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400 Best Leadership Questions To Ask Your Mentor (2023)


Welcome to our blog about mentorship! In the fast-paced professional world we live in, having a mentor can make all the difference when it comes to achieving your career goals. Mentorship is a relationship where a more experienced person guides and supports a less experienced person in their personal and professional growth.


It's a crucial component of professional development that can have a significant impact on a mentee's success. In this blog, we'll dive into the importance of having a mentor, how to prepare for your first meeting, the role of the mentor, and much more. So, if you're looking to take your career to the next level, sit back, relax, and discover the power of mentorship.



What exactly is mentorship?


Mentorship is a professional relationship where an experienced person, referred to as a mentor, provides guidance and support to a less experienced person, known as a mentee, in their personal and professional development.


A mentor shares their expertise and knowledge to help the mentee achieve their career goals. Mentorship is an essential component of professional development, and having a mentor can be incredibly beneficial to the mentee's growth and success.


Why is having a mentor important?


Having a mentor is crucial for professional development because they can provide valuable insights into the industry, offer guidance on career paths, and help the mentee navigate challenging situations. A mentor can also provide support and encouragement, which can boost the mentee's confidence and motivation.


They can act as a sounding board for the mentee's ideas, helping them refine their thoughts and develop their skills. Moreover, mentors can also connect the mentee with a network of professionals who can be valuable resources.


Preparing for your first meeting


Before meeting with a mentor, it's essential to do some preliminary brainstorming. Think about the specific issues or challenges you want to discuss, what you hope to gain from the mentorship relationship, and what you can contribute to the relationship.


Take some time to research your mentor's background, expertise, and career path. This will help you ask more thoughtful questions and make the most of your mentor's time. Consider setting goals for the mentorship relationship, and establish expectations for how often you will meet and communicate.


Being well-prepared for your first meeting can help lay a strong foundation for a successful mentoring relationship.


Finding the Right Mentor


The Role of the Mentor


When it comes to mentorship, the mentor plays a critical role in the mentee's personal and professional growth. A mentor's job is to guide and support their mentee by offering advice, sharing their knowledge and expertise, and providing feedback to help them achieve their goals. Essentially, a mentor is like a compass that helps the mentee navigate the often-challenging terrain of career development.


In addition to providing guidance, a mentor also serves as a sounding board for the mentee's ideas, offering a fresh perspective and helping to refine their thoughts. A mentor can also provide much-needed encouragement and support, helping the mentee build their confidence and motivation to succeed. In many ways, a mentor is like a trusted friend who is invested in the mentee's success and well-being.


Mentorship Programs and Potential Mentors


Finding the right mentor can be a daunting task, but luckily, many organizations offer mentorship programs that can help match mentees with potential mentors. These programs are designed to facilitate the mentoring relationship by providing resources and support to both the mentor and mentee.


When considering potential mentors, it's important to look for individuals who have experience in your field and who have achieved a level of success that you aspire to. Consider reaching out to professional networks or attending industry events to meet potential mentors.


Don't be afraid to approach someone who you admire and respect. Remember, the worst they can say is no, and even if they do, it doesn't mean that you can't learn from their experiences and wisdom.


Qualities of a Good Mentor


A good mentor possesses several key qualities that can make a significant difference in the success of the mentorship relationship. First and foremost, a good mentor should have experience and expertise in the mentee's field. This can help provide valuable insights into the industry and offer guidance on career paths.


In addition, a good mentor should be able to listen actively and provide constructive feedback that helps the mentee grow and develop. They should be willing to share their knowledge and expertise, and they should be able to challenge and motivate the mentee to be their best self. Patience and supportiveness are also essential qualities of a good mentor, as they can help the mentee develop their skills and confidence over time.


When looking for a mentor, it's important to find someone who exhibits these qualities and who you feel comfortable working with. Remember, mentorship is a two-way street, and both parties should be invested in each other's success.


Assessing mentor fit


It's crucial to assess mentor fit to establish a successful mentoring relationship. Ask yourself whether the mentor's experience and expertise align with your career goals. Consider their communication style, availability, and commitment to the mentorship relationship to see if it aligns with your expectations. It's also essential to think about whether you feel comfortable working with the mentor and whether they can provide the support and guidance you need.


Setting expectations for the mentorship relationship


Before starting a mentorship relationship, it's important to set expectations for both parties. This includes setting goals, discussing how often you'll meet and communicate, and defining the scope of the relationship. Establish boundaries, and be clear about what you hope to achieve from the mentorship. It can help ensure that both parties are on the same page and can work together towards achieving your career goals.


First Mentorship Meeting


Preparing for the first meeting


Preparing for the first meeting is a critical step in establishing a successful mentoring relationship. Review your goals and objectives for the mentorship, and consider what specific issues or challenges you'd like to discuss. Research your mentor's background, expertise, and career path, and prepare thoughtful questions to ask. Be open to feedback and guidance, and consider how you can make the most of your mentor's time.


