questions to ask potential research mentor

Tips for Meeting with a Potential Mentor

In contacting a potential mentor, you should be prepared to convince the mentor that you are right for a position in their group and determine if the opportunity is right for you.

The way in which you approach a potential mentor will have a great deal of impact on whether you end up being recommended by the mentor to join their group. There are two key things you need to do in order to make a positive impression: (1) provide information about yourself, and (2) learn something about the research topic in advance of making first contact.

Providing information about yourself is relatively easy. Useful information includes class level, major, GPA, relevant courses taken, and any prior experience. If you have a resume available, this is very helpful. Learning something about the topic is a bit harder, but a little effort can go a long way. Take the time to browse through the mentor's website and look for any relevant publications authored by the mentor. Sometimes journal articles are posted directly on the website, or you can use the Web of Science library search to find articles on the topic written by the mentor.

Once you have collected the information about yourself and about the research topic, you are ready to contact the potential mentor. The best way to begin is by sending an email message introducing yourself and explaining why you are interested in the topic. This would also be an appropriate time to set up an appointment to meet or for a telephone or Zoom interview to discuss the research opportunity. You might also request additional references or websites you can read prior to your appointment.

The first meeting with a potential mentor is very important, whether you do it in person (the best way), or by e-mail, phone, or video conferencing. Plan to spend some time with this step. Don't wait until the last minute to begin this process.

This is your opportunity to find out what the project will be, why it is important, and how you might approach it. It is also your chance to find out what it will be like to work in the research group. If you have not previously done research, the interview should help you form your expectations about what the mentor wants from you and what you want from the experience. THIS IS VERY IMPORTANT! Your experience will be enhanced if you spend some time in this initial, vital step!!

And now, on to the first meeting.

We suggest you ask some--or all--of the following questions when you meet with a potential mentor. You will impress the mentor and help them think more deeply about your project. These questions are general guidelines; they are not a checklist. Ask all the questions you can think of! After you talk to your mentor, think about the discussion, and then go back and ask more questions.

Try to find out in detail what this project is. What is the science? What is expected? What led to this question? Ask for more articles or literature references about the project, especially articles by the mentor or members of the research group. Then read the articles and ask questions for clarification or further information.

What specific tasks are required to do this project? What course background or skills do you need to do it? What is the likelihood of completing this project in ten weeks? What equipment will you need to use? When will it be available to you? Will you work on this project? Or will you work on something different? Ask whether you are a strong candidate for this project. (If you are not, you may want to talk to other prospective mentors.)

Who will supervise you? Will you have a co-mentor, a grad student? Have they been informed you will work in the lab? How many other students have they supervised? How much supervision will they be willing to provide? Ask to meet the co-mentor (if it is not the faculty member or JPL staff member), and ask them the same questions. When your mentor/co-mentor is not available, who else can answer questions or help you?

What is it like to work in this laboratory? Are students welcome at group meetings? When are meetings? Seminars? Journal clubs? Could you start to attend group meetings now as your time permits? Will you get a chance to present your work to the group during the summer? Can you get a brief tour of the lab? When do people work?

Read, note, and inwardly digest the information you get as you ask these questions. Consider the mentor's responses--do they eagerly answer your questions? If they seem hurried or distracted, ask whether there would be a better time to discuss a possible project. When you have given thought to the project and your interview, go back and ask more questions about the project; dig more deeply into the science. After you think about your interview, consider whether you want to work with this person on this project for ten weeks. If the answer to that is "no," you may want to start the process with another potential mentor.

Interview guidelines were prepared by Carolyn Ash, Quondam Director, Student-Faculty Programs.

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Prospective postdocs.

• How To Apply
• Open Postdoctoral Positions
• Finding a Faculty Mentor
• Cost of Living
• Fellowships at Stanford
• Fellowships outside Stanford

How to Find, Approach, and Interview Potential Faculty Mentors

Postdoc appointments at Stanford are initiated by an offer from a faculty member. Selecting the best faculty mentor requires thought and investigation. Consider the following guidelines:

Start with your research interests and career aspirations.

What are your research interests? Your career aspirations? What excites you in your research field? Can you identify a productive research area that fits your values and career plans? Who is engaged in research that is complementary to your interests? Do you have geographical limitations?

What kind of mentor best fits your needs?

Famous mentors have connections and resources but may travel a lot and have big labs. Up-and-coming mentors may be in the lab every day but may still be developing resources. Do you prefer hands-on guidance or a more removed mentoring approach? Are they nurturing? Is that important to you? Are they collaborative? Competitive? What kind of connections do they have in academia? In industry? Where have former postdocs from that lab ended up? Read their work and work from their lab widely and critically.

Approaching potential mentors:

Introduce yourself via a succinct cover letter or email.

• The story of your current research (question, approach, results, and significance)
• Your career goals, your plan to achieve them, and how a postdoc position in that lab fits into that plan
• Your postdoc project interests (be creative!) and proposed approach
• A description of how this collaboration is a great match

Preparing for the interview:

Read up on the field in general, read the last several papers from the group, and research their current interests and projects. Think about the lab’s ongoing work. Conceive of complementary projects that aren’t in their current inventory. Prepare a 30-minute talk in advance; in this talk make it clear why you did what you did and the foundation of that work. Be prepared to answer some hard questions - don’t be defensive; discussing and defending your work is part of the process.

Questions to ask current/past group members (be selective, the focus should be on your science):

About them: Ask about their science and the lab environment.

About the PI:

• Is the PI a micro-manager?
• How often do you meet?
• Are they available for guidance?
• Do they play favorites?
• Are lab meetings confrontational or supportive?
• How responsive are they with manuscripts and deadlines?
• How is authorship/project ownership handled?
• About opportunities: Are there opportunities to teach/mentor? Leadership development?
• About the lab environment: What is the lab work ethic? What is the time off with pay policy in practice? Is there encouragement/financial support to attend major meetings? Who represents the groups at department functions? Is there formalized, regular feedback? How long do postdocs usually stay?

Questions to ask the faculty mentor:

What are the mentor’s expectations of a postdoc? How is a postdoc’s research program determined? How many postdocs has the mentor had? Where did they go? How many others are in the lab (grad students, staff, etc.)? How many papers are being published, and where? What is the mentor’s policy on travel to meetings? Are there opportunities for practice in grant writing, teaching and mentoring, oral presentations, and reviewing manuscripts? How long is financial support guaranteed? On what does renewal depend? Are there adequate research funds to support the proposed research? What is the mentor’s approach to help in finding a next position? How are projects shared?

Adapted from John Boothroyd’s “Finding the Right Postdoc for YOU,” Preparing for Faculty Careers, and “Questions to Ask When Choosing a Postdoc Advisor,” Pathways to Science.

Other Resources:

• How to Find a Mentor and Lab (Stanford Biosciences)
• Advising and Mentoring : the value of multiple mentors (Stanford Biosciences)
• Quintessential Careers : how to find a good mentor
• Council of Graduate Schools : mentoring topics for each stage of training
• How to get the mentoring you want  (University of Michigan)
• How to obtain the mentoring you need : links to other resources and guides (University of Washington)
• Stanford T32 Institutional Awards for Postdocs
• Postdoc Benefits
• Open Postdoc Positions
• Diversity in Postdoctoral Scholar Training
• Postdoc Emergency Resources
• Verify Appointments
• Funding Guidelines
• Budgeting for Fellowships

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• Preparing for the First Meeting

Your first meeting with a potential research mentor is an opportunity for you to learn more about a faculty members research interests, ongoing projects, any collaborators or graduate students or other faculty they work with, and what expertise and guidance they may give you in a potential research project. For the potential faculty mentor, the first meeting is a time for them to learn more about you, your motivations, your intellectual interests, and how they can be most helpful to you. Before you head into your first meeting with a potential faculty mentor, consider the following:

Prepare ahead of time Read up on the faculty member's most currently published papers or summaries of their work and reflect why the work is interesting, what you’d like to learn, and what ideas you also might have to contribute to the work. Sketch out a short agenda (for yourself) outlining the important points you’d like to make or questions you’d like to ask.

Potential Questions to Ask :

• Can you tell me more about your project on ...?
• How can I learn more about this topic? Are there papers or courses I should take to prepare myself?
• How do students typically get involved in research in your field?
• What would independent research look like in this field?
• Have you mentored undergraduates on independent research projects before? If so, how did they prepare for starting an independent research project under your guidance?
• What would a research assistantship for you entail? What are your expectations for a research assistant (time commitment, relevant skills)?
• What are your expectations of a thesis writer? (How often do thesis writers check in with you?)
• Are there any opportunities for me to get involved in research under your guidance or with your graduate student mentees or postdocs?

During the meeting Take notes and ask questions. Don’t be afraid of concepts that may come up on in conversation that are unfamiliar to you. Show your interest and curiosity for what they do, which will provide context for you to describe your interests in working with them. 

Post-meeting Review the notes you took during your first meeting. If you were seeking a faculty mentor for an independent research project, think about their research and expertise, their communication style and how they might be helpful. Keep in mind that a potential faculty mentor’s interests may not directly align to your own. if you feel that they have given you substantial information to consider and if you enjoyed the conversation and feel comfortable seeking their advice, they may a make good mentor for your research. If you are seeking additional expertise or other guidance, it is also okay to have additional mentors or advisors in the wings. Follow up with a thank you email, acknowledge that you have read papers that they have recommendeded, and ask what next steps there may be if you are interested working more closely going forward.

• Getting Started
• Identifying and Contacting Faculty Mentors
• Setting Expectations for Working Together
• Maintaining Mentee/Mentor Relationships

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Office of Undergraduate Research

Research mentors: who, why, and how, by shreya murthy, our peer research ambassador.

There’s no question that if you are interested in research for any reason, it is a valuable experience. However, one the most important parts of the research process is finding a research mentor. The information below will help you navigate this step.

Who Are They?

Research mentors are usually faculty members or graduate students who support you through your research journey. Mentors are there to guide you through the many ups and downs of the research process. They can and sometimes will change as you develop as a researcher and your needs and interests change. You may have more than one mentor as you move through your research endeavors.

Why Are They Important?

Mentors are your first point of contact for general research questions or concerns. They are there to be sounding boards for struggles, provide key suggestions of resources or other people to consult, and review materials as you move toward presentations of your work. They are also there to help you manage your expectations. One of the most helpful pieces of advice that my mentors continue to give me as I work on my research is that I need to be realistic about my project goals and to be careful not to bite off too much. Mentors are also great people to talk to about potential careers in your field or help with graduate school applications and planning for your future. They can suggest programs, write you recommendations, or help you find other opportunities.

How Do You Find One?

Finding a mentor is always the hardest part, as it requires a lot of effort to build that relationship. There are many ways to begin making these relationships, including going to a professor’s office hours to discuss their research and your interests or through an honors conversion project. You can also begin with an email to get help synthesizing an idea that you have. It is important to note that while having a mentor related to the field you are studying, finding one that perfectly matches with everything that you want to do is also not necessary. You want to look for a mentor who you work well with, and who can guide you through your research and future endeavors.

How Do You Maintain the Relationship?

Once you find a mentor, make sure you regularly communicate with them or meet with them. Don’t wait for something to go wrong with your project before you reach out. Send them an email or schedule a meeting. Don’t be afraid to ask questions or even ask how the mentor would prefer to communicate about your project. Be proactive!

Mentors are really amazing people who have a lot of experience that they are more than happy to share. They are great resources for your research and professional career.

Shreya is a junior majoring in Criminology, Human Rights, and Finance, with a minor in Political Science. Click here to learn more about Shreya.

70 questions to ask a mentor for a great mentorship experience

Did you know? We have over 3,000 mentors available right now!

