Maximizing Mentorship: Essential Questions to Ask Your Mentor

Thaisa Fernandes
PM101
Published in
5 min readNov 1, 2023

Mentorship is an essential component of career development. Having someone who can guide you and provide you with insights based on their experiences can significantly accelerate your progress towards achieving your goals. Mentorship can come from various sources, including colleagues, friends, family members, or professional organizations.

Finding the right mentor can be a challenging process, but once you find one, it’s essential to make the most of the relationship. One of the best ways to do this is by asking the right questions.

In this article, we’ll be discussing some of the most important questions to ask a mentor to get the most out of the relationship. We’ll also provide some tips for becoming a great mentor.

25 Questions to Ask a Mentor

The first set of questions we’ll be discussing comes from an article on The Ladders. Here are 25 questions to ask your mentor:

  • How did you get to where you are now?
  • What do you wish you had known when you were starting out in your career?
  • What are some of the biggest challenges you have faced in your career, and how did you overcome them?
  • How have you navigated difficult work relationships or conflicts?
  • How have you managed to balance work and personal life?
  • What are some of the most important things you have learned throughout your career?
  • How have you kept up with changes in your industry?
  • What are some of the most significant risks you have taken in your career?
  • What do you think are the most important traits for success in your industry?
  • What are some of the most common mistakes you see people making in your industry?
  • How do you stay motivated and focused on your goals?
  • What are some of the biggest lessons you have learned from failure?
  • How do you approach decision-making?
  • What are some of the most important skills you have developed over the years?
  • How do you continue to learn and grow in your career?
  • What do you think are the most important qualities of a good leader?
  • How do you handle difficult conversations or situations at work?
  • How do you build and maintain relationships with colleagues, clients, and other stakeholders?
  • What do you think are some of the most significant changes happening in your industry right now?
  • What advice do you have for someone just starting out in your industry?
  • How do you approach networking and building professional relationships?
  • What do you think are some of the most important trends to watch out for in your industry?
  • How do you manage stress and avoid burnout?
  • How do you balance short-term goals with long-term goals?
  • How do you measure success in your career?

The next set of questions comes from an article on Forbes. Here are 40 questions to ask a mentor:

  • What do you wish you had known when you first started in your field?
  • What are the most important skills and values you believe someone in your field should possess?
  • How do you stay up-to-date with industry developments and trends?
  • What advice do you have for someone who is just starting out in this field?
  • What do you think are the biggest challenges facing this industry currently?
  • Can you recommend any books, articles, or other resources that have been particularly helpful to you in your career?
  • What are some of the most important lessons you have learned throughout your career?
  • How do you balance your work and personal life?
  • What do you consider to be your greatest strengths and weaknesses?
  • What do you believe sets successful people apart from those who are not successful?
  • What motivates you to succeed in your work?
  • What has been your biggest failure, and what did you learn from it?
  • How do you deal with difficult coworkers or clients?
  • What strategies do you use to manage your time effectively?
  • How do you prioritize your tasks and responsibilities?
  • How do you handle stress in the workplace?
  • What role has networking played in your career success?
  • Can you describe a time when you had to make a difficult decision, and how did you approach it?
  • What are some of the most important leadership qualities that someone in your field should possess?
  • How do you approach managing a team or project?
  • How do you motivate and inspire your team?
  • How do you deal with conflict in the workplace?
  • Can you describe a time when you had to take a calculated risk, and how did it turn out?
  • How do you stay organized and on top of deadlines?
  • What are some of the most important lessons you have learned about communication?
  • What advice do you have for someone who wants to improve their public speaking skills?
  • What is your approach to problem-solving?
  • How do you maintain a positive attitude, even during difficult times?
  • Can you describe a time when you had to adapt to a new situation, and how did you approach it?
  • What do you think is the most important thing to remember when working on a team?
  • What advice do you have for someone who wants to build strong relationships with coworkers or clients?
  • How do you approach negotiation and conflict resolution?
  • What are some of the most important lessons you have learned about entrepreneurship?
  • How do you approach risk-taking and decision-making as an entrepreneur?
  • What advice do you have for someone who is just starting their own business?
  • What are some of the most important trends or developments you see in your industry in the next 5–10 years?
  • How do you approach work-life balance as an entrepreneur?
  • Can you describe a time when you had to pivot your business strategy, and how did you approach it?
  • What are some of the most important qualities you look for in a business partner?
  • How do you stay focused and motivated as an entrepreneur, even during difficult times?

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Thaisa Fernandes
PM101
Editor for

Program Management & Product Management | Podcast Host | Co-Author | PSPO, PMP, PSM Certified 🌈🌱