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 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. 

How to Find a Good Mentor (5 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. Follow up your meeting with a thank-you email. Mention some things you discussed in the meeting.
  2. 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 ____.
  3. Repeat. Every 3-5 weeks, reach out informally and work on developing the relationship.
  4. 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. 
  5. 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. 

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84 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 style?

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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 navigate your workplace. 

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

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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. 

  1. How do you keep a team motivated on a long-running project?
  2. How do you help a team develop rapport and trust? 
  3. How can I help my team feel valued and appreciated? 
  4. Who was your best boss? What made them great? 
  5. Have you ever gotten a job you weren’t qualified for? What did you learn from that experience? 
  6. What leaders do you admire? What do you admire about them?
  7. What do you feel are the most important qualities of a good leader? 
  8. What things outside of work are important to make a good leader?
  9. What values should a leader have? What values are important to you? 
  10. How have you handled major setbacks without growing discouraged? 

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Questions to Ask a Career Mentor 

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

  1. What strategies have you found the most successful in this industry? 
  2. What qualities do I need to develop to stand out from my peers?
  3. Are there any networking groups you think I should join? 
  4. What techniques do you use to manage work stress?
  5. What is the most important thing you learned from a mentor? 
  6. Do you have any daily routines that have been important to your success?
  7. Is there something I should be doing at this stage in my career that I haven’t thought of? 
  8. What techniques do you use for public speaking? 
  9. How can I be more strategic in my work? 
  10. Where do you find inspiration? 
  11. What books would you recommend I read this year? 
  12. Do you have a template you use to set your career goals? 
  13. How do you track progress on your goals? 
  14. Will you hold me accountable for X goal? 
  15. Do you have any suggestions for a professional development course? 
  16. I’d like to make a career transition, but I’m still determining what steps I should take before putting in my notice. 

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Transform Your Social Skills

  • Boost Your Confidence
  • Enhance Your Relationships
  • Achieve Your Goals

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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. 

  1. I feel like my current job is stifling my creativity. Do you think there’s something I can do to improve the situation? 
  2. My boss always shuts me down in meetings. How should I respond? 
  3. I’m in a toxic work environment, but I’m scared of quitting my job. What would you do? 
  4. I’m constantly finishing work my coworker should have done. I’m not sure what to do. 
  5. I’m interviewing for a new job. Would you roleplay an interview with me? 
  6. 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?  
  7. 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?   
  8. The leader I’m taking over from was a terrible boss. How can I make a fresh start for the team? 
  9. 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. 
  10. 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?  
  11. 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. 

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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. 

  1. Have you noticed any recurring conflicts or miscommunications that I have? 
  2. What do you feel are some of my biases or preconceptions that are harmful to me and others? 
  3. I’m facing ______ (insert stressor or problem at work). What would you do in this situation? 
  4. 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? 
  5. What areas do you feel I need to improve? 
  6. How do you balance empathy and compassion while maintaining authority with your team? 
  7. I’m not sure I’m valuing the right things. How do you get perspective on what’s important?
  8. Am I taking on enough challenges, or do you feel I tend to play to it safely?
  9. Am I too driven?
  10. How do you handle the rejection of your ideas? 
  11. How can I ask my manager for more independence at work? 
  12. What’s a nonconfrontational way to set boundaries at work? 

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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. 

  1. How do you have a work-life balance when you work from home?
  2. What advice do you give to people wanting to start a new business? 
  3. What’s the biggest challenge of being an entrepreneur? 
  4. How do you stay connected with the industry while working from home? 
  5. What’s something people rarely talk about working from home? 
  6. Is there a bad time to start a new business? 
  7. What’s something you didn’t realize would be a challenge before you started your business? 
  8. What is the most important thing to be successful as an entrepreneur? 

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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. 

  1. What have you found to be a leader’s most important soft skill? 
  2. 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? 
  3. I’m struggling with ___ (empathy, confidence, time management, self-motivation, etc.). Do you have any advice on how I can grow in this area?  
  4. How do you manage many responsibilities without letting things fall through the cracks?  
  5. How do you build self-awareness?

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Ask These Questions To Hold Yourself Accountable

Take responsibility for your own growth by holding yourself accountable. 

  1. Do you feel like I’m teachable? 
  2. Are there areas you feel I’m resistant to growth? 
  3. How can I be a better mentee?
  4. Last time we met, you advised me to _____. I have/haven’t done that…
  5. 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? 
  6. I’ve written my goals and career development plan. Would you mind checking those and giving feedback on them? 

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. 

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Tips For Asking Better Questions In Any Situation 

Asking questions provides new perspectives and solutions and makes you more likable! 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!)

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How to Be a Good Mentee

  • Remember, your mentor is investing in you with their time and wisdom
  • Respect what they have to offer but also respect them 
  • Never seek out a mentor for what you can GET from them
  • Be teachable and listen to their advice
  • If you never apply what you learn from them, ask yourself why
  • Take responsibility for your own actions and career choices
  • Expect, and be willing to have your mentor point out your blind spots
  • Set aside your ego

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.

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