Icebreakers and introductions


Starting the first meeting with icebreakers and introductions can help establish rapport and build a connection between the mentor and the mentee. This can help put both parties at ease and create a comfortable environment for discussion.


Consider asking open-ended questions about the mentor's background, interests, and expertise, and be prepared to share some information about yourself. This can help establish a more relaxed and informal tone for the meeting.


Personalizing the mentoring relationship


To make the most of your mentoring relationship, it's important to personalize it to your needs. Share your career goals and aspirations with your mentor, and discuss how they can help you achieve them. Be open and honest about your strengths and weaknesses, and ask for feedback on how to improve. Remember that the mentorship relationship is a two-way street, and be prepared to offer your mentor something in return, such as your unique skills or insights.


Maintaining the mentorship relationship


To maintain a successful mentorship relationship, it's essential to communicate regularly and keep each other informed about any changes or challenges that may arise. Be respectful of your mentor's time and availability, and be proactive in scheduling meetings and follow-ups. Remember that your mentor is there to support and guide you, but it's up to you to take responsibility for your own growth and development. Stay committed and motivated, and make the most of this valuable opportunity.


Asking Your Mentor the Right Questions


Asking your mentor thoughtful questions is essential for a successful mentorship relationship. Not only does it help to elicit valuable feedback and guidance, but it can also help to deepen your relationship with your mentor. Here are some tips on the types of questions to ask and how to follow up after your meetings.


Tailoring Your Questions


When preparing for a meeting with your mentor, take the time to consider what specific questions you want to ask. It's important to tailor your questions to your unique career goals and situation. Sample questions may include asking about your mentor's career path, their biggest challenge in their current role, or their thoughts on specific leadership skills. The more specific and targeted your questions are, the more valuable feedback you are likely to receive.


Asking Different Types of Questions


It's important to ask different types of questions to ensure a well-rounded discussion with your mentor. Closed-ended questions can help you gather specific information, while open-ended questions can encourage discussion and offer a broader perspective.


Probing questions can help clarify and deepen the conversation, while reflective questions can help you gain a better understanding of your own career goals and priorities. Incorporating a mix of these types of questions can ensure a comprehensive and valuable discussion.


Following Up and Taking Action


After your meeting with your mentor, take time to reflect on the feedback and guidance provided. Consider how you can implement their advice into your own career development. Be sure to thank your mentor for their time and consideration. It's important to establish regular meetings and follow up on action items to ensure that you make the most of the mentorship relationship and continue to grow and develop professionally.


Maximizing Mentor Meetings


Types of Questions to Ask


During mentor meetings, it's important to ask a variety of questions to gain a well-rounded perspective on your career development. You may want to ask about your current role, leadership skills, and career prospects.


It's also helpful to ask for feedback on specific projects or issues and seek advice on how to overcome challenges. Asking a variety of questions can deepen the discussion and provide valuable insights into your career development.


Building a Strong Mentorship Relationship


Building a strong mentorship relationship requires investing time and effort into the relationship. Be proactive in scheduling meetings and be prepared to do the necessary work to achieve your goals.


Take the initiative to ask thoughtful questions and seek out feedback and guidance from your mentor. Remember that the mentorship relationship is a two-way street and that you need to be willing to invest time and effort to make it successful.


Acknowledging Your Mentor's Impact


It's important to acknowledge the impact that your mentor has had on your career growth. Take time to express your gratitude to your mentor and acknowledge the specific ways in which they have helped you achieve your career development goals. This can help deepen your relationship and ensure that your mentor continues to provide valuable guidance and support.


How a mentor can help with specific issues


When facing a particular challenge or issue, a mentor can provide valuable advice and guidance to help you navigate it. To get the most out of your mentor's input, be specific about the problem and ask targeted questions. Be open-minded and willing to consider different perspectives, and show gratitude for their insights.


Gaining a new perspective


One of the greatest benefits of having a mentor is gaining a fresh perspective on your career development. A mentor can provide insights into their own experiences and offer guidance on how to approach various situations. To gain a new perspective from your mentor, be open to feedback, and consider different viewpoints. Ask follow-up questions and clarify points to ensure that you fully understand their perspective.


Exploring innovative ideas for growth


A mentor can offer innovative ideas for personal and professional growth, encouraging you to think creatively and develop new skills. Embrace your mentor's suggestions and be open to taking risks in your career development. Consider ways to integrate their ideas into your professional growth plan and experiment with different approaches.


