150 Questions to Ask Your Mentor For Career Success

Finding and cultivating a relationship with a mentor can help you be more successful with your goals.

In a study of nearly 8,000 people, 91% of workers with a mentor^{1https://www.cnbc.com/2019/07/16/nine-in-10-workers-who-have-a-mentor-say-they-are-happy-in-their-jobs.html} reported being happy in their jobs.

A great mentor is a priceless asset in any career journey.

Take advantage of the knowledge, wisdom, and skills in front of you by asking good questions and following through on the advice you receive.

Pro Tip: If you want a mentor, do you ask them, “Can you be my mentor?” No! This approach is well-meaning but doesn’t work. Here are better ways to find a mentor:

How to Find a Good Mentor (11 Quick Tips)

If you don’t have one yet, you may wonder how to find a good mentor and what to do once you identify someone you’d like to learn from. 

Ask yourself these questions: 

• What are you looking for from a mentor? 
• What are your goals?
• Who do you admire? 
• What do you have to offer? 

Once you identify someone to pursue as a mentor, we recommend reaching out to them for a short virtual meeting—-ask for 30 minutes max.

Tell them what you admire and respect about them and one thing you’d like to learn from them on the call. 

1. Identify Energy Drainers: List tasks that drain your energy to focus on more fulfilling activities. For example, if endless meetings exhaust you, reduce their frequency and duration to free up your time to find a mentor.
2. Align with Your Brand: Are you being authentic? Ensure your activities you engage in contribute to your personal brand or elevator pitch to reinforce your sense of purpose.
3. Take Control of Your Schedule: Make intentional choices with your time to lead a more satisfying and meaningful life. For instance, set aside specific hours for deep work and limit distractions like social media.
4. Incorporate Play: Experiment with new interests and passions through playful activities. Try taking a dance class, painting, or learning a musical instrument to discover what excites you.
5. Develop Communication Skills: Enhance your communication abilities to better express your calling in personal and professional interactions.
6. Commit to a 30-Day Focus: Spend a month focusing on activities that bring impact and joy to discover what truly fulfills you. For example, dedicate 30 days to a new hobby, volunteering, or a personal project to see how it enhances your sense of fulfillment.
7. Follow up your meeting with a thank-you email. Mention some things you discussed in the meeting.
8. Email them once you’ve completed the advice they give you. Did they recommend a book to read or a networking event? Show them you were listening and respect them enough to follow their advice. This also sets you up to ask for another meeting. Acknowledge that you know they are busy, but you’d value having the chance to talk to them about ____.
9. Repeat. Every 3-5 weeks, reach out informally and work on developing the relationship.
10. Pay attention to chemistry. Just because you admire and respect a person doesn’t mean you are a good fit for each other. After a few meetings, you’ll feel good if they are the right mentor for you. 
11. At this stage, bring up the “M” word. Some people recommend a direct ask, while others prefer an indirect approach. Try saying something like, “I appreciate all the time you’ve invested in me lately! I feel like you’re my mentor.” Wait for their reaction. If they respond positively, have a conversation to discuss some of the more formal details. What are your expectations for each other? How often should you meet? Etc.

If they say they don’t have time to be your mentor, be gracious and thank them again for what they’ve already invested in you. But don’t sever the relationship just because they can’t formally mentor you!

Express your desire to stay in contact and occasionally meet when they are available.

150 Amazing Questions to Ask a Mentor

Once you find a good mentor or, preferably, a network of mentors, it’s up to you what you walk away with from the mentor-mentee relationship. Questions can set you up to succeed and help establish a good working relationship with your mentor. 

Questions to Ask at Your First Meeting

At your first formal mentoring meeting, have questions prepared so you can clarify expectations and boundaries for the mentor-mentee relationship. Knowing what to expect is essential for both of you. 

1. How often is it convenient for us to meet? 
2. What expectations do you have for me as a mentee?
3. How can I best be prepared for our meetings? 
4. What’s your preferred method of communication? 
5. How would you describe your mentoring?

Watch our video below to learn how to level-up your life with a professional development plan:

Questions to Ask a Mentor Who Works With You

Some workplaces provide a mentor on the job. Take advantage of that and ask these questions to help you out. 