Knowing how to ask good questions to a mentor is key to a successful mentoring relationship. At MentorCruise, our mentees often wonder how to ask the right questions that will lead to meaningful exchanges between the mentee and mentor.

Did you know? We have over 2,000 mentors available right now!

After all, there are so many questions but not enough time to ask them all during mentoring sessions. Whether they’re  on mentoring topics  related to  career paths , job search,  how to ace job interviews , leadership lessons and so on, asking the right questions to your mentor is more of a skill you can improve upon with the right tips.

As a  mentorship platform , we’ve hosted so many successful mentorships. Many of them partly attribute their success to asking the right questions. As such, we’ve decided to put all their key learnings on how to ask the right questions into a guide.

You’ll learn:

• Tips on how to ask good questions to your mentor
• Topics to discuss with your mentor
• Questions your mentor could ask you
• 70 good questions to ask a mentor

7 Tips on How to Ask the Right Questions to a Mentor

Before we dive into what questions to ask a mentor, read these seven tips to get the most out of your mentor-mentee relationship:

1. Ask clear, specific questions instead of vague ones

In your mentoring questions, good questions to ask your mentor are those that are clear and relevant to the mentor’s expertise. Normally, when people look for a mentor, they’re looking for guidance to solve a specific issue in their career.

Figure this out: You’ve decided to get a mentor so that you can learn how to become a better leader. You get into the topic of public speaking because it’s been a lingering issue of yours.

Here are two examples that roughly ask the same question, but one is more specific and the other a bit vaguer:

A: “How do I become better at public speaking?”

B: “What do you do to avoid nervousness when speaking in public?”

A is an example of a bad question to ask if you want meaningful advice precisely because it’s too vague. Why is it not appropriate for a short mentoring session? Because it’s a public speaking question that requires a resounding answer to be effective.

On the other end, B asks a more specific question about nervousness when speaking in public. The mentor can give more actionable advice on this because it’s more specific. You’ve defined the problem concerning public speaking that you need mentoring with.

2. Ask questions on these key topics to get the ball rolling

Coming up with questions to ask a career mentor can be tricky. To help you out, you can try asking common mentorship questions that lead to meaningful conversation and action. For example, you can ask questions on these mentoring session topics to get to know the mentor better and initiate a good conversation:

• Expertise, career development, self-improvement, and building skills. You can ask for specific advice on how to learn and develop a skill or for actionable tactics to help surmount a particular obstacle.
• Stories. Storytelling is a craft that humans naturally gravitate to as social creatures. Relationships develop through sharing stories that help us connect with one another. This principle also applies to your mentoring relationship.
• For example, if you have a  startup mentor, you can ask this story on risk-taking : “What was that one time you took a huge risk and it paid off?” This question can give important insights and will help the mentor become more open with their feelings by telling you their personal stories.
• Situational. Ask about more specific issues regarding your career or theirs. Here’s a sample question on leadership lessons: “My boss told me to take ownership of my managerial tasks. What does that mean?”
• Here’s a question that most experienced managers will know how to answer but may still initially confuse newer ones. If your mentor is much more senior than you and has been in a position of influence, they will know how to answer this.
• Accountability. From time to time, it’s important to circle back and ensure you’re correctly following your mentor’s advice. Ask questions on improving your rapport or if you’ve been making good progress throughout this mentorship.
• Career development and growth . Knowing the next steps in your career can help you plan ahead. Talk about your personal growth and industry factors to get a robust sense of upcoming milestones.
• Career path. No career path is linear. By asking a mentor about career path questions, you can find out if you’re in the right career and how you can incorporate other interests/passions into your work.
• Leadership . Leaders are made, not born. Ask your mentor about what’s important to be a good leader and how to resolve conflicts within your teams.  Entrepreneurship  and business. Finally, starting your own business or cultivating an innovative mindset can be vital to your work. ​ Talk about good entrepreneurial habits and advice about becoming a business owner.

Of course, questions for your mentor don’t have to fit into these categories. These are simply starter topics, but you can write up your own questions to ask a  career mentor , too.

3. Avoid asking rhetorical questions and keep small talk to a minimum

Don’t force a conversation. Your first session will always be the most awkward one. You and your mentor have just met each other for the first time, so you will still need to figure out how to go about this interaction.

Instead, ask the types of questions highlighted in the second tip and be very specific in the way that you’re asking them. More often than not, these tips improve the quality of your conversations and allow you to develop deeper mentoring bonds.

In the worst-case scenario, MentorCruise allows you a 7-day free trial for first-time mentorship sessions. You can end the relationship when you’re not feeling a connection between the mentor and yourself.

4. Be prepared

The worst thing that you do in your mentoring sessions is to come in unprepared, with no specific questions to ask your mentor. This mentorship experience has been built based on your desire for self-improvement. If you don’t want to achieve your goals, then there’s no point in continuing this mentorship.

Mentorship is an investment in time and energy. Being unprepared implies you’re not interested enough to make this mentorship work. And in return, your mentor might grow to care less about your progress. After all, a great mentoring relationship is partly predicated on a mentor who wants to see you succeed, so you have to put in the hard work.

5. Use a mentoring agenda template

A mentoring agenda template is an excellent way to support you in asking the right questions, and this type of preparation shows your mentor how keen you are to succeed. During mentoring sessions, it’s easy for several questions to come to mind, and an agenda can be used as a reference to help ask questions that stay on task and leverage your time together.

You could send your agenda to your mentor before the first meeting so you arrive on the same page. Furthermore, your mentor may want to bring a schedule. If so, there’s no harm in merging the two!

A mentoring agenda template is customizable. We’ll use the mentorship action plan below as an example of how you can prepare an agenda for your mentor meetings:

6. Goal setting

When setting goals and development priorities for your action plan and mentoring agenda template, you’ll likely follow the  most effective goal-setting method : SMART (specific, measurable, achievable, relevant, and time-bound). SMART goals help focus your efforts and make your mentor’s job of tracking and assessing your progress easier.

Here are some high-level “Individual” and “Corporate” goal examples that would be expanded on using a goal-setting technique:

• Individual goal (long term):  A personal goal  could be to lose 100 pounds in 12 months.
• Individual goal (short-term): To achieve the long-term goal, a micro-goal could be to lose 8-9 pounds each month.
• Corporate goal (long term): Improve customer service by the end of the year. Here,  the SMART goal method  would be good for clarifying what a customer service improvement is. Thus, knowing whether the goal has been achieved or not.
• Corporate goal (short term): One way to improve customer service could be faster ticket resolution by resolving problems at the first point of contact, where possible. A short-term goal could be to ensure a 10% reduction in incident tickets going to third-line teams.

Consider the actions/activities you can incorporate into your daily routine to achieve your goals, and perhaps these ideas can be added to a “notes” section.

7. Know the mentoring session topics your mentor might discuss

For productive and flowing sessions, be prepared for some of the topics your mentor may use to initiate conversations.

Mentors know the skills they can offer you. However, they’ll need to judge how best they can use their skills to help you. They’ll discover your objectives and challenges by asking you extraordinary questions.

When you’re familiar with the types of questions your mentor may ask you, you can lightly prepare your answers and think of follow-up questions to ask them. For example, they could ask you how you overcame a challenge at work. As a follow-up question, you could ask for tips on how you can improve your method or how else you could tackle the problem.

Here are some examples of topics your mentor may discuss:

Career journey

• Did you plan your career, or did it happen naturally?
• How would you describe your dream job, and do you feel you’ve achieved it?
• If you could turn back the clock, would you choose a different career?
• How can you adopt a mindset of continuous learning?

Long-and short-term goals

• What quantitative goals do you wish to achieve within the next 1 – 6 months?
• What interested you in working with a mentor?
• What other positions are you interested in within the company?

Company related

• How do you think your role and contribution benefit the company?
• How do you consider the business could be improved through your role?
• How would you describe your company’s culture, and do you feel it resonates with you?
• What methods do you use for effective communication?
• What leadership skills do you already have?
• What leadership skills do you need to develop?
• How would you describe your leadership style?
• How do you feel about your responsibilities? Do you have any uncertainties?

Strengths and weaknesses

• Do you think your current role allows you to leverage your strengths?
• What areas of your job do you consider your weaknesses impede you?
• How do you mitigate your weaknesses?

Getting to know you

• What inspires you?
• If you could learn another professional skill unrelated to your current role, what would it be?
• What’s your favorite superhero, and why?

8. Asking questions is just the start

Having great questions to ask a mentor is just the start of a successful relationship. Your questions should lead to meaningful exchanges and guide your next steps.

In this way, use questions as a sounding board for action. From your ongoing list of  questions and mentorship topics , identify ways to build your career together.

For example, after asking your mentor questions about entrepreneurship, you might come up with a plan to build your business mindset, including leaders to follow and books to read.

Or, as part of your mentorship relationship, you might troubleshoot a current team dilemma and talk about leadership traits to cultivate this next quarter.

Finally, questions you ask a mentor about career development may lead to  actionable mentoring goals  such as improving your networking or interviewing skills.

70 Strategic Questions to Ask a Mentor

Here are boilerplate questions to consider asking a mentor during your sessions. Don’t forget to create your own twist for each question.

Remember that mentorships thrive when mentees ask specific questions instead of vague ones. These are meant to be open-ended questions that you can turn into something more specific.

And one more thing: context is key. Contextualize your questions before or after asking. This helps the mentor figure out how to give meaningful answers.

Take a look at these mentorship topics to get a better idea of what you’re interested in. You can maximize your mentorship experience by asking questions about career development, growth, leadership, career path, entrepreneurship, and more!

Without further ado, here are 70 strategic questions to ask your mentor.

Expertise, self-improvement, and building skills

• Where do you think my strengths lie in?
• How can I develop the right discipline to achieve my goals in this industry?
• What are the  necessary skills  that I should develop to rapidly grow in my career?
• What are some things in your career that you regret not having done earlier?
• How do I effectively manage my time and prioritize accordingly?
• Do you even get impostor syndrome? How did you learn to get over it?
• Did you have a hard time starting out in this industry?
• What are some hard choices that you made to get where you are in your career?
• Did you experience some major setbacks in your  business/career path ? How did you bounce back?
• What are some instances that you would have done differently?

Situational

• How do I handle this situation better?
• Do you have some  tips for networking  online? This question is even more relevant today as more companies embrace working from home.
• I feel stuck. What are some ways that I can apply to solve this issue?
• My boss and colleagues are treating me unfairly. Based on your professional experience, do you think I should move elsewhere?
• I have a job interview coming up. What are some  interview questions  and other things that I need to know about to nail it?
• Do you have any tips on improving my resumé for my job search?
• How do I prepare myself for performance reviews?

Accountability

• What would you like to see me do every week to show that I’m improving throughout this mentoring program?
• Am I progressing in the right direction through this mentoring program?
• Am I correctly listening to your skills or career advice during each mentoring session?
• Are there any other topics you’d like for us to discuss?
• Do you have any feedback on how we can improve our mentoring rapport?
• Do you have any negative feedback or criticisms I can use to improve myself?

Career growth and development

• How can I refine key skills for my career?
• How can I stay competitive in my line of work or at this career stage?
• How can I apply my strengths in my daily work?
• Who should I connect with to improve my career prospects?
• How is my industry likely to change in the next 5 years? In the next 10?

Situational questions to ask a work mentor

• My boss always shuts me down in meetings. What’s the best way to respond when it happens?
• I’ve recently been promoted to a position I know my coworker wanted. I know they resent having to report to me now. What’s the best way to handle this situation?
• I feel my toxic work environment is beginning to affect my health. However, I’m scared to leave my job. What do you think I should do?
• I’ve taken over from a fantastic leader whom the team was very fond of and missed. Unfortunately, I feel like they resent me and want their old boss back. How can I cut through the team’s hostility and get them to at least respect me as their new boss?
• I feel as though my current role suffocates my creativity. How do you think I can make the situation better?
• I’m constantly having to complete or re-do my coworker’s work. What should I do?
• I’d like to apply for an opening in another department, but that department and my current department aren’t on the best working terms. I’m concerned about how the new department will receive me. Do you think I should still switch to that department?

