25 questions to ask your mentor or manager

One of the best ways to put your career on the fast track is to build relationships with and learn from others who have more experience than you. 

People who’ve participated in mentorship programs say the top three benefits are professional development, a better understanding of organizational culture, and the development of new perspectives. And even if you don’t have a formal mentor, you can learn a lot about professional development from your direct manager or other coworkers. 

But what exactly should you ask them and how do you get the most out of these conversations? Here are some tips and suggested topics to help you get started.

How to find a mentor 

Many companies and professional organizations have formal mentorship programs, so be sure to check if you have something like this available to you. If not, you can start by looking in your company and then expanding out into your existing network. Ask people you already know if they can recommend or introduce you to someone. You might also approach someone you meet through a meetup, conference, or other professional gathering.

When considering if someone would make a good mentor, NPR recommends defining your short- and long-term professional goals and defining who you look up to professionally. Yale also suggests finding a personality match—someone you’d get along with and who is happy with their career (though it may be hard to assess this before you have the chance to talk with them!). 

Both mentors and mentees tend to choose people from the same identity groups, but keep in mind that there are pros and cons to selecting a mentor whose background is very similar to your own. If you’re from a historically underrepresented or marginalized group, you may benefit professionally from having a mentor who shares elements of your identity. “Having a mentor who shares similar identities has been shown to lower instances of imposter syndrome,” write Philip Wilkerson, III and Samara Reynolds for the National Association of Colleges and Employers. But keep in mind that having a mentor with a different background and life experiences can also help widen your perspective and challenge you to think in new ways.

Once you’ve found someone you’d like to have as a mentor, make sure they have the time and interest to meet with you initially (and then on an ongoing basis). Ask them what you can do to make the relationship successful—do they want you to take the lead with scheduling calls or meetings? Would they like you to follow up in a particular way?    

Tips for asking questions

Conversations with your mentor are likely to be different from other conversations in your life. You may need to be more proactive in bringing up topics and directing the conversation to make sure your questions are getting answered. Here are a few tips to help you ask better questions.

• Try to ask open-ended questions. “What do you think about…?” is better than a yes/no question like “Did you like…?” Open-ended questions will encourage your mentor to provide more details in their answer and keep the conversation flowing.
• Ask follow-up questions. Sometimes people don’t know how much detail or specificity you’re looking for, so don’t be afraid to prompt the person to share more with phrases like, “Can you tell me a little more?” “Can you share more about…?” or “I’d love to hear more about that.”
• Be considerate when asking personal questions. It can be tricky to know what might be overly personal because this will vary depending on your mentor’s personality—some people talk openly about their families and life outside of work, but others prefer to stick to professional topics. Pay attention to how your mentor responds. If they look uncomfortable or hesitate to answer, you can say something like, “Only if you feel comfortable sharing.” Or you can offer some additional information about why you asked this question by saying something like, “It’s okay if you don’t want to answer, but I’m asking because…” 

Questions to ask when getting to know your mentor 

When getting to know your mentor, try to avoid asking them about things you can easily learn through a quick online search. Do some research before you meet them so you can ask more in-depth questions. Instead of asking where they went to college, for example, you can say something like, “I see you went to college at X. What appealed to you about that particular school or program?” Here are a few other questions to ask when getting to know your mentor.

• What have been the highlights/your proudest accomplishments in your career so far?
• What were some key moments that shaped your career path?
• What was your first job ever and how does it relate to what you’re doing now?
• What’s something that’s not listed on your resume that you feel defines you as a person?

Questions to ask when you’re seeking advice on a problem

When you’re seeking advice on a problem, be as specific as you can. Instead of asking, “How do I get better at public speaking?” say, “I’m going to give a five-minute presentation at a company all-hands. What are some ways I can avoid feeling self-conscious?” 

However, there is one caveat. If your mentor works in the same organization and you’re having an issue with a coworker, you may want to avoid sharing specific names and try to describe your problem more generally. 

In any case, try to sum up the situation as briefly as possible and let them know you’re happy to fill in more detail if necessary. Once you’ve described the problem, you can ask:

• Have you experienced something similar? How did it get resolved?
• What would you do in this situation? What would you recommend not doing?
• Which resources would you recommend?
• Is there anyone else you’d recommend talking to? If so, can you put us in touch?

Questions to ask when you’re considering a career change 

If you’re interested in making a career change, your mentor may be able to help you consider what types of roles and companies would be a good fit—or they may also be able to introduce you to people who can help. Here are a few questions you can use to guide this conversation.

• I’m interested in exploring [role/career change]. What would you recommend doing to pursue this?
• What opportunities do we have for internal transfers? Or how can I explore other careers while still in my current role?
• I’m interested in learning more about [role/team/industry/company]. Based on what you know about me, what do you think about this potential change?
• Would you be willing to make an introduction to [person in role/team/industry/company]? How can I help facilitate that?

Questions to ask about giving or receiving feedback

Feedback is an important part of professional development, but asking for and receiving feedback are skills that can take time to build. You can use your time with your mentor to learn how they approach feedback conversations. Once you know each other well, you might also ask them for feedback on your own skills or performance. 

General questions about feedback: 

• How do I get better at giving feedback to others?
• Which feedback frameworks do you recommend?
• What do you do when you receive feedback you don’t agree with?
• How should I respond when someone gives me feedback that’s hard to hear?

Asking for specific feedback:

• I’d like to hear your thoughts on [my performance/behavior/situation]. What feedback do you have for me?
• I’m trying to get a sense of my strengths and areas for improvement. What feedback do you have for me?
• How can I get better at [specific skill or behavior]? 

Questions to ask your mentor about career development 

Career development isn’t just about moving onto the next level of seniority in your company. It’s a complex, ongoing process that involves both self-reflection and action. You can use your time with your mentor to learn how they approached their own career development and get their advice on how to approach your own.  

• Which skills have been most important in your career so far?
• I’d like to learn more about [specific topic]. How should I go about doing that?
• Which skills do you recommend I focus on if I’d like to [accomplish specific task]?
• I’d like to [accomplish specific task]. What steps should I take to make this happen?

Other things to talk about with your mentor

Not every conversation with your mentor needs to be a Q&A session. Keep in mind that you can also use the time to role-play or discuss techniques for things like asking for a raise or promotion. Or you might want to practice an upcoming presentation and get their feedback on it. You may also occasionally want to ask your mentor for a favor like writing a letter of recommendation or facilitating an introduction to someone else. As with any other interaction with your mentor, remember to be clear about your goal and let your mentor know you’re happy to do whatever you can to make it as easy as possible for them.