Smart Questions to Ask a Business Mentor and Get the Most of It

Smart Questions to Ask a Business Mentor and Get the Most of It

Home » Blog » Smart Questions to Ask a Business Mentor and Get the Most of It

Having a solid mentorship relationship is a great resource for career advice. If you need help to boost your profession, you probably need a good mentor. Throughout your journey, you must identify your strongest and weakest points and develop a plan accordingly.

If you already have your mentor and want to make the most out of your relationship, in this article you will find some useful tips. Check out these questions to ask a business mentor. The following conversation topics and ideas will help you get started.

Establish your Expectations

Those who want to achieve success in their business journey need innovative ideas. Trust is also key when it comes to forming an entrepreneurial mindset. This means that you need to trust your mentor.

Mentorship programs are meant to inspire you and boost your career growth. But many people don’t realize this must be set up from the very beginning.

Here are some specific questions to ask a mentor during the first meeting:

  • Why did you decide to make a career path in mentoring?
  • What goals did you establish for this particular mentoring relationship?
  • I would like to know what you think of my own career goals. Do you mind if we go through them together?
  • How often do you think we should meet?
  • What is your preferred method when it comes to communication?
  • How should I prepare for the next meeting?

Find Out Everything You Can About your Mentor

Feel free to ask your mentor questions about himself/herself. This is a great way for you to find inspiration. For instance, you can ask them about their professional experiences. Questions like “How did you reach this point in your career path?” are also a good choice.

Here are some ideas that may help you learn everything you need to know from a mentor:

  • What was your biggest leadership risk and how did you embrace it?
  • Do you ever get impostor syndrome and how do you get over it?
  • Was it difficult to start your career in the mentoring industry?
  • Can you tell me about the choices you had to make to get where you are now?
  • Have you ever experienced setbacks in your career path? How did you get back on track?
  • Is there anything that you would have done differently?
  • How did you see your career prospects five years ago?
  • Did you ever get a job for which you weren’t 100% qualified?
  • If you go back to your starting point, is there anything that you would have wanted to know?

About Success: Questions to Ask a Mentor

Always keep in mind that your mentoring relationship is a great source to get advice. At some point, everyone has to face challenges and resolve conflicts. If you ask a mentor how he/she has done it, the answers can be quite helpful. Here are some examples:

  • What decisions were key for you to achieve success?
  • What strategies do you find to be most effective?
  • How do you identify those people whose partnership will bring you success?
  • Can you give me networking advice?
  • Is there one specific decision/change that you’ve made that brought you success?
  • What strategies do you recommend in this regard?
  • What leadership qualities should I develop to stay competitive?
  • What was the toughest moment in your career path?
  • What should success look like for me right now?
  • How do you identify success in your experience?

Ask your Mentor about Self -awareness

Self-awareness is one of the best gifts that we can give ourselves. We’re talking about the ability to see yourself as other people perceive you. This provides you with  great feedback,  helping you strengthen your positive perceptions. Here are some great questions to ask a mentor:

  • What is my personal brand in our organization?
  • Which do you think are my strongest character features?
  • What do you consider are my weak points and how can I improve them?
  • What do you think of my leadership skills?
  • What do others say about me when I leave the room?
  • How do you think I can improve my presence and leadership skills?
  • How is my daily communication? Am I perceived as tactical or strategic?
  • Am I perceived as high-maintenance?
  • How can I improve my communication skills to convey my idea more clearly?

Questions to Ask a Business Mentor: How to Improve

When looking for the best career advice you’ll want to know about your skills. Project management, decision-making, and public speaking are only some of the skills that you may need to develop.

If you need help in a particular area, your mentoring relationship can be a great resource to find solutions. Ask a mentor the following questions to get the best answers:

  • What skills should I develop to boost my career?
  • Which areas, do you think, need improvement?
  • What could I have done in a specific situation to improve the result?
  • Can you recommend good professional development courses?
  • What books can you suggest for this specific skill?
  • What skills would help me stay competitive in my area?
  • What is the best use that I can make of my strongest skills?
  • What connections would help me advance in my career paths?
  • What skills would prepare me for the changes in the industry within the next 10 years?
  • What do you recommend for better time management and effective prioritizing?

What Questions to Ask a Mentor When Changing One’s Career

  • What steps should I take if I want a career change?
  • How can I combine my passion with my work if I find my job boring?
  • Can you recommend some tips to define my career path?
  • What is the best way to find meaning in my work?
  • How can a nonlinear career path affect my reputation?
  • How do I address career changes in my resume or job interview?
  • How should I manage when quitting a job?