Career path

Questions to ask a mentor about career paths may vary according to your needs. For example, if you want to  change careers , you might have specific questions about the industry you’re interested in.

Here are some initial questions about building your career path to get you started:

• What are the first steps to changing a career?
• How can I combine my interests or passions at work?
• How can I become more proactive about my career direction?
• How can I incorporate meaning into my career?
• What good habits should help me focus on my career?

Questions to ask a cyber security mentor

• How did you get into cyber security? What sparked your interest?
• What were some hurdles you experienced in becoming competent and skilled in cyber security?
• What are the most helpful certifications or company resources to become a [cyber security role]?
• What has helped you to overcome the challenges in this industry?
• What do you enjoy the most about working in cyber security?
• How do you see the industry’s future changing over the next ten years?
• What is something you think most clients don’t understand about cyber security?

Questions to ask a project manager mentor

• What knowledge, skills, and abilities are required for project management competency?
• How do you get started with a new project and set it up for success?
• What is more important to a project’s success, the project manager’s soft or hard skills?
• How do I stand out from my peers? What qualities do you think I need to develop?
• How can I be a more strategic project manager?
• What strategies have you found successful in project management?
• What techniques do you recommend for managing stress?
• What leaders do you look up to for inspiration?
• What are some books you can recommend on leadership?
• How do you keep your team motivated?
• What qualities are lacking among today’s leaders?
• How do you continue to grow and develop as a leader?

You can think of questions to ask a career mentor related to their personal experiences as well. For example, you might want to ask about:

• What was your worst leadership decision?
• What was the worst conflict you had to resolve?
• What was the biggest leadership risk you took?
• What was your proudest moment as a leader?
• What are your current goals as a leader?

Entrepreneurship and business

• What do you enjoy most about entrepreneurship? What is hardest about it?
• What are some mistakes you wish you could have avoided?
• What advice would you give to newbie entrepreneurs?
• How do you brainstorm and finalize business ideas?
• What are the biggest mistakes first-time entrepreneurs can make?
• How do you plan on growing your business or entrepreneurial mindset?
• What was the toughest moment in your business journey? How did you overcome it?
• Is there any popular entrepreneurial advice that you agree/disagree with? Why?

If you’re considering starting your own business, you can also ask for specifics about the business name, entity, business plan, funding, publicity/marketing, scaling, and competition. And if that wasn’t enough, you can get  even more entrepreneurial questions to ask a mentor  here.

Insert your mentorship question here

Finally, you may still have questions to ask a mentor that doesn’t neatly fall into these categories. No problem! Come up with your own questions to ask a career mentor so that you can make the most of your mentorship relationship.

After all, the mentorship experience is all about your needs, so write up those questions that don’t fit into the topics above about career development, growth, leadership, career direction, entrepreneurship, etc.

Join MentorCruise to find the right mentor for your professional needs

In this guide, you’ve learned how to ask the right types of questions in your mentoring sessions and questions to consider asking, helping you to achieve success in your mentoring efforts.

Remember that asking your prospective mentor the right questions is only one part of the equation. You also already need to learn how  to choose the right mentor  to help you achieve your goals and get the career advice that’s right for you.

The road to career success  is often a bumpy one, and career development may often seem confusing. But imagine how much easier it would be if you had an experienced industry leader available anytime to offer career advice and expert guidance. At  MentorCruise , you can pick through many experts and industry leaders to see the right mentor for your needs.

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73 Mentorship Questions to Ask Your Mentor or Mentee

• January 25, 2023

It’s common to struggle to find questions to ask your mentor or mentee. Getting to know your mentoring partner can feel awkward or even vulnerable – but this is normal. Building rapport with your mentoring partner and creating a space of psychological safety is key.

So before we go into what questions to ask your mentor or mentee, let’s hear from Janet Phan as she describes how she has navigated that journey herself:

So if you’re feeling stuck, we’ve crafted this list of engaging questions sure to spark conversation with your mentor or mentee, help you go deeper, and add some extra structure to your meetings to ensure you get the most out of them.

But first, if you’re a mentee, we want to make sure you’ve had a chance to look at and work through this first meeting checklist . It will help you better understand your mentor – their background, experience, and what they’re bringing to the table. It will also help you better articulate your goals for the mentorship and help you both give and receive feedback.

If you have completed this checklist, why not check out these four mentoring session guides ? They can further help you construct your sessions to pack more of a punch. Whether you choose the Storyteller, Guru, Situation, or Skill-Builder session guide, you’ll get to know your mentoring partner in a new light with each one.

Once you’ve worked through those, you’ll still need some questions for further down the relationship. So without further ado, here is a list of mentorship questions to ask your mentoring partner.

73 Mentorship Questions

We’ll first look at good questions to ask a mentor, then questions for a mentor to ask mentees.

Questions to Ask Your Mentor

When meeting with your mentor, it’s important to come prepared with questions. This will show them that you are serious about the mentorship process and are committed to making the most out of it. Questions to ask your mentor include:

• What can I do to maximize my progress during this mentorship?
• What do you think I should prioritize when it comes to my goals?
• What methods do you use when dealing with difficult situations?
• What is the best way to communicate with you?

Need to break the ice first?

Here are some fun, quirky questions to break the ice and get to know a different side of your mentor, one that might not be immediately apparent in his or her professional persona.

• If you could be an animal, what would you be and why?
• What would the title of your autobiography be?
• What was your favourite toy as a child?
• What’s an activity you did a lot when you were a child that you wish you could do more of now?
• Do you remember one of the first things (a pet, toy, etc.) you named? Why did you name it that?
• If you could curate a museum gallery, what would you put in it?
• What TV or movie character is most like you, and why?
• If you could combine any two animals, what would they be? What would you call this new animal?

Once you’ve had some fun with these questions (some responses can be quite telling!), it’s time to get a little more insight.

Dive into your mentor’s professional past

• What was your first-ever job? What did you love and hate about it?
• Did you think you’d find yourself in this industry? If so, when did you know this was the work you’d go into? If not, how did you get here?
• What would be your dream job?
• How do you make yourself happy in your current role/industry?
• What’s something you’d like to change about your current role/industry?
• Did you have a mentor at some point in your career? If so, how did s/he help you? If not, why did you never seek one out?

Questions for Mentors to Ask Mentees

Now it’s time to flip the script! Mentors, here are some questions you can ask your mentee on both the personal and professional front to better understand them and why they’re interested in this mentoring partnership.

Asking your mentee questions will help you to understand their needs and motivations, and develop more effective ways to support them.

Common questions to ask your mentee include:

• What drew you to this opportunity?
• What do you hope to achieve through our mentorship?
• What do you consider your strengths and weaknesses?
• How do you like to receive feedback?

Next, we’ll dig into the professional side of things a bit more.

Exploring your mentee’s experience

• Who do you talk with about the struggles and successes of your job?
• In your current role, have you ever thought about quitting? Why?
• Do you feel you are a part of a community, either in or outside of work? Who makes up that community and how do you support one another?
• If you could learn any new professional skill (it doesn’t have to be related to your current role or industry), what would it be?
• Where do you ultimately want to end up in your career (role, title, income, etc.)?

Need to get to know your mentee more?

• What was your favourite gift you received from the Tooth Fairy?
• If you could learn to play any instrument, what would it be?
• Who’s your favourite person (friend, family member, etc.)?
• What’s something silly that made you angry as a kid?
• What superhero do you resonate with the most? Why?
• If you could have the life of any famous artist or musician (dead or living), whose would you choose?

Explore Our Mentoring Session Guides

Still stuck? Go ahead and explore our four types of mentoring sessions . Approaching your mentoring catch-ups in a variety of ways assists in building rapport, exploring new areas and reflecting on your own experiences while learning about others’ experiences too. 

Let’s also dive into a few more ways to strengthen a quality mentoring relationship along with some tips and questions to ask yourself.

How to Foster a Positive Mentoring Relationship

Once you have established your mentorship relationship, it’s important to maintain it. This means establishing an open line of communication, setting clear goals and expectations, and encouraging open dialogue. It’s also important to establish trust, constructively provide feedback , and be consistent in your approach.

Questions to ask yourself include:

• What methods can I use to ensure effective communication?
• How can I make sure that our relationship is built on trust?
• How can I ensure that my advice is constructive and helpful?

Benefits of Establishing a Mentorship Relationship

Establishing a mentorship relationship can be beneficial for both parties involved. Mentors gain the satisfaction of providing guidance and helping someone reach their goals, while mentees get the benefit of gaining valuable knowledge and insight from someone who has experience in their field.

• What motivates me as a mentor?
• What do I hope to gain from this relationship?
• What are some potential obstacles I may have to overcome?

Tips for Effective Mentoring

Mentoring isn’t always easy – it requires patience, understanding and guidance. Here are some quick mtips for effective mentoring: Listen attentively, provide honest feedback and constructive criticism, be patient and understanding, set clear goals and expectations, provide resources and advice, encourage open dialogue, and celebrate successes.

• How can I ensure that I am providing effective guidance?
• What methods can I use to ensure that our conversations are productive?
• How can I make sure that my advice is helpful?

Best Practices for Connecting With Your Mentor or Mentee

Establishing a connection with your mentor or mentee is key to having a successful mentorship relationship. Best practices for connecting with your partner include: regularly setting up meetings for discussion, being open and honest about your expectations and goals, creating an environment of mutual respect, listening attentively and providing honest feedback, being consistent with your approach, and showing appreciation for your partner’s efforts.

• How can I ensure that our relationship is based on mutual respect?
• How can I make sure that our conversations are productive?
• What methods can I use to show appreciation for my partner’s efforts?

How to Make the Most of Your Mentorship Experience

Making the most of your mentorship experience requires effort from both parties. Here are some tips for making the most of it: Set realistic goals, be open and honest about expectations and challenges, be consistent in your approach, provide constructive feedback, listen attentively and give honest advice, maintain an open line of communication, and encourage open dialogue.

• How can I ensure that our relationship is based on trust?

Challenges of Being a Mentor or a Mentee

Being a mentor or a mentee comes with its own set of challenges . As a mentor, you may find yourself having difficulty providing guidance or advice in certain situations. As a mentee, you may find it challenging to stay motivated or keep up with the expectations of your mentor.

• What are some potential obstacles I may have to overcome as a mentor or a mentee?
• How can I ensure that our conversations stay productive?

Building Trust in the Mentoring Relationship

Building trust between both parties is essential for a successful mentorship relationship. This requires open communication, setting clear expectations and goals, consistency in your approach, providing feedback in a constructive way, listening attentively and providing honest advice.

• How can I ensure that my advice is helpful?
• How can I make sure that our conversations stay productive?
• What methods can I use to build trust between myself and my partner?

Setting Goals and Expectations in the Mentorship

Setting clear goals and expectations from the beginning is essential for a successful mentorship relationship. This involves discussing what each party hopes to gain from the experience, setting objectives that both parties agree on, and establishing deadlines for achieving these objectives.

• What kind of goals should we set for this mentorship experience?
• How often should we review our progress?
• How can we ensure that we are both working towards the same objectives?

Encouraging Open Communication in the Mentorship

Encouraging open communication is important in any relationship. In a mentorship relationship, this means establishing an open line of communication between mentor and mentee, being honest about expectations and challenges, listening attentively and providing honest feedback, being consistent with your approach, and thanking each other for their efforts.

Dealing With Difficult Situations in the Mentorship

Dealing with difficult situations in a mentorship relationship requires patience, understanding and guidance. It’s important for both parties to remain calm and be open about their concerns or disagreements. It’s also important for both parties to remain respectful of each other’s views and provide constructive feedback.

