Best Career Advice Questions to Ask a Mentor

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This post was originally published in September 2023 and has been updated for freshness, accuracy, and comprehensiveness.

Are you about to start your journey as a mentee? Getting guidance and career advice from someone who has transitioned your path and dealt with its ups and downs is the best way to propel and unlock your professional progress. And since you’re meeting for the first time, it’s important to have a clear idea of how to properly prepare your mentoring session and the best questions to ask a mentor. 

What topics can you address during your mentorship?

Mentoring sessions allow you to cover different topics that allow you to develop many aspects of your personal and professional development. The idea is that according to your current needs, concerns, and goals, you should pick the topics you’d like to address during your time with your mentor. 

Here are a few topics you can reflect on to prepare for your next mentoring session:

• Employee development
• Relationship building 
• Problem-solving
• Leadership in the workplace
• Productivity hacks
• Workplace culture

Be sure to explore these topics and select those that are more aligned with your current career path and objectives before reaching out to a potential mentor or planning your next mentoring session, in case you’re already in a mentor-mentee relationship. 

Tips for preparing your mentoring session

Before diving into some career advice questions to ask a mentor, make sure you have everything ready for the meeting. It goes beyond knowing what things to ask a mentor. It’s about setting the ground and doing all the prep to get the most out of your mentor-mentee relationship. Get a head start for your interview by following these tips.

Establish your mentoring session goals

Setting goals is key when it comes to finding the best question to ask your mentor and getting the most out of your meeting with them. Start by establishing the goals for each mentoring session, then set the objective for your whole development process; that way, you’ll tailor your career path questions and share your growth plan with your mentor more easily. 

Define your development objectives by prioritizing SMART goals (specific, measurable, achievable, relevant, and time-bound). This will allow you to focus your efforts on each of these career advice sessions and ease your mentor’s job in tracking and assessing your progress.

Identify your concerns

Getting the most out of your mentoring session implies evaluating and defining in advance the topics you’d like to discuss for each session. Your mentorship questions should focus on your overall career development and its stages, as well as the objectives, results, or skills you’ll address each session. 

If you’re following up on any progress, assignments, or lessons from previous mentoring sessions, then make sure to cover any doubts or next steps in your list of questions to ask your mentor. Other career advice topics and questions you could tackle during your mentorships are self-improvement and building skills, situational, business, and leadership advice, or just storytelling about your and your mentor’s experiences. 

Hold yourself accountable

Mentoring sessions are about productivity and growth. The questions you must ask your mentor won’t be the only thing to discuss. You should also be prepared for the topics they have in mind to check on your progress; in fact, they’ll have questions to discover your objectives and challenges, as well as find out what’s the best way to use their skills and experience to help you. 

Among the topics your mentor will likely address, there will certainly be room for questions to circle back to on your progress and evaluate how you follow their advice. This means you must make yourself accountable before, during, and after your mentoring sessions. Have a clear overview of any advice you’d like to know to improve your method or overcome a challenge.

Be clear and specific

Your first career advice sessions will be less fluent because you and your mentor will have just met each other. Nevertheless, you should always keep the conversations straightforward and clear. Of course, small talk every now and then works to improve the rapport, but don’t force conversations. 

Remember your mentor is taking time out of their day to meet with you, so be respectful and thorough with their time. Make sure to prepare your mentorship questions for each session in advance and have all your assignments ready. 

Set the pillars and questions for your meeting

As mentioned above, listing your concerns is vital when crafting your questions to ask a mentor. Once you’ve established your topics of interest, you should write your questions and organize them by pillars. Aside from clearing your doubts, classifying your mentorship questions will boost the conversion, making it more fluent. 

If you’re still figuring out how to categorize your mentor interview questions, here are a few mentoring session topics you can use to get a head start:

• Professional experience
• Career development
• Leadership
• Company life
• Work-life balance

50 questions to ask your mentor

If you’re still tailoring your list of questions to ask a mentor, check out this boilerplate selection. Remember to adapt them to your needs, keep them specific and straightforward, as well as contextualize them to allow your mentor to understand your case and provide more meaningful answers. 

Here are gpac’s 30 best questions to ask your mentor, classified by categories for getting the most out of your mentee experience. 

Questions to ask a mentor about their professional experience

Your mentor’s career experiences are one of the first topics you could talk about with your mentor, not only to start building a meaningful relationship but also to know more about the aspects of their journey that will help you the most. Here are some sample questions you can ask your mentor about their professional experience:

• Where should I lean into my strengths?  
• How am I certain I’m in the right career? 
• What are the main challenges you’ve faced in your position?
• What skills boosted your professional development?
• Which professional accomplishment are you most proud of? 
• Which chapter of your career is the one you’ve enjoyed the most? 
• How do you combine your passions with your work? 