Respecting your mentor's time and priorities


To make the most of your mentorship relationship, be mindful of your mentor's time and priorities. Consider ways to optimize their time and respect their schedule. Set clear expectations for the mentorship, including how often you will meet and how you will communicate. This can help ensure that you and your mentor are on the same page and can work effectively together towards achieving your career goals.


Developing a Strong Relationship with Your Mentor


Building a relationship of trust and rapport with your mentor


When building a relationship of trust and rapport with your mentor, it's important to approach the relationship with an open mind and a willingness to share personal information.


Consider sharing your career aspirations, your strengths, and your weaknesses. Be receptive to your mentor's feedback and guidance, and be honest about your challenges and setbacks. This will help to create a supportive and trusting environment, which is essential for a successful mentorship experience.


Putting in effort and time into the mentorship experience


To make the most of the mentorship experience, it's important to invest time and effort into the relationship. This means being proactive in setting up meetings with your mentor, being prepared with thoughtful questions, and being open to feedback and suggestions. Remember that the mentorship relationship is a partnership, and you need to be willing to put in the work to achieve your goals.


The value of regular meetings with your mentor


Regular meetings with your mentor are essential for maintaining momentum and making progress towards your career goals. Consider scheduling meetings with your mentor on a regular basis, whether that's monthly or bi-weekly.


This will help you to stay accountable and ensure that you are making progress towards your goals. Use these meetings to discuss your achievements, your challenges, and your plans for the future. Be open to feedback and guidance, and be willing to take action on the advice you receive.


Finding common ground with your mentor


To establish a strong and productive mentorship relationship, it's important to find common ground with your mentor. This could be a shared interest in a particular industry or career path, or a common personality trait or work style. By finding common ground, you can build a deeper level of trust and rapport with your mentor, which can help to make the mentoring relationship more meaningful and effective.


Making the mentorship relationship a priority


To make the mentorship relationship a priority, you need to be willing to prioritize your own professional development. This means being willing to set aside time for meetings with your mentor, and being open to the guidance and feedback you receive. Remember that the mentorship relationship is an investment in your own career development, and that by making it a priority, you are investing in your own future success.


​Frequently Asked Questions


What are the benefits of having a mentor?


Having a mentor can provide a wide range of benefits, including gaining a different perspective on your professional life, developing new skills and competencies, and establishing a strong network of contacts. Mentors can offer valuable insights and advice based on their own experiences, as well as provide guidance and support as you navigate challenges and pursue your career goals.


How do I know if a mentor is a good fit for me?


When considering a potential mentor, it's important to ensure that they are a good fit for your particular situation and goals. Consider their experience, areas of expertise, and communication style, and ask yourself whether you feel comfortable and confident in their ability to provide guidance and support.


You may also want to ask for references or speak with others who have worked with the mentor to gain a better understanding of their approach and effectiveness.


What should I do if I'm not getting what I need from my mentor?


If you're not getting what you need from your mentor, it's important to be honest and open in your communication. Consider discussing your concerns and goals with your mentor and exploring ways to adjust the mentorship relationship to better meet your needs. If necessary, you may also want to consider finding a new mentor who is a better fit for your situation and goals.


How can a mentor help me with my soft skills?


Soft skills, such as communication, leadership, and teamwork, are critical for success in many professional roles. A mentor can provide guidance and support in developing these skills, offering strategies for improvement and feedback on your progress. Be open to feedback and willing to practice and develop your soft skills, and consider seeking out additional resources and training as needed.


What should I do if I'm unsure about what to ask my mentor?


If you're unsure about what to ask your mentor, consider reflecting on your career goals and areas for development, and brainstorming a list of questions that are relevant to your situation. You may also want to seek input from colleagues, friends, or family members to gain different perspectives and insights.


Remember that there are no "right" or "wrong" questions to ask, and that the most important thing is to be open, honest, and proactive in seeking guidance and support from your mentor.


What are some tips for establishing monthly mentoring sessions?


Establishing monthly mentoring sessions can provide a structured and consistent framework for your mentorship relationship. Consider scheduling regular meetings, either in person or virtually, and be sure to set clear expectations for each meeting.


Prioritize your mentorship relationship and be proactive in scheduling meetings and following up on action items. Remember that the bottom line is to make progress towards your career development goals and achieve a common goal with your mentor.


400 Best Leadership Questions To Ask Your Mentor


1. Make your questions specific, not vague


2. “What was your biggest failure and how did you overcome it?”


3. Do you have any recommendations for professional development courses?


4. What’s the best career advice you’ve ever received?


5. Tell me about a recent setback and how you recovered?


6. What can I do daily to improve?


7. When is it time for me to contemplate changing career paths?


8. How do you plan to grow your business or entrepreneurial mindset?


9. Extension questions 💪


10. Do you ever get impostor syndrome? How did you learn to get over it?


11. How do you find meaning and purpose in your career?


12. “How did you become such a good public speaker?”