• How can I make sure that our conversations remain productive?
• What methods can I use to foster an environment of mutual respect?

Strategies for Maintaining an Effective and Productive Mentorship

Maintaining an effective and productive mentorship requires effort from both parties. Strategies for doing so include: Establishing an open line of communication, setting clear goals and expectations, listening attentively and providing honest feedback, being consistent with your approach, providing constructive criticism when necessary, celebrating successes, and showing appreciation for each other’s efforts.

How to Evaluate the Success of Your Mentorship

Evaluating the success of your mentorship is essential in order to ensure that both parties are getting the most out of it. Evaluation should involve tracking progress towards goals, reflecting on successes and areas of improvement, finding ways to overcome any challenges, providing honest feedback and support, and celebrating accomplishments together.

• How often should we review our progress towards our goals?
• What methods can I use to provide constructive feedback and support?
• How can I ensure that our conversations remain productive?

Ways to Celebrate Milestones in the Mentorship

Celebrating milestones in a mentorship relationship is an important way of showing appreciation for each other’s efforts. This could involve treating each other out for lunch or dinner, taking time out together for an activity such as bowling or miniature golfing, or sending each other cards or gifts as tokens of gratitude.

• How often should we celebrate milestones together?
• What activities could we do together as a way of celebrating our successes?
• How can I show my appreciation for my partner’s efforts?

What Not To Do When Establishing a Mentorship Relationship

When establishing a mentorship relationship it’s important not only to know what you should do but also what not do.

Things not to so likely include:

• Making assumptions about your partner’s abilities or expectations without discussing them first
• Imposing your own expectations on your partner
• Avoiding difficult discussions
• Taking criticism personally
• Not setting clear boundaries
• Not making an effort towards maintaining open communication
• Not listening attentively
• Not showing appreciation for your partner’s efforts
• Failing to celebrate successes together
• Being inconsistent with your approach
• Not providing constructive criticism when necessary
• Setting unrealistic goals
• Not making an effort towards fostering an environment of mutual respect

Ideas for Activities That Can Enhance the Quality of Your Conversations

Enhancing the quality of conversations between mentor and mentee requires effort from both parties.

Ideas for activities that could help include:

• Reading books or articles related to your field together
• Role-playing different scenarios related to the topics discussed
• Participating in webinars or workshops related to your field
• Creating an agenda prior to each meeting covering specific topics or questions
• Brainstorming potential solutions together
• Taking time out each week specifically dedicated towards talking about challenges or successes

For more insight into how you can make your mentoring relationships fruitful, check out the stories from the mentors and mentees in Mentorloop-powered mentoring programs:

Wrapping Up

It’s not uncommon for both mentors and mentees to be unsure if they’re a good match or not. That’s because it’s normal to get stuck getting to know a mentoring partner. 

We understand that building rapport is the best way to get the most out of your mentorship experience. Hopefully, these quirky and digging mentorship questions will help you get to know your mentor or mentee on a more personal level and provide more common ground.

Got a few more questions up your sleeve that we should add? Let us know!

If you’re ready to create a culture of intentional mentoring at your organisation, Mentorloop can help. We’ll get you started by building a custom mentoring program for your business, with guidance on how to get the most out of it, step-by-step.

Now’s the time to harness the power of mentoring and put it to work for your organisation. Build your Mentorloop-powered mentoring program today!

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Finding a Mentor

Identifying a research mentor is an important first step to engage in research, some questions to ask yourself.

• What am I looking for in a mentor?
• Why do I want to research? Curious about a biomedical problem, need to build my skills and experiences for residency, other?
• What type of research team am I looking to join? Studies basic science/mechanisms of disease, clinical, translational, other
• How much time do I have for research?
• Am I interested in the MSSRP, Research year, or M3/M4 research blocks?
• Am I ready to contact faculty? I have read about their research, my CV is up to date and focused, cover email prepared

How to use BU Profiles to identify potential mentors

Many research projects at BUMC occur in specialized centers, basic science departments, and clinical departments. Do not limit your  search to specific departments as you will often miss many interesting opportunities.

• BU Profiles Search

BU profiles includes a search engine that can be used to identify potential mentors.

If you would like to start a self-guided mentor search, one strategy is below:

• BU Profiles search guide

We would also be happy to meet, discuss your research interests & goals, and help you identify potential mentors.

Tips for contacting potential mentors

• Tips for contacting faculty about research

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Build relationships with mentors

Suggestions for integrating into your group and working to develop a strong relationship with your PI and daily supervisor.

Developing strong positive relationships with your PI, other research supervisors, and members of the research group will help you thrive at NIH. At the outset, it is important to clarify three functions provided by your PI and other senior leaders in your research group:

Supervision - Making sure work gets done, setting assignments, and focusing on the needs of the group.

Mentorship - Supporting the scientific, personal, and professional needs of individuals. Mentorship functions are sometimes in conflict with the overall needs of the team or supervisor; appreciating the potential for tension in these two domains is critical.

Advocacy - Speaking up on behalf of an individual in the group to support their career advancement. Advocacy generally happens later in a relationship especially as it develops in healthy ways.

Your PI and other supervisors provide all three of these functions, especially when it comes to your development as a scientist. However, one person cannot meet all of your needs and it important to cultivate relationships with other mentors and advocates. To help you build positive relationships with your PI and others who can support you, we offer guidance in four areas:

Understand and establish expectations

Guidance on what you should expect, and what is expected of you.

Integrate into your research group

Tips for success and common issues during the transition to a new work environment.

Develop a network of mentors

Advice on how to expand your mentor support system.

Where to turn when issues arise

Resources and guidance for navigating workplace conflict.

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37 Key Questions to Ask a Mentor to Transform Your Career

Have you found the perfect mentor, but are unsure of what steps to take next? What questions can you ask them to get the most out of the time you have together? What areas should you focus on to accelerate your growth?

Recently, we wrote a post on everything you need to know about where to find mentors , what qualities to look for in them, and how to approach them. It’s one of the most comprehensive mentorship starter kits you’ll find.

Today, we expand on our guide and share 37 questions you can ask your mentor to fully develop your relationship with them, and maximize your growth as a leader.

37 Questions to Ask a Mentor to Supercharge Your Career Development

If you need a reminder of what a mentor can do to boost your career, look no further.

Research has shown that people with a mentor exhibit greater confidence, earn promotions more quickly, and find jobs easier than their non-mentored colleagues. Wouldn’t we all like that? 

That’s why in our previous post on mentors , we covered topics including: 

• How you can find a mentor
• Three qualities to look for in a mentor
• How to approach them
• How to make the most of the relationship you have with them

With that in mind, it’s vital to know what to ask your mentor to make sure you’re putting the relatively limited time you have together to good use. We’ve compiled 37 questions you can ask about various topics to help you prepare.

1. Questions about improving your soft skills

"Success in dealing with people depends on a sympathetic grasp of the other person’s viewpoint." – Dale Carnegie

One of the biggest challenges of growing as a manager is finding ways to improve your soft skills. Unlike with an IC role, being a manager is much more of a people job and requires more soft skills as you progress through your career. 

In fact, research conducted by Harvard University, the Carnegie Foundation, and Stanford Research Center uncovered that 85% of job success comes from having well‐developed soft and people skills. In contrast, only 15% of job success comes from knowledge and technical skills.

Unfortunately, soft skills aren’t something you can learn from online courses or books alone. A big part of learning them is through experience. For many managers, mastering these skills is thus a very steep learning curve.

This is where the help of a mentor can be priceless. They can give you advice on exactly how to approach particular situations and share examples of how they’ve improve their vital soft skills.

There are many soft skills you need to learn to become a great manager, so make sure you get their input on the following topics:

• What are your favorite tips for having great 1:1 meetings?
• How can I get buy-in for my ideas? 
• When have you had buy-in go wrong and what did you learn from it?
• How do I become a better listener?
• What are the best ways to build rapport with my team?
• What can I do to become a more empathetic leader?
• What other soft skills do I need to master to be a great manager?

Your mentor will likely know all about the different subtleties of soft skills and connecting with your team on a more human level. They can share what’s worked for them, as well as key, hard-earned lessons from their own mistakes. Both can help you grow.

If you take advantage of that and ask them the right questions, you’ll be improving in areas that have been proven to separate great managers from average ones.

And to complement learning from their stories and example, here are resources you can check out to work on these areas on your own:

• The Ultimate One on One Meetings Template (+ Free Checklist)
• How to Get Buy in at Work: Making your projects more successful
• How Managers can be more Effective Listeners to Better Lead their Teams
• 82 Ways How to Build Rapport with Anyone at Work
• 3 Ways to Better Manage Up By Developing Empathy

2. Questions about working on your growth mindset

“Learning never exhausts the mind.” ― Leonardo da Vinci

Adopting a growth mindset should be one of your highest priorities if your aim is to keep getting promoted in your career. 

According to Stanford psychologist Carol Dweck and her TED talk , if you believe that people (including yourself) can't change or improve, you’ll never be able to take the initiative for your own or your team’s growth.

Conversely, if you believe in continuous improvement, are willing to face challenges head-on, and persist in the face of setbacks and criticism, you’ll open up a sea of opportunities for yourself.

Here’s a great visual of how a growth mindset works compared to a fixed one:

As you can see, people with a growth mindset are always looking for new sources of inspiration to learn from.

And having a mentor is a great way to feed a hungry mind and find untapped opportunities to grow yourself and your team. You can ask your mentor the following questions to make the most of your growth mindset:

• What are the best leadership books you recommend?
• What are the best management courses/resources you think I would benefit from?
• How do I help my team improve their skills and grow when I’m not an expert?
• How do I grow my team when I can’t promote them?
• How can I become a better coach to my team?
• How do I recognize and develop potential future leaders on my team?

With answers to these questions, you’ll keep evolving as a leader and find new ways to help your team grow, too. 

And to get more ideas to complement what they tell you, check out these links below:

• The 10 Best Books For New Managers On Leadership And Self-Improvement
• How to grow your team when you can’t promote them
• Books for Managers: 3 Books Every Leader Should Read

3. Questions about productivity

“Time management is an oxymoron. Time is beyond our control, and the clock keeps ticking regardless of how we lead our lives. Priority management is the answer to maximizing the time we have. ” - John C Maxwell, best-selling author, speaker, & consultant on Leadership.

As a manager, there is always more to be done than what fits in your schedule. And while you may be keeping your to-do list updated, how can you make sure you’re prioritizing the right things every day?

Well, for starters, if you waste a lot of hours doing administrative things like updating Google Docs and Sheets or other rudimentary tasks that can be outsourced, you're not making the most of your time. 

In that case, you’re also not being a multiplier for the rest of your team , which is a key component of growing as a leader.

How do you value your time?

Think of it this way - if you earn $100,000 per year and work 50 hours a week for 50 weeks a year, your time is worth $40 per hour.

That means even a few hours a week spent on administrative work and repetitive tasks can lead to thousands of wasted dollars on something an app or an assistant can do for a fraction of the cost.

As a manager, you should always think of ways to maximize your own time as well as make sure your team is as productive as possible.

Having a mentor can go a long way in helping you do this - their experience can help you tell if you’re micromanaging or getting too caught up on things you shouldn’t really be doing.

They’ve been in your shoes so they can probably share systems and ideas for prioritizing your work well. They can also help you think about ways to be more productive and be a multiplier for your team.

To find out more about how to do that, you can ask them the following questions:

• What are some techniques I can use to better manage my time?
• How do I become better at prioritizing my responsibilities?
• What habits should I adopt to be a more effective leader? Which ones should I avoid?
• How can I organize my time to become a multiplier for my team?
• What are key actions I should take to help my team get more done?
• How do I know if a meeting is worthwhile, or I should cancel it? 
• How do I have effective meetings?
• When would you recommend we use asynchronous communication?