Questions to ask a mentor about career development

Once you’ve learned more about your mentor’s background, you can mirror their experience over the years with your goals and path so you can craft a plan to develop new skills or plan the next step in your career. Here are a few questions you can ask your mentor, who will give you feedback to plan your professional development:

• Should I consider a career change?
• How did you stay competitive over the years? 
• How should I discuss a potential promotion with my manager? 
• Where do you turn to when you seek continuous learning? 
• What habits have made you more productive? 
• What’s the best advice you have to help plan a career? 
• How far ahead should I plan my career goals? 

Questions to ask a mentor about leadership

If you’re interested in transitioning into a management role, you should get the most out of your mentor’s leadership experience. Even if you haven’t considered this aspect of your career development, covering this topic with your mentor will help you weigh in if you have the makings for a leadership position. Here are a few questions you can ask your mentor to explore your leadership skills:

• How would you define your leadership style?
• How do you keep effective communication? 
• What skills are a must for a lead? 
• What do you do with the negative feedback you receive from your team?  
• How can I lead without being a manager? 
• What would you say are the main responsibilities of a leader? 
• How do you keep your feelings separate from your decision-making?
• How can a leader be transparent without oversharing? 
• How can I set myself to become a leader early in my career? 

Questions to ask a mentor about company life

Navigating daily or complex situations at work is a commonly underestimated challenge that requires a combination of strategic thinking, communication proficiency, and emotional intelligence. Your mentor’s corporate journey can give you insight into any situation you may encounter at the office, so make sure to ask some of the following questions about company life:

• Who are the people I need to align with in my company to achieve success?
• What’s the best way to persuade colleagues? 
• What should I know about a company’s structure or culture to advance in my career?
• What company resources should I take advantage of? 
• What’s the best way to show support to my team and company? 
• How can I match my personality to my company culture? 
• How can I deal with a stressful work environment? 

Questions to ask a mentor about skill-building

If you’re looking to excel in your role, get a promotion, or make a career change, you’ll need to reshape or upgrade your skill set. Whether enhancing your skills is part of a step-by-step to achieve your goal or simply wanting to be more confident while speaking in public, ask your mentor these questions to know the best way to level up your abilities: 

1. What skills do you recommend me to acquire/develop to move ahead?
2. What skills are better to become a proficient negotiator? 
3. What soft skills have allowed you to advance in your career path? 
4. How can I become a better public speaker? 
5. Which of my current skills will contribute more to my career growth? 
6. Do you identify any skill gaps in my profile/resume? 
7. What skills are currently valued more in our industry?
8. Do you recommend a specific course or certification to excel in my role?

Questions to ask about facing challenges

Whenever an obstacle shows up in your way, it’s important to know how to approach them and come up with a strategy to overcome them. With all their experience, mentors have managed and sorted out challenging situations, so make sure to get the most out of their insight in this matter. Here are some questions you can ask them about the best way to face challenges: 

1. How do you recommend to approach a challenging conversation? 
2. What are your conflict-resolution strategies?
3. How do you deal with mistakes at work? 
4. What’s the best way to manage work-related stress and fatigue?
5. How do you approach disagreements with peers or managers? 
6. What’s the best way to perform a task in which you have little to no experience?
7. Do you identify a weakness that’s stopping me from advancing in my career path?
8. What problem-solving skills are a must in my profile?

Questions to ask a mentor about networking

Building professional relationships has become a game-changing strategy for accessing more job opportunities and ultimately advancing in your career path. Contrary to what it seems to be, relationship-building goes beyond handing business cards or making connections on LinkedIn; it’s about establishing genuine and mutually beneficial relationships with professionals in your field. 

Here are some questions you can ask your mentor to gain insight into networking best practices:

1. Has networking led you to a significant career opportunity or growth? 
2. Do you recommend attending a specific networking event, conference, or association? 
3. How have you nurtured your professional network over time? 
4. What kind of profiles/professionals in my field should I contact? 
5. Can you suggest any specific networking strategies or techniques? 
6. Do you have any tips for networking on specifically LinkedIn? 
7. How do you cultivate relationships with your network contacts? 

Questions about personal growth and well-being

Not all aspects of your interview with your mentor need to be work-related. Personal development is a key aspect of your career growth, and it ultimately sets the foundation for professional success. Your mentor can share valuable insight on how to achieve the right work-life balance, so make sure to ask them some of the following questions about your well-being.  

1. What does your daily routine look like outside of working hours? 
2. What hobbies allow you to be relaxed and inspired for work? 
3. What do you do to keep a healthy work-life balance? 
4. Do you recommend a specific practice or resource to improve my well-being?
5. What do you do to keep work-related stress out of your household?
6. How do you prevent yourself from burnout?
7. What values do you find more important to succeed both personally and professionally?

Now that you have a clearer overview of which topics you should approach in your mentoring session and some questions to ask your mentor, make sure to get the best out of every meeting and apply every career advice you’ll get.

Contributed by Luis Arellano