13. What One Thing Do You Still Struggle With?


14. Is there a strategy to unlearning behaviors that are holding me back in this field?


15. Avoid asking rhetorical questions and keep small talk to a minimum


16. Was there ever a role you applied for and landed, but weren't 100% qualified to do? How did you proceed?


17. “In your career were there any small changes you made to your workplace attitude or approach that had a larger than expected impact on your overall performance or success, and are there any similar changes you think I should consider?”


18. I’m considering a career transition. What would you recommend?


19. How do you resolve conflict as a leader?


20. Tell me about a recent business setback. How did you recover?


21. Are there any leaders that you look up to for inspiration?


22. “Ask your mentor why he or she does what they do. Successful people often have very strong reasons for why they do what they do. If you can identify why you want to do something, the ‘what to do’ and ‘how to get there’ will often come much more naturally.”


23. “What’s the best advice your mentors have given you?”


24. Where do you believe my strengths lie?


25. Which leadership skills were the most difficult to develop?


26. What new skills do I need to move ahead?


27. What’s a good methodology or tool for project management and tracking team commitments?


28. Did you have professional development courses? What do you recommend I should get?


29. What’s a big mistake you’ve made that you’d want others to avoid repeating?


30. Have you ever made a single change that led to tremendous success?


31. “What has been your best and worst job?”


32. “What suggestions do you have for asking for feedback from my peers and bosses?”


33. Where should I be networking?


34. How am I perceived by leadership?


35. Do you feel like you can disclose your whole identity to your colleagues?


36. Did you experience some major setbacks in your business/career path? How did you bounce back?


37. If you were me, what’s the single most important question you would ask you?


38. How can I find meaning in my career


39. How can I show you that I’m improving throughout this mentoring relationship?


40. What are some books you can recommend on leadership?


41. How can I stay competitive in my industry?


42. What qualities are lacking among today’s leaders?


43. What qualifications did you need to have to get where you are in your career?


44. How often do you want to meet?


45. “What do you wish you had asked somebody earlier?”


46. How do you practice allyship at your workplace?


47. “You may never know how your career can pivot to a different direction”


48. “A lot of mentors want to know they made a difference. They want to know what you did as a result of the conversation you had with them—even if you didn’t take the mentors’ best advice. They want to know that their time was well-spent and they are making a difference.”


49. “What were your goals at the start of your career?”


50. “What do you wish you’d known 15 years ago?”


51. I have two very different career path options available to me. Can you weigh in to help me make a final decision?


52. How can I improve my time-management skills?


53. What skills do you consider to be my strengths?


54. “Was there a clear turning point in your career? What happened and how did you navigate it?”


55. What are the most important skills you think I need to work on?


56. What do you see as my strengths?


57. What is your biggest fear, and how did you overcome it?


58. Can you tell me about a time when you had a difficult boss? How did you handle the situation?


59. What Can I Do Better?


60. “How can I develop my public speaking skills?


61. “Just ask for help. Ask where you have room for improvement if you don’t already know yourself, and take the response as an opportunity to learn something valuable.”


62. How I am viewed by leadership?


63. How can I best prepare for our meetings?


64. How do you get a better work-life balance?


65. What’s been your proudest moment as a leader?


66. How do I effectively manage and prioritize my time accordingly?


67. “What is your favorite movie?”


68. “What is something you thought was important but has turned out not to be?”


69. What were some of the challenges you faced in your previous positions?


70. “What types of skills should I be aiming to hone in on?”


71. “How have you recovered from failure?”


72. What are the biggest mistakes first-time entrepreneurs make?


73. I want to be given more freedom and independence in my role, how can I ask for this?


74. Has your definition of success changed over the years?


75. Did everyone understand what I presented at the last meeting?


76. What do you enjoy most about entrepreneurship? What is the hardest thing about it?


77. What’s been the most exciting point in your career?


78. How can I reframe my experience


79. How do I find companies with good job benefits?


80. What’s the most important leadership lesson you’ve learned and how has it proven invaluable?


81. How can I improve my confidence in my public speaking skills?


82. Is there any popular entrepreneurial advice that you agree or disagree with?


83. How do you think this industry will change over the next 5–10 years?


84. What are the essential skills that I should develop to grow quickly in my career?


85. What has been the toughest moment in your business journey and how did you overcome it?


86. How can I cultivate confidence in myself in the workplace?


87. How do you measure your success?


88. How do you keep your teams motivated?


89. Questions about working on your growth mindset


90. How am I viewed? In other words, what's my personal brand in our organization?


91. What are some unique questions to ask in an interview


92. Seek engagement opportunities


93. How did you build the skill of always speaking so engagingly in front of others?


94. What’s your preferred method of communication?


95. Did you find it difficult to start in this industry?


96. “Is there any place I’m falling short? What can I do differently?”