6. Who do I need to develop relationships with to achieve success?
7. Who will be most important to get buy-in for new projects and ideas?
8. What should I know about our company culture?
9. How can I help improve our company culture?
10. What training opportunities are available to me?
11. What areas would you like to see me improve in?
12. What skills do you feel will be an asset to our company?
13. What are your hopes or expectations for me
14. How does career advancement work in our company? How fast do people usually advance?
15. Does our company offer an annual raise or only give a raise to people who ask?
16. Can you give me feedback on what leadership qualities you’ve seen in me and areas I need to improve?

Find yourself tongue-tied when talking to your manager? Check out our 140 Questions to Ask a Boss. 

Questions to Develop Leadership Skills

Take advantage of your mentor’s hard-earned knowledge about leadership. Remember to be humble and willing to adjust your thinking. 

17. How do you keep a team motivated on a long-running project?
18. How do you help a team develop rapport and trust? 
19. How can I help my team feel valued and appreciated? 
20. Who was your best boss? What made them great? 
21. Have you ever gotten a job you weren’t qualified for? What did you learn from that experience? 
22. What leaders do you admire? What do you admire about them?
23. What do you feel are the most important qualities of a good leader? 
24. What things outside of work are important to make a good leader?
25. What values should a leader have? What values are important to you? 
26. How have you handled major setbacks without growing discouraged? 

Questions to Ask a Career Mentor 

These questions will help jumpstart your career and get you on track to accomplish your career development goals. 

27. What strategies have you found the most successful in this industry? 
28. What qualities do I need to develop to stand out from my peers?
29. Are there any networking groups you think I should join? 
30. What techniques do you use to manage work stress?
31. What is the most important thing you learned from a mentor? 
32. Do you have any daily routines that have been important to your success?
33. Is there something I should be doing at this stage in my career that I haven’t thought of? 
34. What techniques do you use for public speaking? 
35. How can I be more strategic in my work? 
36. Where do you find inspiration? 
37. What books would you recommend I read this year? 
38. Do you have a template you use to set your career goals? 
39. How do you track progress on your goals? 
40. Will you hold me accountable for X goal? 
41. Do you have any suggestions for a professional development course? 
42. I’d like to make a career transition, but I’m still determining what steps I should take before putting in my notice.

Situational Questions to Ask a Business Mentor

Beyond the general questions you’ll ask your mentor, get specific! Talking about success in general terms may feel more comfortable, but letting your mentor into some specifics will help them give you even better advice. 

43. I feel like my current job is stifling my creativity. Do you think there’s something I can do to improve the situation? 
44. My boss always shuts me down in meetings. How should I respond? 
45. I’m in a toxic work environment, but I’m scared of quitting my job. What would you do? 
46. I’m constantly finishing work my coworker should have done. I’m not sure what to do. 
47. I’m interviewing for a new job. Would you roleplay an interview with me? 
48. There’s an opening in a different department that I’d like to put in for, but that department and my current department aren’t on good working terms. I’m worried about how that team will receive me. Do you think changing departments is a good idea or not?  
49. I just got promoted to a position I know my coworker wanted. They report to me now, and I know they resent it. How can I handle this situation?   
50. The leader I’m taking over from was a terrible boss. How can I make a fresh start for the team? 
51. The leader I’m taking over from was a fantastic boss. How can I break through the hostility of the team? I feel like they resent me for not being their old boss. 
52. Everyone thinks the person I’m replacing was amazing, but everything is a wreck. How can I undo the mess they made without seeming like I’m badmouthing the previous worker?  
53. I have some business ideas but need an impartial perspective. Would you be willing to give me feedback? 

Along with questions to ask, there are questions you shouldn’t ask your mentor! Avoid these 5 questions to keep your relationship running strong.

Questions to Ask Your Mentor for Self-Improvement

While you may need help with your negotiation skills, mentoring should also focus on self-improvement. Over time, your mentor will pick up on some of your blind spots. Ask them for their insight by asking these questions. 

54. Have you noticed any recurring conflicts or miscommunications that I have? 
55. What do you feel are some of my biases or preconceptions that are harmful to me and others? 
56. I’m facing ______ (insert stressor or problem at work). What would you do in this situation? 
57. I don’t think I handled X situation very well. What do you think I could have done differently? Do you have any advice on how I can remedy my mistake? 
58. What areas do you feel I need to improve? 
59. How do you balance empathy and compassion while maintaining authority with your team? 
60. I’m not sure I’m valuing the right things. How do you get perspective on what’s important?
61. Am I taking on enough challenges, or do you feel I tend to play it safely?
62. Am I too driven?
63. How do you handle the rejection of your ideas? 
64. How can I ask my manager for more independence at work? 
65. What’s a non-confrontational way to set boundaries at work? 