If you’re interested in more ways for prioritizing your time and being a multiplier for your team, check out these links:

• Why Priority Management Trumps Time Management - Lighthouse Case Studies
• Why Work-Life Balance Beats the Hustle Hype for Great Teams
• Your Guide to Synchronous vs. Asynchronous Communication
• 10 tips for conducting effective meetings
• Tips for remote management from a veteran

4. Questions about your career development

As a leader, you need to take charge of your own career growth. That usually means asking the right questions in your 1 on 1s with your manager to help open up your career to develop in a variety of ways.

As great as that sounds, it sometimes involves facing some hard truths. You may not always love what your manager has to say about your skills.

Despite that, you need to be brave and show initiative and a willingness to work on your weaknesses. And there’s nothing better to prepare you for that than talking to a mentor.

Your mentor will be able to share an objective opinion about your skills that isn’t influenced by company politics or team dynamics.

They’ll be able to tell exactly what you need to learn to take your career and skills to the next level. This way, you’ll know what to expect when you talk to your manager about career development in your 1:1s. You’ll be better prepared for difficult conversations and show your manager you take your own development seriously.

Try asking your mentor some of these questions to gain a better understanding of the skills you need to take things to the next level:

• What are the most important areas I need to master to get promoted to the role I want?
• What skills gaps do you think I have? 
• What are key habits you feel make someone successful in [your new role/ the role you want next]?
• What do you think it would it take for my manager to feel I'm ready for [desired role/promotion]?
• What do you feel are my strengths? How could those help the team more and help me advance in my career?
• How can I start to make progress on the areas I need to work on? 

If you need more resources on driving your own career growth, check out these posts:

• How Employees Can Drive Their Own Career Growth
• The 8 Best Professional Development Goals for Managers
• Career Development Plans: What Managers Struggle with Most
• How to Evolve Your 1-on-1s Over Time for Maximum Value

5. Questions about networking

While most of what you hear from your mentor will be based on their own experience, there’s another huge benefit you can gain through your relationship with them - their network.

As you build trust with them and ask more questions, they may not have all the answers themselves. Or, they may want you to hear other perspectives. Either way, it presents an opportunity for them to open their network to you. 

They’ll be able to introduce you to more people who’ve had a career path similar to yours, share professional events you could attend, and guide you on how to engage people more effectively and what to ask them.

Connections make the difference

In his book, “The Glass Bead Game” , Nobel prize winner Hermann Hesse explains the best way to gain knowledge is to build connections between your experiences. He notes how the best painters are usually avid readers or musicians, always looking to soak up new ideas from worlds other than their own. 

He also adds that these multi-disciplinarians have historically spent time together in artist cliques that grew into movements like impressionism, cubism, and others.

Similarly, when you expand your network, you’re giving yourself new perspectives and ideas. However, to truly be successful, you need to find the right people to meet.

A mentor can help you with that, as they’ve likely built a lot of professional relationships to get to where they are today. Use the time you spend with them to ask them how you can expand your network to accelerate your growth. You can ask one of the following questions:

• What events/conferences/meet-ups do you recommend for expanding my network?
• Who in your network do you think could help me grow as a manager? How can I help you make an introduction?
• What are some of the best online sources to find peers and exchange ideas with them?
• What are some good networking questions to ask to spark interesting conversations?
• How do you decide if an event is worth your time? 

By relying on your mentor’s experience, you’ll be taking a shortcut to the many relevant circles, events, and networks that can shape your leadership style and give you new opportunities to learn.

6. Questions to help you learn from your mentor’s career

Your mentor’s experience is unique. Even if you cover all of the areas we’ve mentioned today, there are still so many other things you can uniquely learn from them if you just ask.

Use the time you have together to build a deeper bond with them and find out about some of their personal experiences that have influenced them the most.

Even if they’re not directly applicable to you, they’ll likely help you see the bigger picture and understand the process of becoming a better manager. You’ll also understand how the steps in their careers influenced who they are today.

Here are some questions you can ask that focus specifically on your mentor’s career:

• What are some of the most important habits that have turned you into the manager you are today?
• What are the biggest mistakes you’ve learned from?
• Is there anything you wish you’d have done differently in your career? What would you change?
• Who are some of the most important people who influenced you and your way of thinking? What did you learn from them? 
• What are some unique things you did that set you apart from the others in your career?

Touching on their career specifically will allow you to complement what you learn through other questions in this post. It will help you better get to know them, and reveal unique insights about their life that you may want to repeat, or do differently. 

That’s what having a mentor is all about: shortening the time you need to get to career-changing knowledge and experience.

Unless you both have lots of free time, you’ll probably be seeing your mentor once a month (or less). To make the most of your time with them, ask them some of the questions we’ve prepared in this post and act on what you learn from them.

That might mean working on a particular soft skill, reading a new book, adopting a new outlook and mindset, meeting new people, or simply putting into practice what you talked about.

Whatever the area you focus on, make sure you set clear action items for yourself and follow through on what you discuss with your mentor.

It’s the only way to make your relationship with your mentor meaningful and valuable. It also is the most important thing to keep them as your mentor, because mentors want to see that their efforts with you are paying off. 

Learn something today? Share it so your friends can, too:

Jason Evanish

As the founder and CEO of Get Lighthouse, Inc , Jason and the Lighthouse team have helped managers grow their leadership skills in dozens of countries around the world. They’ve worked with a variety of companies from non-profits to high growth startups, and government organizations to well known, publicly traded companies. Jason has also been featured in publications including NPR, the Wall Street Journal, and Fast Company.

5 Critical Coaching Principles for Leaders to Learn

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50 Essential Questions to Ask a Mentor

Mentors can be invaluable resources for advice and guidance in our lives, whether we need help navigating difficult professional situations or looking for direction in achieving our personal goals. Finding the right mentor can be a challenge, but once you've identified someone who fits your needs, it can be incredibly helpful to have an expert to turn to. To ensure that your mentorship is beneficial to both parties, this article will discuss 50 essential questions to ask your mentor!

Preparing for Your First Mentorship Meeting

Setting clear goals is the first step to having a successful mentorship relationship. While you may have a general idea of what you'd like to gain from the relationship, it helps to document your individual goals and expectations before meeting with your mentor.

After setting goals for your mentorship, you'll need to find a good mentor who can help you achieve them. It's important to find someone who is experienced, knowledgeable, and willing to offer advice and guidance in your areas of interest.

Below, we share some great tips to help you find your first mentor:

1. Look for people with similar interests

Seek out individuals with shared experiences or interests you can relate to.

2. Research potential mentors

Before meeting with someone, read up on their background and accomplishments so you'll be better prepared for the conversation.

3. Ask your network

Reach out to professionals in your circle of contacts to see if they would be willing to mentor you.

4. Attend relevant conferences and events

Networking is a great way to meet potential mentors in person.

Once you've found a mentor, you'll need to prepare some questions to ask them. In the sections below, we share some great first questions to ask your mentor.

Getting to Know Your Mentor

Establishing rapport is an important part of any mentorship relationship. Asking your mentor questions about their background and experience can help you get to know them better while also helping them understand how they can best support your goals. Here is a list of questions to ask your mentor:

1. What inspired you to enter this field?

This question will help your mentor discuss their passions and motivations, which can provide valuable insights into their approach to mentoring.

2. How did you get to where you are today?

Asking this question is a great way for your mentor to discuss how they achieved success in their field.

3. What have been some of the biggest challenges you've faced?

Knowing the struggles and failures that your mentor has experienced can provide valuable lessons for you.

4. What do you enjoy most about your work?

Asking this question can help open up a more personal conversation with your mentor, which can help build trust between the two of you.

5. What professional skills have been the most helpful in your journey?

Knowing the skills that are essential for success in your mentor's field can help you understand what you need to do to succeed.

6. What advice would you give to someone starting out in this field?

This question is a great way for your mentor to share their best practices and wisdom with you.

Seeking Advice and Insights

As a mentee, you'll likely be looking to your mentor for advice and insights that will help you grow in your career and life. Here is a list of questions to ask your mentor about their experience and perspectives:

1. What advice would you give to someone facing a difficult professional situation?

Knowing how your mentor has handled challenging situations in the past can help provide valuable insights into your own.

2. How do you stay motivated and productive?

Asking this question will provide useful tips on staying focused and productive in your field.

3. What strategies have you used to build successful relationships?

Learning how to build successful professional relationships is a key skill for any mentor.

4. What have been the most important lessons you've learned from your mentors?

Mentors can learn just as much from their mentees, so this question can open up a dialogue about what they've learned in their own mentorship experiences.

5. What do you wish someone had told you when you were starting out?

This question can help your mentor reflect on what they wish they'd known when they began their career.

These are just some general questions you can ask regarding your mentor's experience and insights. Here are some more specific questions that you can ask to gain more targeted advice.

Business Strategy and Planning

Business strategy is just as important for small business owners as it is for big corporations. Asking your mentor about their strategies and plans can give you valuable insights into how to achieve success. Some great strategic questions to ask a mentor are:

1. What key factors should I consider when formulating a business plan?

As you move along your career path or entrepreneurial journey, having a solid business plan is essential. With a mentor, you can cut out a lot of guesswork and get their advice on key factors to consider.

2. How do you recommend identifying and evaluating potential business opportunities?

Knowing how to recognize and assess potential business opportunities can help you maximize your success.

3. What strategies do you suggest for effective goal setting and execution?

Setting and executing goals play a central role in the success of any business or individual. Asking your mentor this question will provide you with valuable advice on how to plan effectively and achieve success.

Marketing and Sales

In this highly competitive world, every professional should learn how to market themselves and their products or services. Asking your mentor about marketing and sales strategies can help you gain valuable insights into how to stand out from the crowd. Here are some specific questions to ask:

1. What do you think is the most efficient way to promote yourself or a product?

Knowing which methods work best for marketing and sales will give you an edge in this competitive world.

2. How do you approach market research and identifying target customers?

Market research and understanding your target customer base are essential components of any successful business. 

3. What marketing strategies have been successful for you in the past?

Asking your mentor this question will provide you with valuable insights into the strategies they have used to successfully market their product or service. 

4. Can you provide guidance on building a strong brand and effective sales strategies?

Developing a successful brand and creating effective sales strategies are essential for any business. 

Financial Management

Your finances are an important factor in achieving success, both personally and professionally. Discussing financial management with your mentor can help you understand how to maximize the success of your business. Here's a list of questions to ask:

1. How should I approach financial planning and budgeting for my business?

Most newcomers in an industry often find it challenging to plan and budget for their business. Asking this question can provide valuable insights for getting started on the right foot. 

2. What metrics or key performance indicators (KPIs) should I focus on?

There are various metrics and KPIs that can help you measure the success of your business. Some of the ones you should ask more about include profit and revenue, customer lifetime value (CLV), and customer acquisition cost (CAC). 

3. What advice do you have for raising capital and securing funding for a startup?

If you've ever tried to raise funds for a venture before, you know how difficult it can be. This question can provide useful insights into what financial strategies you should pursue in order to secure the resources you need. 

4. How do you make sure that your spending is in line with your goals?

This question is key to understanding how to ensure your spending aligns with your business goals. With the help of your mentor, you can learn strategies for staying on budget and investing wisely. 

Overcoming Challenges and Obstacles

At the start of your entrepreneurial or career journey, you're definitely going to face some challenges and obstacles . Asking your mentor about how they have handled difficulties in the past can provide you with valuable perspectives on how to overcome any sort of hurdle. Here are some questions to ask:

Dealing with Failure and Setbacks

1. what have been the most valuable lessons you've learned from your mistakes.