The Best Questions to Ask a Mentor When You Need Entrepreneurial Advice

First-time entrepreneurs probably need help. Developing an entrepreneurial mindset is not easy. However, if you ask a mentor you can find solutions more easily. Also, a business owner can provide advice in this regard.

They can help you overcome obstacles and find the inspiration that you need. Here are some examples:

  • What is the best and worst part of being an entrepreneur?
  • What are the biggest mistakes one can make and how to avoid them?
  • What advice would you provide to first-time entrepreneurs?
  • What is the best way to brainstorm and reach business deadlines?
  • How to solve problems effectively?
  • What is the best approach when it comes to developing your business?
  • Can you tell me about the toughest moment in your career path? How did you solve it?
  • Is there any popular entrepreneurial advice that you disagree with? Which one and why?
  • How would you define the concept of “entrepreneurial mindset”?
  • Do you enjoy owning and running a business? What is the best part?
  • Have you ever faced rejection of your ideas? How did you handle it?


Your mentorship success story starts with a scheduling app to streamline your calendar

Staying organized has never been easier.

You can now manage your business and grow your brand with a single, powerful software that keeps all of your appointments in line, your clients organized and your business booming.

Trafft is perfect for business owners who need to streamline their booking experience both for their staff and their clients.


Trafft handles everything for you, even sending automated email or SMS reminders to your clients. No-shows? Not anymore!

The Trafft booking software adapts to different industries for a blissful online booking experience and employee management.

Want to know more? Check out Trafft’s awesome features to see what you are missing.

Learning About Leadership

Mentors have ample professional experience when it comes to leadership. If you need help in that area, you can always ask your mentor. Leadership qualities are key in project management, so ask your mentor the next questions:

  • What are the key aspects of leading a team?
  • Which are the leaders that inspired you?
  • What leadership books can you recommend?
  • What is the best way to motivate people?
  • What leadership qualities do you think modern leaders lack?
  • How do you recruit top talents?
  • How a great leader can further develop his/her skills?
  • What’s the worst leadership decision you’ve ever made?
  • How can a leader resolve conflicts effectively?
  • What is the biggest leadership risk that one can take?
  • Tell me about your proudest moment as a team leader.
  • What are your goals in your current role as a leader?

Questions to Ask a Business Mentor About Professional Experience

  • Why did you decide to start a career in mentoring?
  • How did you get the position that you have today?
  • What are the biggest challenges that you had to face in this position?
  • What are the skills that worked best for you?
  • Do you have any advice regarding networking groups?
  • What networking groups do you recommend in my case?
  • When you were at the stage where I am now, what advice would have helped you?
  • What is your favorite part of being a leader?

Questions to Ask a Business Mentor About Personal Experience

  • Where do you usually find inspiration?
  • What are your values? Have they changed since you started your career?
  • Can you tell me about your biggest fear? Did you overcome it and how?
  • Why did you choose this career?
  • What do you expect from our mentoring relationship?
  • What do you do when you’re not working? What activities do you enjoy the most?
  • What is the strongest feature of your personality?
  • How can I support you during our relationship?
  • How do you balance your working life with your personal interests?

Mentor Questions About Networking

  • What networking advice can you give me?
  • What networking groups do you think I should join?
  • How to respond professionally in a job interview?
  • What connections can be useful to improve my career prospects?
  • What fun facts can I highlight when introducing myself?
  • How can I introduce myself in a way that causes a memorable impression?

How to Ask for Feedback

  • What improvements do you think I can make to reach my goals?
  • Is there something I could have done differently in this specific situation?
  • What do you think my weaknesses are?
  • How can I turn my weaknesses into strengths?
  • How often should I ask for feedback?
  • How can I improve my communication skills?

Final Thoughts on the Right Questions to Ask a Business Mentor

No doubt, you will have many questions to ask a business mentor. Feel free to ask whatever you need to feel comfortable. Ask open-ended questions that help you discuss the issues that matter to you.

Remember that you’ll get the best answers when you ask specific questions. Growth, development, career paths, entrepreneurship, and leadership are always good topics.

Keep those in mind, revise this guide and you’ll be ready to nurture your mentoring relationship.

If you enjoyed reading this article about questions to ask a business mentor, you should read these as well:


Share article
Milos Timotic
Milos Timotic

Technical Lead