Questions to Ask Your Mentor for Overcoming Challenges

When you’re up against tough situations, having a mentor can make a huge difference. They can offer practical tips and encouragement. To get the most out of your time with them, try asking these questions to tackle and overcome your challenges.

66. When faced with a setback or failure, how do you maintain resilience and bounce back stronger?
67. I’m encountering resistance from my team when implementing new strategies. How can I effectively manage resistance and garner support for change?
68. Balancing work and personal life seems increasingly difficult. What techniques do you use to maintain harmony and avoid burnout?
69. I’m struggling to adapt to a new role or environment. How can I accelerate the learning curve and thrive in unfamiliar territory?
70. How do you handle conflicts or disagreements within your team or organization while maintaining positive relationships?
71. I feel overwhelmed by the sheer volume of tasks and responsibilities. What methods do you employ to prioritize effectively and stay organized?
72. Facing a tight deadline, I’m finding it challenging to stay focused and productive. What strategies do you recommend for managing time pressure and delivering quality work?
73. I’m hesitant to step out of my comfort zone and take on new challenges. How can I overcome fear of failure and embrace growth opportunities?
74. Dealing with ambiguity and uncertainty is causing stress and indecision. How can I cultivate adaptability and make confident decisions in uncertain situations?
75. I’m encountering resistance or obstacles in achieving my goals. How can I persevere and stay motivated in the face of adversity?

Questions About Entrepreneurship & Remote Work

If your mentor is an entrepreneur or works remotely, ask these questions to prepare you for the unique challenges you’ll face. 

76. How do you have a work-life balance when you work from home?
77. What advice do you give to people wanting to start a new business? 
78. What’s the biggest challenge of being an entrepreneur? 
79. How do you stay connected with the industry while working from home? 
80. What’s something people rarely talk about working from home? 
81. Is there a bad time to start a new business? 
82. What’s something you didn’t realize would be a challenge before you started your business? 
83. What is the most important thing to be successful as an entrepreneur? 

Questions to Improve Soft Skills

According to a survey of over 750 people, 97% of employees said that soft skills impact job performance. Increase your job success by improving your soft skills by asking one or two of these questions in one of your next mentoring conversations. 

84. What have you found to be a leader’s most important soft skill?

85. My team is facing many obstacles, and I’m unsure how to bring them through. How do you lead your team through a difficult situation?

86. I’m struggling with ___ (empathy, confidence, time management, self-motivation, etc.). Do you have any advice on how I can grow in this area?

87. How do you manage many responsibilities without letting things fall through the cracks?

88. How do you build self-awareness?

Questions to Ask a Mentor for Building Confidence

Confidence is key to success in any field. Ask your mentor these questions to build your self-assurance and assertiveness:

89. What steps did you take to build your confidence in your early career?

90. How can I present myself more confidently in meetings and presentations?

91. What techniques do you use to overcome self-doubt?

92. How do you handle criticism without losing confidence?

93. Can you share a time when you felt unsure and how you overcame it successfully?

Scenario-Based Questions on Work Ethics

Don’t just scratch the surface when discussing work ethics with your mentor. Lead them into specific scenarios to gain deeper insights and ask them for practical advice to your situation.

94. I suspect a colleague of mine is cutting corners on projects. How should I address this without causing conflict or damaging relationships?

95. Our team has a tight deadline, and my supervisor is suggesting we exaggerate progress to appease the client. How can I maintain my integrity while navigating this pressure?

96. I’ve noticed discriminatory behavior in the workplace. What steps can I take to address it effectively and ensure a respectful work environment for everyone?

97. My company’s policies seem outdated and unfair. How can I advocate for change without jeopardizing my job security?

98. I’ve been asked to participate in activities that go against my moral values. How can I assert my boundaries without risking my professional reputation?

99. I suspect that my manager is engaging in favoritism when it comes to promotions and opportunities. How can I address this issue without sounding accusatory or creating tension?

100. A coworker constantly takes credit for my ideas. How can I address this behavior diplomatically while still ensuring proper recognition for my contributions?

101. I’m facing pressure from upper management to manipulate data to make our company’s performance look better than it actually is. How can I uphold honesty and transparency in this situation?