97. “If you value the opinion of your mentor, which you should if they’re a true mentor, you should be able to ask “what would you do if you were me?” in a range of scenarios related to work and life. Tell them the thing that is challenging you and then ask how they would approach the situation if they were you.”


98. What’s the best way to go about asking for a raise


99. Are there any networking groups that you think I should join?


100. What decision netted you the most success in your career?


101. What is one lesson you can teach your younger self?


102. Where do you feel I fall short?


103. Do you have any advice on how I can approach asking for a promotion?


104. “What do you think I should focus on for the next 3-5 years to get to the next level in my career?”


105. What’s the greatest obstacle you’ve overcome?


106. Questions to help you learn from your mentor’s career


107. “How did you know it was right for you? Would you choose it again today?”


108. How would you resolve conflicts with colleagues?


109. How can we improve our mentoring connection?


110. How am I perceived by those around me?


111. How do you determine which weaknesses can be overcome?


112. What do you consider to be my blind spots?


113. What skills have been most beneficial for you?


114. How did you learn to embrace risk-taking?


115. Questions about networking


116. At how fast a clip can one reasonably expect to climb the ladder in this field?


117. “What has been your biggest failure to date, and what effect did it have on you, your goals, your vision, and your future decisions?”


118. Can you tell a story of how you recovered from a massive blunder?


119. How can I be more proactive in carving my own career path and future?


120. “What was a trying time for you in your career and how did you overcome it?”


121. Is there any other way you think we could communicate more effectively?


122. Will changing my career hurt my professional reputation?


123. Hold yourself accountable


124. “This can be situated as a short- or long-term question, but it gives you the opportunity to discuss everything from his core beliefs to problems that need solving to what to learn. While your mentor isn’t a fortune teller, this discussion serves as a catalyst for many ways for you to develop.”


125. What do you wish you had known before taking your first management role?


126. “How can I leverage my strengths in my current role or in seeking a new opportunity?”


127. What was the toughest moment in your business journey? How did you overcome it?


128. How do you successfully stay connected to key influencers who do not work in same office or geographical area?


129. How do I professionally respond to a recruiter


130. How should I go about quitting or giving my two weeks notice


131. How do you assess what feedback is legitimate?


132. What do you see as some of my blind spots and how can I improve?


133. Are there any resources you suggest for improving my organisational skills?


134. “Why do we do what we do?”


135. What Are You Trying to Accomplish This Quarter?


136. How can I combine my interests and passions with my work?


137. How big of a risk is too big of a risk?


138. “Why are we doing so many things when ultimately we all are going to die?”


139. Am I communicating enough with you?


140. “What’s one of the most challenging conversations you remember having?”


141. “What is life?”


142. Think back to five years ago. Did you envision this is where you would be?


143. Do you think I'm taking your advice on board?


144. Can I approach you with any questions I have, if so, how should I contact you?


145. “What are you most proud of?”


146. What do people say about me when I’m not in the room?


147. Seek meaningful advice, but connect with small talk


148. What leaders do you look up to for inspiration?


149. How could I communicate my ideas more clearly?


150. How did you settle into this role?


151. “Do you have a goal-setting process you believe in?”


152. How do you begin to brainstorm business ideas


153. What skill area do you think I need to improve upon?


154. Do you believe in the sunk-cost fallacy?


155. “Where do you see my strengths and weaknesses, how can I improve?”


156. When trying to gain buy-in to implement a new program, what tactics have worked for you?


157. What practices can you recommend for dealing with nervousness when speaking to groups?


158. Do I come across as poised and calm?


159. What is the most useful piece of advice you’ve ever received?


160. What are some of the things in your career that you regret not having done earlier?


161. How do I become a better leader?


162. How did you come across your current role?


163. I have been asked to facilitate a team-building activity at a staff retreat. What are some keys to success?


164. What is considered a good salary


165. What traits do I need to exhibit to stay ahead of the curve in this industry?


166. What Would You Do if You Were Me?


167. How do you find a job that fits your interest and passion?


168. Was there a time you messed up and felt like you’d failed? How did you bounce back?


169. “What opportunities will best help in my personal, professional and emotional growth?”


170. I'm considering a career transition. What are some other areas of the business that might be a good fit for me?


171. If you were me, what’s something you’d aim to change immediately?


172. What’s going on in your life outside of work right now?


173. Do you have book recommendations for the challenges I’m facing?


174. How do I know if I’m in a dead-end job


175. “I think most people say, ‘I have no regrets,’ but really, there are things they would certainly do differently if they had a time machine. I like hearing what my mentors wish they did differently and what mistakes held them back so that I can learn from those.”


176. How did you land your current role?


177. “What one decision have you made that has impacted your career the most?”