Understanding what you learn from mistakes and setbacks is essential for growth. Your mentor can provide great insights into how they've grown from their own missteps.

2. What advice do you have for bouncing back from failure and staying motivated?

There are times when it can be difficult to stay motivated and keep going. Your mentor's advice on how they overcame such situations can help you get back in the saddle. 

3. What strategies have you used to stay flexible and nimble when dealing with unexpected circumstances?

Unexpected events are a part of life, so knowing how to handle them is essential for success. Asking your mentor this question can help you stay prepared for any eventuality.

4. Can you share a specific example of how you turned a challenging situation into an opportunity?

Knowing what specific challenges to expect in your industry can be incredibly helpful. With this, you can steer clear of potential pitfalls and capitalize on opportunities. 

Balancing Work and Personal Life

Let's face it: the lines between personal life and work can become blurred, especially when you're starting out in a new venture. Your mentor has probably faced this situation before and can give you valuable advice on how to manage work-life balance. Here are a few mentorship questions to ask:

1. How do you manage work-life balance as an entrepreneur?

This is a key question to ask your mentor, as they can provide invaluable advice on how to juggle work and personal life.

2. What strategies do you suggest for setting boundaries between work and home?

Setting boundaries between working time and leisure time can be difficult. Your mentor's advice on this matter will help you keep your sanity in check.

3. How do you handle stress and avoid burnout in your entrepreneurial journey?

Burnout is a terrible thing to experience and can have dire repercussions for your business. Asking your mentor how they manage stress and avoid burnout will help you stay energized. 

Career and Self Development

Continuous progression and self-development are essential for success. Below, we share some questions to ask your mentor about career development and success.

1. What books, courses, or other resources have been most useful in helping you develop as a professional?

Knowing what sources of knowledge to explore can be immensely helpful. Asking this question can provide some great ideas for self-development.

2. Do you think I am on the right track and making progress?

Routinely asking questions like this will help you stay on track and identify areas for improvement. 

3. Am I communicating enough with you?

If you feel like you're not getting enough guidance from your mentor, it's important to let them know and ask for more feedback. 

4. Do you have any advice on how I can best utilize my time and resources?

Knowing how to use your available time and resources most effectively is key to success.

5. Is there any other way you think we could communicate more effectively?

Effective communication is essential for a successful mentor-mentee relationship. Asking your mentor this question will help you ensure that you are both on the same page and making progress. 

6. How do I become better at negotiating?

Negotiation is a key skill required in any business. Some common questions to ask your mentor include: What tactics have you used for successful negotiations? What strategies do you use when faced with a difficult negotiation? And how do you ensure that both parties come away from the negotiation feeling satisfied? 

7. What do you think are the most important traits of a successful entrepreneur?

Asking this question can provide invaluable insights into how to develop yourself as an entrepreneur. Your mentor's answers will be very useful for your own growth and development.

As you progress in your career, you'll be given more responsibility and will have to make decisions that can affect your team. Here are some of the best questions to ask a mentor about how they handle leading a team:

1. What strategies do you use for creating an effective team culture?

A successful team needs strong leadership and a supportive environment. A mentor would have great insights into how to foster these qualities in a team.

2. What techniques do you employ for motivating and inspiring your team?

A motivated team is essential for success, so it's worth consulting your mentor on the best ways to motivate them.

3. How do you handle disagreements between members of your team?

Understanding how to deal with conflicts is an important skill for any aspiring leader. Asking your mentor about this can help you avoid potential issues in the future.

4. How do you ensure that everyone on your team is engaged and productive?

Keeping the whole team focused and productive is an important part of leading a successful venture. Consulting your mentor on how they handle such situations will be incredibly useful.

5. What qualities do you look for in a successful team member?

Knowing what traits to look for when building your team is essential. Your mentor's advice on this matter can help you pick the right people for the job.

6. How do you handle difficult conversations and give constructive feedback?

Being able to give constructive feedback is an important skill for any leader. Asking your mentor about how they handle such conversations can give you valuable insight into the best practices.

7. What was your worst leadership decision?

Leadership can be a tricky path to navigate, and mistakes are inevitable. However, learning from other people's errors can help you stay ahead of the curve.

Career Paths

1. what are the first steps to changing a career.

Sometimes, you may want to make a career switch. This may be due to a change in interests or simply because you are looking for new challenges. Consulting your mentor about their experience with career changes can provide valuable advice on how to make the switch as seamlessly as possible.

2. How can I combine my interests or passions at work?

Combining your passions with work can be incredibly fulfilling. Your mentor's advice on how to do this will help you make the most of the opportunities available to you.

3. How do I transition into a management role?

Moving into a management role is an exciting step for any entrepreneur, but it also requires a lot of skill and experience. So you should probably ask your mentor about their experience transitioning into a managerial role.

4. How do I develop my network and get the most out of it?

Having a strong network is essential for career progression, so asking questions about how to build and use that network can be extremely beneficial.

5. What do you think are the key qualities of successful leaders?

Knowing what qualities to possess in order to become a successful leader is invaluable advice, particularly for those aspiring to move up the ladder. Your mentor's experience and insights here will be immensely useful.

6. How can I become more proactive about my career path?

Proactivity is key to career progression. Asking your mentor about their own experiences in this regard can provide some great advice for you to follow.

7. How can I incorporate meaning into my career?

This is a good career path question to ask your mentor. Seeking out meaningful work is important for any professional. Consulting your mentor about their own experiences in this area can be hugely beneficial.

Having a mentor is an invaluable asset that can help you progress in your career. And so far, we've discussed 50 questions to ask a mentor. With these questions, you'll be well-prepared to make the most of your mentorship and gain valuable knowledge from your mentor. All that's left now is to ask away!

Remember to reflect on what your mentor tells you and use it to help guide you in your entrepreneurial journey. Also, make sure to thank them for taking time out of their day to help you grow as a professional. Your appreciation will go a long way! Plus, don't forget to keep up with your mentor by sending regular updates and maintaining open communication.

Frequently Asked Questions

1. how to ask for mentorship.

Asking for mentorship can be intimidating, especially if you are new to the field. Remember to make your request as specific as possible and provide an overview of what you hope to gain from the relationship. If appropriate, offer something in exchange, such as help with their own work,

2. What Are The Benefits Of Having A Mentor?

Mentors provide invaluable advice and insights that can help you grow both professionally and personally. They can be a trusted source of support, encouragement, and guidance as you progress in your career. Additionally, having a mentor often gives you access to increased opportunities and resources.

3. How Often Should You Meet With Your Mentor?

This depends on the type of mentorship you have established, but generally, it is recommended to meet with your mentor at least once a month. It is also important to keep communication open between meetings, as this will help strengthen your relationship.

4. What Are Some Good Mentee Questions?

It is important to ask your mentee the right questions so that you can better understand their goals and how you can help them achieve them. Some good questions to ask are:

• What do you want to accomplish in the next year?

• What resources or tools do you need to get there?

• What key skills would benefit your professional growth?

• What do you want to learn most from this mentorship?

• How can I help you reach your goals?

Alex Quin is a full-stack marketing expert and global keynote speaker. Founder and Chief Marketing Officer of UADV Marketing - a member of the Forbes Agency Council.

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75+ Great Questions to Ask Your Mentor (The Ultimate List)

Did you find a great mentor, but you don’t know what to ask them?

Here are some good questions you might want to consider:

Hannah Gentile

Entrepreneur | Mindset Coach

“What was the process you used to find your ‘why’?”

This tells you a lot about how your mentor approaches meaning and purpose. You could take something from their process.

“Have you seen other processes of finding your ‘why’ you found interesting?”

Just because a technique doesn’t work for your mentor, doesn’t mean it won’t work for you. Good mentors will have collected tips from others which they will be able to share with you. It is like having a group of mentors!

“What values drive you?”

It is handy to know you have some cross-over or similarity in driving factors. It is also nice to have differences. Differences allow you to reflect on the strengths and limitations of your own values, and ways to balance that out.

“How do you approach risks?”

A personal favorite. You probably don’t want someone who is overly cavalier helping you out! But neither do you want someone so adverse to risk that you can never take action. Approach to me is a fascinating insight into how someone calculates, mitigates, and acts upon, risk.

“Do you have a goal-setting process you believe in?”

Not everyone likes the idea of goals. Have a think about whether you want a mentor who can suggest a solid structure for your goals, or whether you want to be introduced to a different approach entirely.

“What has been your biggest failure / what did you learn from it?”

There is no hiding from the fact that we learn more from failure than success (although success is an important learning tool too). Many an amazing Phoenix has been born from the most heartbreaking of ashes. You don’t want your mentor learning from your failure…so find out where they’ve gone before you and how you can avoid the same mistakes.

“What has been your biggest challenge? How did you approach it?”

To be honest, the challenge is less important than the approach. Most challenges can be faced in similar ways – to find out what process your mentor has for tackling those tough times.

“What has been the most valuable lesson you’ve learned?”

Another favorite. Every person you meet knows something you don’t. Your job is to find out what that thing is. Your mentor has hopefully built up a treasure trove of these little nuggets. Start digging.

“What is one thing you wish you would have done, that you didn’t?”

A survey of people close to death found that one of the biggest regrets people had, was not what they’d done…but what they had missed out on doing. The risks they did not take, the paths they did not go down.

What is something your mentor wished they had taken up? How can you make this relevant to you?

“What is something you thought was important but has turned out not to be?”

All too often we get caught in a rabbit hole of the one thing you must do to make millions. Or to be a success at ‘this’ or ‘that’. You can avoid all that time and energy but finding out what your Mentor spent unnecessary time on.

Matt Edstrom

CMO, GoodLife Home Loans

“Has there ever been an instance in your career where you felt like you weren’t successful? How do you rebound from failure?”

Inquiring about past instances of failure with your mentor can be a great technique for establishing a good rapport.

It’s a great question because it leaves ample room for an open-ended response, which is a great way to break the ice with someone you may not yet be comfortable approaching & chatting with.

By inquiring about something pertaining to their career, you are demonstrating an interest in them. The question appeals to the notion that most people enjoy speaking about themselves, and if you can somehow tie the question into something that directly pertains to their career, it can further benefit you if you ever come across a similar problem during the course of your career.

You could even follow up the question by asking about an instance where they felt most successful if you’re trying to find a balance, and not focus solely on their past failure(s).

The takeaway is that asking a question that can be answered in story form is a great way to encourage a mentor to talk about themselves.

Related: Overcoming Fear of Failure (Avoid these 3 Mistakes)

“I tried to execute a task and it didn’t go as planned. Could you perhaps help me identify where I went wrong, and how to avoid the issue in the future?”

Being able to approach your mentor about things that went wrong for you when trying to execute something at work is essential for learning & growth. It shows that you are not only comfortable enough to approach them with an issue rather than hoping it will take care of itself if ignored, but also that you trust your mentor to the point where you want to heed their advice.

Demonstrating transparency is a trait that should not be ignored. Being able to show you value your mentor’s opinion builds the bond and trust in the relationship.

There is also a lot to be said about possessing a strong sense of self-awareness rather than deflecting, which demonstrates your ability to recognize when you did something incorrectly in the first place. Having that self-awareness enables you to more easily recognize when you need to reach out for assistance.

“What types of skills should I be aiming to hone in on?”

Asking about building up skills that pertain to the job shows your mentor that you strive to improve your skills to become a better employee.

This helps notify your mentor that you are serious about wanting to grow rather than just complete the bare minimum. Most of the time, your mentor will start providing resources for you that relate to whatever skills they said would be wise to improve.

These resources can serve as incredibly valuable, and can potentially carry over to other jobs in the future. The tenacity to learn more is a common trait among those in leadership roles. By demonstrating that sense of tenacity, it may cause your mentor to consider you for leadership roles down the road.