102. I’ve witnessed unethical behavior by a senior executive. What are the best channels for reporting such misconduct while minimizing potential backlash?

103. My company’s culture prioritizes profit over ethical considerations. How can I navigate this environment while staying true to my values and principles?

Remember, ethical challenges are opportunities for growth and leadership development.

Questions for Work-Life Balance

Maintaining a healthy work-life balance is crucial for long-term success and well-being. These questions can help you understand how to achieve it:

104. I find myself constantly juggling work and personal commitments. Have you observed any patterns where I could better prioritize my time?

105. Are there any assumptions or beliefs I hold that might be hindering my ability to achieve a healthy work-life balance?

106. Reflecting on a recent work-life conflict, I’m unsure of the best course of action. What alternative approaches would you suggest in handling similar situations?

107. From your perspective, what aspects of my life or work could benefit from improvement to foster a more balanced lifestyle?

108. What hobbies or activities do you engage in to relax and recharge?

109. I often feel torn between competing priorities. How do you cultivate a sense of clarity and perspective on what truly matters?

110. Am I pushing myself enough to grow, or do you sense a tendency to stick within my comfort zone?

111. Is there such a thing as being too ambitious? How do you strike a balance between ambition and maintaining well-being?

112. How can I ensure I’m not overcommitting myself?

Questions to Ask for Improving Communication Skills

Strong communication skills are essential in any profession. If you are struggling on how to communicate effectively, ask your mentor these questions:

113. How can I improve my public speaking skills?

114. What tips do you have for effective written communication?

115. How do you handle difficult conversations?

116. What strategies do you use to ensure clear and concise communication?

117. How can I better understand and communicate with different personality types?

118. How do you maintain professionalism in written and verbal communication?

119. What are your strategies for persuading and influencing others?

120. How do you handle miscommunications or misunderstandings when they arise?

121. What practices do you recommend for improving non-verbal communication?

122. What are your tips for handling public speaking anxiety?

Challenge-Based Questions for Problem-Solving

Empower your problem-solving skills by engaging your mentor in insightful discussions. Here are some questions to help you tackle challenges head-on:

123. Last time we discussed a similar challenge, you suggested I try ____. I’ve attempted it, but I’m still facing some difficulties. Can we explore other options together?

124. In our previous mentoring session, you recommended reaching out to a specific colleague for creative ideas. I haven’t done so yet due to hesitation. Can we discuss strategies for overcoming this reluctance and the potential benefits of seeking their input?

125. I’ve encountered a roadblock in my project. How can I brainstorm alternative approaches or perspectives to overcome it?

126. I’m struggling to prioritize competing demands and tasks. How can I develop a prioritization framework to focus on what truly matters?

127. When faced with uncertainty or ambiguity, how can I gather relevant information and make informed decisions?

128. I’ve identified potential solutions to a problem, but I’m unsure how to evaluate their feasibility and effectiveness. What criteria should I consider in the decision-making process?

129. In our previous conversation, you encouraged me to explore new networking opportunities to expand my professional circle. I haven’t taken any concrete steps yet due to uncertainty. Can we brainstorm actionable ways to initiate and sustain meaningful connections in my industry?

130. You advised me to seek feedback from my peers on my recent project during our last meeting. I’ve gathered some feedback, but I’m unsure how to interpret and act upon it effectively. Can we discuss best practices for soliciting and incorporating feedback into my work?

131. I’m hesitant to take risks or try innovative approaches due to fear of failure. How can I adopt a more resilient mindset and embrace experimentation in problem-solving?

Pro Tip: Take detailed notes during your discussions with your mentor (or at least record your meeting for later watching). Summarize your understanding of the problem and proposed solutions at the end of each meeting right away so you don’t forget.

Don’t have anyone in mind as a mentor? Head on over to our guide: 24 Best Tips for Networking Anytime, Anywhere

Questions to Ask for Time Management

Effective time management can significantly impact your productivity and success. Manage your time effectively with these questions:

132. How do you prioritize your tasks and manage your time effectively?

133. What tools or techniques do you use for time management?

134. How do you stay focused and avoid distractions?

135. Can you share your daily or weekly planning routine?

136. How do you handle competing priorities and deadlines?

137. How do you deal with unexpected tasks or emergencies that disrupt your schedule?

138. Can you share tips for managing time in high-pressure situations?

139. How do you ensure you allocate time for both work and personal activities?

140. What strategies do you use to prevent burnout while managing a busy schedule?

141. What time management advice would you give to someone just starting their career?

Ask These Questions To Hold Yourself Accountable

Take responsibility for your own growth by holding yourself accountable. 