178. What are some examples of stories you’ve used for answering questions in the STAR method


179. How do you want to communicate?


180. What’s the most unexpected obstacle you’ve had to face?


181. “What has been your biggest challenge? How did you approach it?”


182. I tried to delegate a task last week and it did not go well. Can we work through what to do differently next time?


183. What should I do right now to improve myself and my career prospects?


184. Use questions as a conversation starter


185. “Time is, in a way, the most precious commodity. Understanding how to make the most effective use of time is crucial. Often, the most successful people have figured this out, and it’s worth asking them where they spend their time and how they feel it benefits them.”


186. outlining your overall career goals


187. How can I let my boss know that I don’t need to be micromanaged?


188. What do people say about me once I leave a room?


189. When did you know you’d “made it” and were where you wanted to be?


190. How do I improve my public speaking skills?


191. Learning questions 🧠


192. What do you see as some of my blind spots?


193. then, get specific about what you hope to achieve through your mentoring


194. Can you offer me feedback on my presence in the workplace?


195. Which people do I need to stick around to maximize chances of success in this field?


196. What made you want to become a mentor?


197. set measurable goals for your mentoring relationship


198. Can you recommend a book or resource for dealing with difficult conversations?


199. What’s an obstacle you couldn’t overcome?


200. What do you enjoy the most about entrepreneurship?


201. “What has been your biggest failure / what did you learn from it?”


202. “Mentors usually don’t want to be revered; they want to help. So, pretending you know everything they’re talking about is a big mistake. Often, you genuinely don’t, so don’t be afraid to ask. They’ll respect you more, and, of course, you’ll probably learn something, too.”


203. “Would anyone like to ask the first question?”


204. “How do I cultivate relationships in a sincere, meaningful way?”


205. “What has been your best worst boss?”


206. “What values drive you?”


207. Can you tell me about a time when you had a difficult boss? How did you handle it?


208. What Do You Mean?


209. What are the biggest mistakes first-time entrepreneurs can make?


210. What advice can you offer on how to progress in my career?


211. How can I become more proactive about defining my career path?


212. Hypothetical questions 🧐


213. Questions about productivity


214. How can I handle burnout from work?


215. Do you think I contribute to the team?


216. How can I stay positive in my current position, career, and chosen field?


217. What life skills have been most beneficial in your career?


218. What’s been the biggest leadership risk you’ve taken?


219. How do I handle this situation better?


220. What are some ‘fun facts about me


221. Was there ever a job position that you applied for and got, but you weren’t 100% qualified?


222. What do you think may impact me moving to the next stage in my career journey?


223. What should I be focused on right now to smoothly transition into the next leg of my career?


224. How do you continue to grow and develop as a leader?


225. “This question invites a wealth of short-term and long-term opportunities for you to learn and do a few things. It helps you understand how your mentor tends to problem solve, enables your mentor to see you in a new light as a resource to help, and gives you a chance to deepen your experience in an industry of interest. Consider any questions to ask a mentor about career path a two-way street of opportunity.”


226. What are some of the challenges you’ve ever faced when raising capital for a business?


227. How do you think others perceive me?


228. How do you brainstorm and finalize business ideas?


229. Questions about improving your soft skills


230. “What do you think have been my core strengths as you have watched me grow over the years professionally?”


231. Ask clear, specific questions instead of vague ones


232. What platforms should I be job searching on?


233. How can I prepare better for my upcoming performance review?


234. “Peak Performance coach Tony Robbins once told me that the difference between success and failure is much smaller than most people think. The key is to uncover the subtle distinctions that separate those who have from those who don’t. So, I’d ask the question, ‘What’s one question you wish you asked someone but didn’t?’ This may help expose what your mentor felt was most important to him or her.”


235. Where do you find your inspiration?


236. What skills do you think I need to get the promotion I’m after?


237. “Time management is an oxymoron. Time is beyond our control, and the clock keeps ticking regardless of how we lead our lives. Priority management is the answer to maximizing the time we have.” - John C Maxwell, best-selling author, speaker, & consultant on Leadership.


238. What’s One Thing You Would’ve Done Differently?


239. How can I respond to a job rejection


240. “What was the process you used to find your ‘why’?”


241. How do I talk about a career change in my resume and cover letter?


242. How do you integrate feedback into your work and lifestyle?


243. How has your definition of success changed over the years?


244. Do you have any networking advice?


245. Did you have a hard time starting out in this industry?


246. Do you think I am on the right track and making progress?


247. Where do you see my strengths and what should I focus on to improve?


248. Where do you see my strengths?


249. How Would You Like Me to Follow Up?


250. What are your goals for this relationship?


251. “Do you recommend graduate school?”


