Fun questions to ask your mentee

Sept. 28, 2021

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

After all, there are so many questions, but not enough time to ask them all during mentoring sessions. Whether they’re on mentoring topicsrelated 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 that 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
• 50 good questions to ask a mentor

4 tips on how to ask the right questions to a mentor

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, you’ve decided to get a mentor, so that you can earn 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 deep answer to be effective.

On the other end, B asks a more specific question on nervousness when speaking in public. The mentor can give more actionable advice on this because it’s more specific.

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 topics to get to know the mentor better and initiate a good conversation:

• Expertise, career development, self-improvement and building skills. You can ask specific advice on how to learn and develop a skill or for actionable tactics to help surmount a certain 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 mentoring relationships. 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 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 to make sure that you’re correctly following your mentor’s advice. Ask questions on how to improve your rapport or if you’ve been making good progress throughout this mentorship.
• Career development and growth. Knowing next steps in your career can help you plan ahead. Talk about your personal growth, as well as 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 to have 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 that 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. Asking questions is just the start

Having great questions to ask a mentor is just the start. 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.

50 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 them 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 make the most of your mentorship experience by asking questions about career development, growth, leadership, career path, entrepreneurship and more!

Expertise, self-improvement and building skills

1. Where do you think my strengths lie in?

2. How can I develop the right amount of 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 than ever today, as more companies are embracing 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 experience, do you think I should move elsewhere?
5. I have an 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 how to improve 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 mentorship?

2. Am I progressing in the right direction?

3. Am I correctly listening to your advice?

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?

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?
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?

Career path

Questions to ask a mentor about career paths may vary according to your needs. For example, if you’re looking 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 path?
4. How can I incorporate meaning into my career?
5. What good habits should help me focus on my career?

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 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 don’t neatly fall into these categories. No problem! Come up with your own questions to ask a career mentor, so that you’re able to 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 path, 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.

Remember that asking the right questions to your prospective mentor 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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