142. Do you feel like I’m teachable? 

143. Are there areas you feel I’m resistant to growth? 

144. How can I be a better mentee?

145. Last time we met, you advised me to _____. I have/haven’t done that…

146. Last time we spoke, you pointed out an area where I can improve. I’m having trouble following through. Can we talk about it some more? 

147. I’ve written my goals and career development plan. Would you mind checking those and giving feedback on them?

148. What habits should I adopt to ensure I’m making consistent progress?

Can you help me identify any blind spots I might have in my self-assessment?

149. How can I better track my progress and measure my achievements?

150. What should I do if I find myself slipping on my commitments?

Pro Tip: Take notes during the meeting to keep track of important thoughts and suggestions, and at the end of the meeting, summarize what you feel they are asking you to do. This will also allow your mentor to clarify if you misunderstood something and gives you the impetus to follow through after the meeting. 

Tips For Asking Better Questions In Any Situation 

Asking questions provides new perspectives and solutions and makes you more likable^{2https://dash.harvard.edu/handle/1/35647952} ! Not sure how to ask questions? Whether you’re talking to your mentor, or anyone else, these tips will help you ask better questions. 

• Watch your tone. When asking a question, make sure you use the question inflection—-a rising tone at the end of the sentence, so that your question doesn’t sound like an accusation. 
• Ask questions that encourage answers. There’s a place for closed questions, but get the conversation started by asking questions that encourage more than a “yes” or “no” answer.
• Ask with humility. Are you asking the question because you want to know the answer or trying to prove a point? If the latter, skip the question altogether. 
• Ask because you care. Ask questions that show you care about the person and what they care about.

Not sure what questions to ask? Get our mega-list of 450 Fun Questions to Ask People in ANY Situation (That Work!)

How to Be a Good Mentee

Nailing the mentee role is all about respect and being open-minded. Your mentor is giving you their time and hard-earned wisdom, so appreciate what they bring to the table and respect them as a person.

If you’re not putting their advice into action, take a moment to reflect on WHY. Own your actions and career choices, be ready to hear the hard truths about your blind spots, and always set aside your ego.

Don’t look for a mentor just to see what you can get, instead:

• Come prepared and eager: Arrive with specific questions, a notebook, and a readiness to learn.
• Show genuine gratitude: Regularly thank your mentor for their time and insights. A heartfelt email or a small gesture of appreciation can go a long way.
• Be a sponge, not a sieve: Absorb all the knowledge and insights they offer. Don’t just let their advice pass through—actively retain and reflect on it.
• Turn advice into action: Implement their suggestions and share the outcomes. If something doesn’t work, discuss it openly and ask for further guidance.
• Own your path: Take charge of your growth. Set personal goals and track your progress, using your mentor’s advice as a valuable resource.
• Seek out the tough love: Don’t shy away from critical feedback. Ask your mentor to point out your blind spots and areas for improvement.
• Build a reciprocal relationship: Offer your help and support when you can. Show that you’re committed to a two-way street of learning and growth.

Remember, being a great mentee not only benefits you but also makes your mentor’s investment worthwhile. Embrace the journey, and you’ll both reap the rewards.

Frequently Asked Questions (FAQs) on Mentor Questions

Final Thoughts on Maximizing Your Mentor Relationship

Finding and cultivating a relationship with a mentor can significantly enhance your personal and professional growth. Here are key takeaways to help you get the most out of your mentorship journey:

• Mentorship boosts job satisfaction. 91% of workers with a mentor are happy in their jobs.
• Know what you want to achieve and admire in a mentor.
• Request a short virtual meeting with a specific learning goal.
• Contact your mentor every 3-5 weeks to maintain the relationship.
• Evaluate the chemistry after a few meetings.
• Discuss expectations and meeting frequency if they are open to it.
• Ask about preferred communication methods and meeting frequency in your first meeting.
• Ask about key relationships and company culture.
• Inquire about team motivation and handling setbacks.
• Follow through on advice, show progress, and be open to feedback.

Engaging with your mentor through thoughtful questions and regular updates can significantly enhance your personal and professional development.

Once you have a mentor, you’ll want to start setting formal career development goals. Get our complete guide on the Professional Development Goals You Must Set Right Now.