252. How can I develop the right amount of discipline to achieve my goals in this industry?


253. What are your current goals as a leader?


254. “Everyone makes mistakes. The mentor who willingly owns up to these mistakes and helps you to avoid making the same ones is a valuable resource and ally. The openness to share mistakes is a good sign that your mentor is candid, will look out for your best interests, and is invested in your future success.”


255. What are your strong and weak traits?


256. “If you wanted to find the second best answer to a question or problem, what technique would you use?”


257. “What was your path?”


258. “What is your biggest source of pride and joy?”


259. How can I make my coworkers feel psychologically safe


260. What items do you think I should bring to my interviews?


261. Am I viewed as high-maintenance when I send my boss weekly status updates?


262. How can I become a more assertive negotiator?


263. What is the hardest choice you’ve made in your career?


264. How can I shift my body language to convey confidence?


265. Going back 5 years ago, did you picture you would be where you are now?


266. I’ve heard that taking a stretch assignment could help my career trajectory. What are the pros and cons?


267. How can I be more strategic in pursuing my career goals?


268. Do I come across as strategic or tactical in my day-to-day communication?


269. What’s an essential lesson you learned as a result of failure?


270. What’s a good thing to be afraid of?


271. What values do you find most important in a person? How do you commit to these values?


272. How can I tell I’m not cherry-picking which feedback I accept about myself?


273. “Did you ever land a role that you weren’t fully qualified for? How did you prepare yourself?”


274. “How did you get back up after this major setback? Did you ask for help?”


275. I’m looking to take on more responsibility within the workplace, how should I approach my manager about this?


276. My performance review is coming up. What type of preparation do you most appreciate seeing from your employees?


277. “You are made up of thousands of others. Everyone who has ever done a kind deed for us, or spoken one word of encouragement to us, has entered into the makeup of our character and of our thoughts, as well as our success.”


278. Do you have any quick tips for re-energizing an overworked team?


279. Are there any goals you’re still looking to accomplish within your career?


280. What do you think is popular entrepreneurial advice most people don’t understand?


281. How did you develop the skill of speaking so engagingly in front of groups?


282. “What has been the most valuable lesson you’ve learned?”


283. “Do you have any career regrets?”


284. “Mentorship is so powerful, so this question is difficult to answer succinctly; however, I’d ask a mentor to share “career-defining” experiences they’ve had. Understanding how to better identify those unexpected opportunities that could boost your career trajectory would have a tremendous impact!”


285. “Have you seen other processes of finding your ‘why’ you found interesting?”


286. What areas in my career do you think I need improvements on?


287. “What would you do if you were me?”


288. “You make it look so easy. What aspect of your career was more challenging than most people realize?”


289. Do you have a template that you use for long-range visioning and strategic planning?


290. How can I figure out what my personal brand is?


291. What’s your strategy for overcoming failure?


292. What’s one thing you do regularly that you think makes you better at your job?


293. What do you think are my weaknesses?


294. What advice would you give to newbie entrepreneurs?


295. How would you suggest I progress within my career?


296. How do you approach risk-taking?


297. My salary isn’t in line with what my peers are making. How do I ask for more?


298. What do you want to get out of this mentor relationship?


299. “What is your favorite book?”


300. Which values got you where you are today?


301. How do you know it is time to change careers? What are the first steps you need to take?


302. Is there a topic you’d like to discuss?


303. Asking questions is just the start


304. Will a nonlinear career path damage my professional reputation?


305. How Do You Spend Your Time?


306. “What is one thing you wish you would have done, that you didn’t?”


307. What’s One Question You Wish You Asked Earlier?


308. Who should I connect with to improve my career prospects?


309. Why did you want to become a mentor?


310. What are some of the most challenging choices you made to get where you are in your career?


311. When should I give up on a pursuit?


312. How do I become a better team member?


313. When I presented at the last meeting, how did I do? Did my communication style support the message I intended to deliver?


314. What are the first steps to changing a career?


315. “Has there ever been an instance in your career where you felt like you weren’t successful? How do you rebound from failure?”


316. Challenge questions 🏆


317. What are the things I need to learn and develop to help me advance in my career?


318. “Is there ever a life balance?”


319. Focus on topics that aid in career advancement


320. “What do you see as my areas of improvement?”


321. Where do you think you could’ve done better, had you known what you know now?


322. How can I negotiate my start date


323. check in regularly to ensure you’re on track


324. How can I come more ready for our scheduled meetings?


325. Think back to five years ago. Did you envision your career as it is today?


326. What are the biggest challenges and most important lessons you learned in your career?


327. What skills do I need to move ahead in my career?


328. How can I stay connected to key influencers who do not work in same office or geographical area?


329. How is my industry likely to change in the next five years? In the next ten?


330. “At this stage in your career, how did you learn to lead people? As a leader, how did you recruit, develop and retain your staff?”


