Questions to Ask Your Mentor

A mentor can be a key role for your career development.  Always come to your meetings with your mentor prepared for a conversation.  Be open and honest with your mentor, and always be willing to listen and learn.  Make sure your conversations stay fresh by focusing on the four main types of questions:

  • Stories from their career or life 
  • Feedback to increase your self-awareness
  • Advice or guidance about a situation you are going through
  • Advice or guidance about skills you want to build

Introductory Questions

  • Do you have a mentor? What was the best advice they gave you?
  • What is one thing you wish you had known when you were just starting out in your career?
  • How did you get to your current position? Is this where you thought you’d end up?
  • Book recommendations for professional development (or podcasts and other media)
  • Where do you get your news – industry and otherwise?

Resume and Career Goals

  • Would you mind taking a look at my resume?
  • What do you look for in a resume?
  • What are your best interview tips?
  • What skills do I need to be able to advance in my career?
  • What is the best advice you can give to help plan a career long-term?
  • What have been the highlights of your career so far?
  • What would you do differently if given the opportunity?

Developing strengths and overcoming weaknesses

  • How would you recommend I develop my strengths?
  • What are your biggest strengths?  How do you build them?
  • What skills do I need to be able to advance in my career?
  • What are your best tips for overcoming weaknesses? 
  • What is one thing you still struggle with?
  • What was the most difficult challenge you had to overcome?

Core Values

  • What are your personal core values?
  • What do you consider your number one priority?
  • What are you most proud of? What do you consider your greatest achievement?
  • How do you spend your time outside of the office?


  • How do you define leadership?
  • What is the difference between a manager and a leader?
  • Is there someone who you consider a strong leader who may not be in a management position?
  • What qualities does an effective leader have?
  • What makes an exceptional leader?​
  • What is the most important leadership lesson you’ve learned? 
  • How do you decide which risks to take?
  • How do you keep your personal feelings from clouding your decision making? 

Management skills

  • What skills do you think are necessary to be an effective manager? 
  • What do you find is the most effective way to manage people or projects? 
  • What is the most effective way to develop a direct report?
  • How do you decide what to delegate?
  • What do you think is the importance of giving credit to others?
  • Have you encountered challenges when working with or managing different kinds of personalities?

Time management and prioritizing

  • What is your biggest time management tip? Time-saving technique? 
  • How do you decide when to say “no”?
  • How have you developed helpful habits?  Broken time-wasting habits?
  • What are some areas where you want to increase efficiency?
  • How do you balance your work and home life?
  • What do you do to keep learning and growing?


  • What types of communication do you use most often? (Email, phone, face-to-face)
  • What was your worst communication blunder?
  • What is one thing I should never say?
  • How do you weigh or prioritize meeting with colleagues in person versus communicating via phone or email? When are each most valuable?
  • How do you establish lines of communication with colleagues and reports? How do you keep 
  • those lines open?
  • How do you navigate discussions with people who have different communication styles

Relationship building and networking

  • Who has influenced you the most?
  • Is there anyone you’d recommend I meet in or outside the firm?
  • What qualities do you look for in people you spend time with?
  • Do you have any tips for networking/building professional relationships?
  • What challenges have you faced when establishing relationships with colleagues?
  • What is the most difficult challenge of working with a team?
  • How do you work with people who have different personalities?
  • Can you tell me about a time you had a difficult boss? How did you handle it? 

Organizational change

  • How do you encourage innovative ideas from others?
  • What do you do to learn about what an area needs?
  • How do you overcome resistance to change?
  • How do you develop a strategic direction?
  • What are your best tips for establishing yourself in a new area?
  • How do you navigate technical, political, and/or cultural problems?