Jason Patel

Founder, Transizion

“What was your biggest failure and how did you overcome it?”

Learning from failure is the hallmark of greatness. You want to know what high-performing people went through and how they overcame their challenges. Perhaps you can take struggles from their life, relate them to your own journey, and apply their solutions. Learning from others’ mistakes is a great way to minimize your own and save time.

“Do you recommend graduate school?”

Some of us are destined for graduate school, while others are not. Your mentor can show you the way and give you feedback on whether your professional path necessitates graduate school. A good response from your mentor can have you applying to graduate school soon or saving your money altogether.

Yaniv Masjedi

CMO,  Nextiva

Here are a few of my top questions for a mentor:

• “If you could do it all over again, would you change anything? If so, why?”
• “What are you most proud of?”
• “What were your goals at the start of your career?”
• “What would you do if you were me?”
• “Did you ever land a role that you weren’t fully qualified for? How did you prepare yourself?”
• “How did you become such a good public speaker?”

The questions you ask your mentor will depend on where you and your mentor are at in your respective careers, and what each of you aims to get out of your relationship. The above questions should be useful to an early stage professional paired with a senior executive.

Mentorship can provide one with answers to both personal and philosophical questions, as well as practical how-tos for gaining new skills and overcoming challenges.

Larry Sternberg

Immediate Past President, Talent Plus, Inc.

The questions to ask your mentor will inevitably shift over time as both your mentoring relationship and your situation evolve. Here are a couple of questions you can ask near the beginning of the relationship (when you might not yet apply the term “mentoring”).

Ask these questions in your own words and style. It’s the concept that’s important, not the precise words.

• Tell me about some of your mentors.
• What can I do to ensure that you feel this is a valuable use of your time?

I am aware the following are not questions, but here is some advice to get the most out of your relationship with your mentor.

• Implement his or her advice. Otherwise, your mentor will become disengaged. As my wife says, “Don’t buy a dog and bark yourself.”
• Come prepared with issues/questions to discuss, so that you can make the best use of your time.
• Don’t just bring problems. Celebrate successes, too.

Angela Connor

Founder and CEO, Change Agent Communications

Ask your mentor the things no one is going to teach you – about incorporating who you are outside of corporate America, into a space that doesn’t always embrace the unfamiliar, unique or what may seem different or “out-of-place” in the work environment.

I had to learn on my own how to bring all of who I am so to speak into the work environment as I climbed the ladder and moved into senior and ultimately executive roles. If someone had told me sooner that my authenticity and (a girl from Detroit attitude) is what made me personable, relatable and human in an industry where relationships matter and chemistry is important, I may not have been as hesitant early on. Too many times we hide some of who we are thinking we need to be two different people, especially African-American women.

No one wants a robot, so if you don’t inject personality and never reveal anything about you that sets you apart, you can’t win as big.

It’s important to develop enough trust with a mentor to touch on those emotional pieces and not be so fixated on how to get promoted, or how they can be a sponsor to connect you to the right people. 

With teen daughters, I’ve seen how dependent they are on technology for relationships, so I make them do what’s uncomfortable. I don’t always let them order food online or through an app for instance. That’s small, but I make sure they are talking to people face-to-face.

I believe that Gen-Z is going to need more mentoring on interpersonal relationships, so those are some of the things that will have to be covered as well – talking about being present and connected in an increasingly connected, yet disconnected world.

Paige Arnof-Fenn

Founder & CEO, Mavens & Moguls

• “What was your path?”
• “How did you know it was right for you? Would you choose it again today?”
• “What has been your best and worst job?”
• “What has been your best worst boss?”
• “Do you have any career regrets?”
• “Is there ever a life balance?”
• “What is your biggest source of pride and joy?”
• “How have you recovered from failure?”
• “What do you do for fun?”
• “What is your favorite quote?”
• “What is your favorite movie?”
• “What is your favorite book?”

Brad Ormsby

Owner, Colorstone Marketing

One of my favorite questions to ask my mentor is how they arrived at a certain idea. Written another way, how do you think about this situation?

My mentor is successful in business and a serial entrepreneur. And one of the things that fascinate me is how he identifies opportunities I never would have thought about. But I want to figure out how he thinks about things.

His patterns, how he fuses ideas together, and how he spots trends. Instead of finding out about a specific situation, I want to train my mind to think this way.

So I ask about the mental process that led to that decision rather than the decision itself. I think it’s important to learn to think like your mentor (assuming they’re living the life you want) so you can eventually become the mentor and pay it forward.

Dayne Shuda

Owner, Ghost Blog Writers

I find that mentors often give advice that is counter to their own journey to success. One example I’ve often heard from successful people is that they wished they would have gotten their college degree.

So when I’m chatting with a mentor or someone that’s successful I like to ask them their experiences and then pull my own lessons from their stories.

It might start with a question like, “What was the first year like?”

Then it might get into, “What helped get you to the next level?”

And then I’ll throw in, “What was a big challenge at that point and how did you respond?”

There are all kinds of questions you can ask, but the key is to focus on their story and pulling your own lessons from that story. Focus more on the actions they actually took over what they suggest or tell you that you should do.

Dane Kolbaba

Co-Founder, Watchdog Pest Control

Things they realize in hindsight. For any big decisions, they’ve made throughout the years, for the bad and perhaps the not-so-bad choices they’ve made.

This would give me a better idea of what to expect for any similar decisions I’d be needing to make in the future, for what possible reward and fallout there would be.

What they could tell their younger self , for each milestone of their adult life . We tend to be so consumed with our own lives — what we need to do, what we want to do, where we need to go, where we want to go — that we neglect to stop and think about what it is we’re really doing and why.

I have plenty of things I wish I could have told my younger self, and a mentor who’s further along in life would no doubt have invaluable insight.

Their biggest regret professionally, and if they’d share it, even personally. Something they did but wished they could undo or take back, but more importantly, something they wish they did do but lacked the courage to do so.

Rachel Richards

Finance Analyst | Founder, Money Honey | Author, Money Honey

In my experience, it’s best to ask your mentor questions that stand out. Stay away from the overly-used and too-broad “What’s the best career advice you can give me?” or “What are your best management practices?” Questions this vague are difficult to answer.

Try one of these instead:

• “Was there a clear turning point in your career? What happened and how did you navigate it?”
• “What’s one of the most challenging conversations you remember having?”
• “What suggestions do you have for asking for feedback from my peers and bosses?”
• “What do you see as my areas of improvement ?”

Also, ask them about themselves. As Dale Carnegie once said, “To be interesting, be interested.” Your mentor will be more partial to and open with you if you ask them personal questions about their background and successes.

Try one of these:

• “What was a trying time for you in your career and how did you overcome it?”
• “You make it look so easy. What aspect of your career was more challenging than most people realize?”
• “What do you wish you’d known 15 years ago?”
• “What one decision have you made that has impacted your career the most?”

Operations Manager, My Trading Skills

I would focus my questions on my mentor’s failures throughout their lives, and how they ended up getting back up after these setbacks. As such, some of my questions would be:

• “What has been your biggest failure to date, and what effect did it have on you, your goals, your vision, and your future decisions?”
• “Which are the biggest lessons did you learn from this failure, and how have you implemented these lessons?”
• “How did you get back up after this major setback? Did you ask for help?”

Bottom Line: Learning from your mentor’s failures will help you prepare for and possibly avoid major pitfalls on your journey.

VP of E-Commerce & General Manager, CanvasPeople

“What do you wish you had asked somebody earlier?”

This question will open up an extremely valuable conversation about self-awareness, growth, and vulnerability. A good mentor exemplifies all three of those things. You not only want to learn from your mentor’s successes but from their failures and things they wish they had done differently. A lesson that many entrepreneurs need to learn is that it is ok to ask for help, and any good mentor will be able to tell you that.

Stacey Berk

Managing Consultant, Expand HR Consulting

• “At this stage in your career, how did you learn one of the following… to plan more strategically, make better decisions, focus on time management, and build improved relationships with people?”
• “At this stage in your career, how did you learn to lead people? As a leader, how did you recruit, develop and retain your staff?”
• “What do you think have been my core strengths as you have watched me grow over the years professionally?”
• “What do you think I should focus on for the next 3-5 years to get to the next level in my career?”
• “What resources do you think I need to achieve those areas of focus?”

Varda Meyers Epstein

Parenting Expert and Writer, Kars4Kids

I think the question every mentee should ask a mentor is: “How do you keep a positive attitude when things are going against you?”

This is what every mentee really wants to know because it is very easy to get depressed when things are stacked against you. Often, that’s exactly the case with a mentee, who generally needs mentoring because s/he may not have a supportive family or comes from a low-income neighborhood. It’s usually why they need mentors in the first place.

It’s easy to think: why to get good grades in school, stay out of trouble, go to college, look for a job when you’re stuck in a vicious cycle. It can feel like you work twice as hard as everyone else, but you just don’t get ahead.

The thoughtful mentor understands that what he’s being asked for is hope, and a way forward, too. The response doesn’t have to contain the wisdom of the ages. But it does have to give the mentee something to hold onto, or a step to take in a positive direction.

Stacy Caprio

Business Coach | Growth Expert

I’ve found it helpful to ask mentors what their biggest failures have been and to hear their stories and answers in depth.

You already know your mentor has done some admirable things and maybe they have even helped or taught you to do the same.

Learning about their mistakes and the ways they have been hit hard by external circumstances or their own failures is a huge benefit you can lean on them for since learning what has gone wrong for them will often save you from going through the same negative experience yourself.

Lily Ugbaja

Founder, FindingBalance.Mom

The top question everyone should ask their mentor is “If you could start over, what would you do differently?”

I’ve found this question helps uncover common mistakes and major pitfalls to avoid, effectively speeding up your journey to success by at least 50%.

Most of the time we spend building is actually spent on trying stuff and failing at them. So I use this question to eliminate a lot of “smart” fail and get a leg up! Plus it seems to be an easy one for mentors to answer thoroughly.

Matthew W. Burr

Human Resources Consultant, Burr Consulting, LLC

“Where do you see my strengths and weaknesses, how can I improve?”

The mentor should focus on all area’s in an individual. What they do well, and where they need to improve. With concrete examples of both and a path to success. Here are recommendations to improve x, y, z.

“What opportunities will best help in my personal, professional and emotional growth?”

This one is going to be more personalized, the mentor should focus on what the person wants to accomplish and put a joint plan together to ensure there are agreement and accountability.

Megan Meade

Marketing Specialist, Software Path

As a woman in business, it’s extremely important to have a mentor who can lift you up and encourage you to grow. A mentor relationship provides opportunities to advance, as well as builds confidence and reduces the prevalence of ‘impostor syndrome’ which a lot of women fall subject to.

An outside perspective improves women’s objective viewpoint of their own skill level and can reduce hesitancy about reaching for higher career goals. You and your mentor need to understand each other’s inner workings to achieve the full benefits of your relationship. One way to do this is by asking lots of questions.

One of the most important questions to ask your mentor is: “How do I measure my success against my goals?” This is a great way to ensure you and your mentor are on the same page when moving forward; the picture of what is ‘success’ looks different for each person.

It’s essential that you and your mentor are measuring progress in the same way otherwise there will be a disconnect in what that looks like. This is also important for personal goals or seemingly non-quantifiable goals, as it opens up a metric to hold yourself to and that your mentor can use to actively help you.

For example, if you have a personal goal of being more assertive at work, this would be hard to measure beyond a general ‘I think I’ve been more assertive’, but if you add a few metrics e.g. I will send out three meetings invites this week, I won’t reschedule other commitments around another person’s schedule, and I will not use mitigating language such as ‘just’ when writing an email asking someone to do a task. You can later revisit these metrics and see how you’ve performed, and then look at the impact of this with your mentor.