331. What’s the worst leadership decision you’ve ever made?


332. How can I succeed in a male-dominated field


333. How do you keep your team motivated?


334. How do I come across?


335. How can I answer questions about my salary expectations


336. How can I find companies that are committed to fostering a welcoming, diverse work environment?


337. My boss said I need to be more strategic. What does that mean?


338. “How do you manage you handle nerves when speaking in public?”


339. Ask questions on these key topics to get the ball rolling


340. I would like to discuss my future goals with you, when can we do this?


341. “At this stage in your career, how did you learn one of the following… to plan more strategically, make better decisions, focus on time management, and build improved relationships with people?”


342. “I tried to execute a task and it didn’t go as planned. Could you perhaps help me identify where I went wrong, and how to avoid the issue in the future?”


343. Which values got you to where you are today?


344. What qualities do you think modern leaders are lacking?


345. How did you learn to embrace failure?


346. “What is your favorite quote?”


347. What do you do on the days you don’t want to work or don’t feel interested in your job?


348. Clarifying questions 🤝


349. being clear about your priorities and what you expect from your mentor, such as specific guidance or feedback


350. How can I prepare for tough interview questions


351. What Factors Do You Consider Most Often When Planning for the Future?


352. What’s the best way to reply to a job offer


353. What are you excited about right now?


354. Can you recommend any books on leadership


355. “What is your take on making a career change?”


356. “The biggest question to ask a career mentor is what they think you should do. Explain what position you are in, and leave out all the fluff about how awesome you are. Make sure they have a true understanding of your business and look them dead in the eyes with open ears. If they think you’re serious and actually looking to act on their advice, they will usually give you the best advice.”


357. What Mistakes Have You Made?


358. How do I ensure I’m prioritizing the right things?


359. “Which are the biggest lessons did you learn from this failure, and how have you implemented these lessons?”


360. How can I become better at managing people who do not report to me?


361. What are you most proud of in your career?


362. What are some mistakes you wish you could have avoided?


363. Could you offer feedback on ways to improve my executive presence?


364. Check-in with yourself


365. I’m considering a career transition. What do you see as the pros and cons?


366. “What is the one mistake, habit, or pattern that you still haven’t overcome after years of business?”


367. Questions about your career development


368. How can I get rid of nerves before an interview?


369. How do I become better at negotiating?


370. How can I stay competitive in my line of work?


371. “OK… would anyone like to ask the second question?”


372. How am I viewed (i.e., what’s my personal brand) in our organization?


373. When I was last presenting, how did I do?


374. Why Do You Do What You Do?


375. Why did you decide to be a mentor?


376. “Too often, people rely on their mentors for specific situations or how to handle a particular issue. Mentors are there to help guide you as a person and help you grow bigger and better than you currently are. Ask the hard questions such as, ‘How can I improve?’ or ‘What do I do now that I can and should do better?’ Use them to guide you all the time—not simply when an issue arises.”


377. Who are the people I need to align with in this organization to achieve success?


378. “What do you do for fun?”


379. What gives your job meaning?


380. What’s the most important leadership lesson you’ve learned and how is it valuable?


381. “What are my strengths? Are there any areas where I’m highly competent?”


382. “Learning never exhausts the mind.”― Leonardo da Vinci


383. What are your interests, hobbies, and/or things you do outside business hours? How did you get interested in those things?


384. Why did you decide to go into this field?


385. Establish your career objectives


386. “If you could do it all over again, would you change anything? If so, why?”


387. How do you achieve a work-life balance


388. What are some of the instances that you would have done differently?


389. Can we role-play asking for a raise and a promotion?


390. Do you find any utility in holding onto regrets?


391. What are some soft skills


392. “How do you approach risks?”


393. How can I still carve out time for self-care during my job search?


394. How could I have communicated my idea more clearly?


395. “What resources do you think I need to achieve those areas of focus?”


396. What should success look like at this stage in my career?


397. Do I exhibit any warning signs that indicate this field won’t be right for me in the long run?


398. How can I refine key skills for my career?


399. Are there any other effective and memorable ways to introduce myself


400. Is there a particularly effective strategy for achieving success in this field?


401. Is there any advice you would give to new entrepreneurs?


402. How can I apply my strengths in my daily work?


403. How do you and your partner or spouse talk about your career?


150 Leadership Questions To Ask Your Senior Leaders


When it comes to leadership, there are a lot of questions that can be asked in order to help improve the effectiveness of a team or organization. By asking the right questions, you can gain valuable insights into your own strengths and weaknesses from your senior leaders.


These questions can also help identify areas where more training or development may be needed. Below are 150 questions I'd recommend you ask your senior leaders to help you get started on the path to better leadership.


1. How often does the whole team get together?


2. How do you promote career development for employees?


3. How do you promote new ideas and innovation?


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