70 questions to ask a mentor for a great mentorship experience

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.

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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?

Leadership

• 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

1. Where do you think my strengths lie in?
2. How can I develop the right discipline to achieve my goals in this industry?
3. What are the necessary skills that I should develop to rapidly grow in my career?
4. What are some things in your career that you regret not having done earlier?
5. How do I effectively manage my time and prioritize accordingly?

Stories

1. Do you even get impostor syndrome? How did you learn to get over it?
2. Did you have a hard time starting out in this industry?
3. What are some hard choices that you made to get where you are in your career?
4. Did you experience some major setbacks in your business/career path? How did you bounce back?
5. What are some instances that you would have done differently?

Situational

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

Accountability

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

Career growth and development

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

Situational questions to ask a work mentor

1. My boss always shuts me down in meetings. What’s the best way to respond when it happens?
2. 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?
3. 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?
4. 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?
5. I feel as though my current role suffocates my creativity. How do you think I can make the situation better?
6. I’m constantly having to complete or re-do my coworker’s work. What should I do?
7. 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:

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

Questions to ask a cyber security mentor

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

Questions to ask a project manager mentor

1. What knowledge, skills, and abilities are required for project management competency?
2. How do you get started with a new project and set it up for success?
3. What is more important to a project’s success, the project manager’s soft or hard skills?
4. How do I stand out from my peers? What qualities do you think I need to develop?
5. How can I be a more strategic project manager?
6. What strategies have you found successful in project management?
7. What techniques do you recommend for managing stress?

Leadership

1. What leaders do you look up to for inspiration?
2. What are some books you can recommend on leadership?
3. How do you keep your team motivated?
4. What qualities are lacking among today’s leaders?
5. 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:

1. What was your worst leadership decision?
2. What was the worst conflict you had to resolve?
3. What was the biggest leadership risk you took?
4. What was your proudest moment as a leader?
5. What are your current goals as a leader?

Entrepreneurship and business

1. What do you enjoy most about entrepreneurship? What is hardest about it?
2. What are some mistakes you wish you could have avoided?
3. What advice would you give to newbie entrepreneurs?
4. How do you brainstorm and finalize business ideas?
5. What are the biggest mistakes first-time entrepreneurs can make?
6. How do you plan on growing your business or entrepreneurial mindset?
7. What was the toughest moment in your business journey? How did you overcome it?
8. 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.