Success, in this scenario, may be targeted as scheduling the planned meetings, only adjusting other commitments once in a month, and only using ‘just’ 4 times in email exchanges over the whole month. This way, even if one target isn’t achieved, it’s likely there are small successes within the overall goal too.

Asking what success looks like also enables you to understand your mentor’s thought process. What seems a success to them, may not have occurred to you at all – which helps them help you to see things through a different perspective.

This is especially important in a business setting, a business mentor may set a goal and success measure you’d never thought of which encourages you to broaden your skill set and grow – which is what mentorship is all about!

Related: 22 Reasons Why Goal Setting Is Important for Success

Bernice Quek

Head Writer, Bumble Scoop

In my opinion, it’s essential to form a personal relationship with your mentor. Having a mentor should go beyond just sharing tips and tricks about navigating through your career; he/she should also be a figurehead that inspires you to become a better person.

A great question to ask would be “What made you who you are today?” .

This gives you an insight to your mentor’s journey to becoming the person and worker he is today. It may open emotional doors that you never knew existed, or show you that while he’s successful, he is also human.

The way to build a closer bond is when all emotions are on the table. Only when your mentor opens himself up to you, then the two of you will have a stronger connection.

In the days ahead, you’ll always remember the heart-tugging story he shared to fuel you through any obstacle. A tighter bond will also mean better chemistry and the possibility of a mentorship turning into a treasured friendship. This will only translate to positive changes in your mindset and attitude towards both work and life.

Rishit Shah

Founder, TallySchool

• “What is life?”
• “Why do we do what we do?”
• “Why are we doing so many things when ultimately we all are going to die?”

I have asked these questions to my mentor.

When we are living, it is natural to ask a question of what is life. What is the meaning of life?

Most of the people are doing a job or business just to earn money. But, when our survival is taken care of, we have these questions and we really don’t ask these kinds of questions to anyone including the mentor.

We should ask our mentor as to why we are doing, whatever we are doing. What is the purpose of it?

Related: What Is the Point of Life?

When we get a purpose, we can work towards it full-fledged with all our efforts in a single direction. Without a purpose, we cannot give our 100% to any task. We just do it for the sake of doing it. With a purpose, we know something better is going to happen and we are a part of it. This gives us a tremendous motivation to work towards our goal.

We should also ask the question of death to our mentor. It sounds frightening but we know we all are going to die one day. So why we are doing everything because we are ultimately leaving all this behind. We cannot carry anything with us after we fall dead.

This is a crucial question and a true mentor will give you the right answer. This answer is different for everyone. For someone, it can be to live a good life so he or she can die peacefully. For someone else, it can be a totally different reason.

The point here is to ask your mentor the above existential questions because these are the fundamental questions of your life and when these are answered, you will realize that a lot of burdens will be off your head and you can grow in life with full speed.

Monica Rivera

Producer & Podcast Host, You Wanna Do What?

Mentorship has been one of my most significant gifts and is a valuable, untapped resource for too many people. I like to think of my mentors as sources of tough love and sounding boards for new ideas and advice. The cornerstone of these relationships is honesty.

Use the time with your mentors to ask questions and receive answers that will challenge you and grow you.

I recommend the following questions:

• “What are my strengths? Are there any areas where I’m highly competent?”
• “How can I leverage my strengths in my current role or in seeking a new opportunity?”
• “Is there any place I’m falling short? What can I do differently?”
• “What’s the best advice your mentors have given you?”
• “How do I cultivate relationships in a sincere, meaningful way?”

Frequently Asked Questions

How do i find a mentor.

When looking for a mentor, it’s essential to consider the following factors:

Network:  Look within your existing network for people you admire and respect, who are successful in the field you’re interested in, or who have a wealth of experience you’d like to tap into.

Online resources:  Utilize online tools such as LinkedIn or professional associations to connect with potential mentors.

Industry events:  Attend events in your field to meet and network with others, including potential mentors.

Be proactive:  Don’t wait for a mentor to come to you, be proactive and reach out to those you admire.

Be open-minded: Be open to the idea of entering into a mentoring relationship and be willing to learn and grow from your mentor.

Finding a mentor can be a great way to grow professionally and personally. Still, it requires effort and determination on your part. Feel free to reach out to someone you admire and express your interest in mentorship.

It’s important to remember that only some mentors will be a perfect fit for you. Still, with persistence and patience, you can find someone who can guide you on your career path.

Can I Have Multiple Mentors at Once?

Yes. Multiple mentors can give you different perspectives, experiences, and expertise. For example, you could have one mentor who is an expert in a particular aspect of your career, such as a specific skill set, and another who has more experience with general career development and management.

However, it’s important to consider the time and resources required to maintain multiple mentoring relationships and the potential challenges of juggling multiple schedules and goals. You should ensure you can invest in each relationship and make the most of each mentoring opportunity.

What Should I Do if My Mentor and I Aren’t a Good Match?

If you feel that you and your mentor aren’t clicking, don’t worry – it happens to the best of us. The most important thing in this situation is to take ownership of the issue and find a solution .

Start by having an open and honest conversation with your mentor, expressing your concerns, and trying to find a way to make the relationship work. If that’s not possible, don’t be afraid to look for a new mentor who is a better fit for you.

Remember that your relationship with your mentor is crucial to your professional and personal development. So be proactive, communicate openly, and keep looking until you find someone to help you achieve your goals.

How Often Should I Meet With My Mentor?

Meeting with your mentor comes down to finding a balance that works for both of you. Here are some factors you should consider:

Schedules:  Both your and your mentor’s schedules play a significant role in determining the frequency of your meetings. Consider any conflicting commitments and find a time that works well for both of you.

Nature of your relationship:  The nature of your mentoring relationship can also affect the frequency of your meetings. Some mentors prefer a more hands-on approach and want to meet more frequently, while others prefer a more relaxed schedule.

Goals:  Think about what you want to accomplish with your mentorship. If you have specific goals in mind, you should schedule more frequent meetings to ensure you’re making progress and getting the support you need.

Availability:  Be flexible and adjust your schedule as needed to accommodate your mentor’s availability. If a busy time is coming up, you may need to adjust your schedule to ensure you can still meet.

How Can I Communicate My Goals and Expectations Effectively to My Mentor?

It’s important to be clear and concise about your goals and expectations when communicating with your mentor. Start by:

• outlining your overall career goals • then, get specific about what you hope to achieve through your mentoring • being clear about your priorities and what you expect from your mentor, such as specific guidance or feedback • set measurable goals for your mentoring relationship • check in regularly to ensure you’re on track

Good communication is vital to a productive and valuable mentorship. Ensure you’re open, honest, and clear in your conversations with your mentor.

What if I’m Not Sure What I Want to Achieve From My Mentorship?

It’s normal to be unsure of what you want to accomplish with mentoring, especially if you’re at the beginning of your career or exploring new ground. However, it’s important to have clarity and focus to make the most of your mentoring.

Start by thinking about your overall career goals and what areas you’d like to develop. Then, consider what particular skills or knowledge you’d like to acquire. You can also reflect on challenges you’ve faced in your career and how a mentor can help you overcome them.

Once you have a clearer idea of your goals, you can use them as a starting point for your conversations with your mentor.

How Can I Ensure That My Mentoring Relationship Remains Productive and Valuable Over the Long Term?

A productive and valuable mentoring relationship is vital to your personal and professional growth. Below are some ways you can ensure that your mentoring relationship remains strong and effective over the long term:

Communicate regularly:  Keep your mentor informed of your goals, expectations, and progress. This will help you align your mentor’s expectations with your own and ensure you’re on the right track. Don’t be afraid to ask questions or ask for clarification on points you’re unsure about.

Active learning:  Take the initiative to learn as much as you can from your mentor. Ask for feedback and guidance, and actively seek new opportunities for growth and development.

Prepare:  Make the most of each mentorship meeting by preparing questions, taking notes, and following up on action items. This shows your mentor that you’re committed to your development and value their time and expertise.

Two-way street:  Remember, a mentoring relationship is two-way. Be a supportive mentee by contributing to the relationship and appreciating your mentor’s time and guidance.

What Can I Offer My Mentor in Return for Their Guidance and Support?

Mentors often offer their guidance and support as a way to give back and support the next generation. However, it’s important to remember that mentorship is a two-way street, and you can also offer value to your mentor .

This includes staying in touch with your mentor and keeping them updated on your progress, contributing your own insights and perspectives, and being a supportive and engaged mentee.

You can also think about supporting your mentor’s professional goals, such as connecting them with other professionals in your network or helping them with projects.

By being a valuable and supportive mentee, you can strengthen your mentoring relationship and make the most of this valuable opportunity.

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The Editors

49 Questions To Ask a Mentor

Updated: March 11, 2024

Published: June 12, 2023

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. And in that first chat, you want to come prepared with strong, interesting questions to ask a mentor to set yourself up for success.

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.

Table of contents:

How to prepare for a meeting with your mentor

• Good questions to ask a mentor
• Strategic questions to ask a mentor
• Questions to ask a mentor at work

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. You can make note of the following, for example:

• Prior work experience: What about their professional journey is interesting or relevant to yours?
• Featured projects: Does any of their featured work or projects impress or intrigue you?
• Skills: Do you have any questions about how this person learned certain skills?
• Posts: Have they posted anything recently that resonates with you?

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.

When asking questions, especially in a virtual setting, remember to speak with enthusiasm. You can try out the following tactics to demonstrate your excitement and interest in your mentor:

• Speak louder than normal
• Change your intonation by raising and lowering your voice
• Maintain eye contact, either by looking at their eyes in person or directly at the camera
• Nod to show active listening
• Engage with their responses, asking follow-up questions and offering your own comments
• Keep your posture up

End the conversation with excitement, thanking them for their time and asking to set up another meeting in the future.

Good Questions To Ask a Mentor

At Your First Meeting

During your first chat with your mentor, you want to establish a rapport and learn more about them.

Start by engaging with them on how they’re doing, providing more than just “good” or “great” in response. Offer responses that create a natural transition into questions, such as:

• “I’m doing great — I’ve been looking forward to meeting with you since we first connected!”
• “I’m good, the weather is beautiful today. You’re based here as well, right?”
• “I’m feeling relaxed, my team just finished a big project.”

These responses start the conversation on a positive note, and gives your mentor an opportunity to ask follow-up questions about your day, project, or work. Afterward, you can start asking typical first-day questions.

Consider asking some of the following questions for 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?

About Work-Life Balance

Climbing the career ladder means figuring out what a healthy work-life balance means for you. Ideally, your mentor has mastered this art, and can offer tips and tricks that help ensure you stay 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?

Strategic Questions To Ask a Mentor

Besides more general inquiries, ask strategic questions about their career and leadership experience. You can use their answers to help your own professional trajectory, incorporating their tips into how you handle leadership and your career.

About Careers

Often, you seek out a mentor to get career advice and guidance. Try to tailor your inquiries to both your career and theirs. Consider asking some of the following to get 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?

About Leadership

Try to find a mentor who possesses strong leadership skills . As you progress in your career, you will likely find yourself taking on more managerial responsibilities. Having a mentor who has mastered leadership 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 at Work

Your workplace might assign a mentor when you first start — 84% of Fortune 500 companies offer mentorship programs. Unlike external mentors, you can tailor your questions to your mentor’s experience and trajectory within the company.

A few sample questions to consider:

• How did you end up joining this company?
• How does this workplace compare to your previous employers?
• What did you wish you knew when you first started?
• What company resources (e.g., learning materials) should I take advantage of?
• Who else can I meet with in the company for mentorship?
• What can I do to hit the ground running?
• How can I best support my team and the organization?
• Why have you stayed with the company?
• Where do you see the company going in five years?

Remember: Mentorship benefits both the mentor and the mentee. 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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