After all, that’s why you’re asking them to offer their time – and knowledge – to help you grow. It is expected of you to be the driver in this relationship, which includes scheduling your meetings and organizing an agenda for each meeting.

You also need to think about how often you want to meet, and for how long you want to commit to your mentoring relationship. Are you looking to work with this particular person for a few weeks, until perhaps an upcoming annual review or job interview? Or is this a relationship you’d want to maintain for longer?

Once you’ve figured this out, communicate this with your mentor so that you establish reasonable, transparent expectations for your relationship. It is also a good idea to ask them about their preferred communication method. You certainly don’t want to text them over the weekend if they prefer to email on weekdays only.

women mentor meeting with her male mentee in the workplace

Hold yourself accountable

After each meeting, it is a good idea to send bullet points on next steps. Being clear about what you heard and what is expected will help you both be accountable to your promises to each other. Be sure you are setting aside time in between each meeting to complete the tasks you’ve promised so that you can be prepared for the next time you meet. If things arise that will delay your tasks or commitments, simply communicate that with your mentoring partner.


Questions to Ask Your Mentor

Being a mentee has a lot of opportunities, and the key to learning as much as you can is prepping ahead of time and coming to your meetings prepared. Below our mentoring experts have curated lists of questions you can ask your mentor during your time together.


Questions to ask a mentor about their professional experience:

  • What were some challenges you faced in X position?
  • What professional experiences did you have that led you to your current position?
  • What skills have been most beneficial for you?
  • Are there certain things I should be doing so that I can learn skills that will help me prepare for my own career?
  • What career accomplishments – whether it’s working through challenges to earning promotions – are you most proud of?
  • What’s one thing you wish someone had told you when you were at the career stage I am currently?
  • What is the most meaningful part of your job?


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Questions to ask a mentor about their personal experience:

  • How and where do you find inspiration?
  • What values are you committed to? How have they changed since you started your career?
  • What is your biggest fear, and have you overcome it? If so, how? If not, what is stopping you?
  • Why did you decide to be a mentor, and what are your goals for our relationship?/li>
  • What do you enjoy doing during non-work hours? How did you get interested in those activities?
  • What’s on your bucket list?
  • What is your strongest character trait? What is your weakest?
  • What can I do for you in this mentoring relationship?
  • How do you establish work/life harmony?

Questions to ask a mentor about career development and advancement:

  • If you were me, how would you have approached X situation?
  • How should I discuss a potential promotion with my manager?
  • Which leadership skills were the most difficult for you to develop?
  • Where or what do you turn to for continuous learning or skill development?
  • What habits have you found help you to be more productive?


A non-binary person asking their mentor questions about their professional experience

Questions to ask a mentor about navigating an organization:

  • Who are the people I need to align with in this organization to achieve success?
  • How do I become more strategic in my work?
  • When trying to gain buy-in for a new project or program, what is the best way to persuade my colleagues?
  • What should I know about this organization’s structure or culture in order to advance my career?
  • What is something about the culture you helped impact at this org?
  • Who inspires you in the company and why?
  • What is an area of our organization that you would like to learn more about?

Questions to ask a mentor about seeking feedback :

  • Where do you think I can improve that would be most beneficial to the goals that I have shared with you?
  • What could I have done differently in this specific situation that may have improved the outcome?
  • What do you see as my weaknesses? How might I turn them into strengths?
  • How often should I be asking for direct feedback from my manager?
  • What advice would you give me to help me improve my communication?


With the right intention and questions to ask your mentor, you’ll be on a path to a more productive mentoring relationship. This impact will be felt by yourself and your mentor, leading to a more successful outcome for you and your career.

What are some good mentoring topics?

Effective mentoring encompasses a wide range of topics that can help mentees develop personally and professionally. Here are some good mentoring topics to consider:

  • Career Planning and Development
  • Networking and Relationship Building
  • Conflict Resolution and Problem Solving
  • Leadership and Management
  • Emotional Intelligence
  • Time Management and Productivity
  • Workplace Culture and Dynamics

These mentoring topics can be tailored to the specific needs and goals of the mentee, making the mentoring relationship a customized and valuable experience. Explore our expansive list of mentoring topics for mentors and mentees, including skill-related topics, career development topics, leadership topics and discussing topics of diversity and inclusion. The choice of topics should align with the mentee’s objectives and the mentor’s expertise.

Improve Your Mentoring Connection with Mentoring Software

Whether you’re a mentor, mentee or a program administrator, you know how challenging it can be to keep up with your mentoring relationship when you’re in an informal or manual mentoring program. A lack of structure or guidance can cause you to lose track of meeting times, notes from your last interaction or the tasks you agreed to with your partner.

Mentoring software makes it easy to keep track of your interactions, engage with your mentoring partner in the moment (whether on your computer or through a mentoring app) and stay focused on your mentoring goals and milestones.

Learn how Chronus mentoring software could help you and your organization level up your mentoring strategy for greater growth – both personally and professionally.

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