50 First Mentor Meeting Questions

These first mentor meeting questions are a great way to ensure you find the right match for professional development leadership.

Starting out a new career or a job can be daunting; there are loads of people around you and plenty of differential expectations. 

While you begin your training session, you notice that you have many unanswered questions pertaining to your position. So, you may begin the process to seek a good mentor for support and advice.

It’s important to find the right mentor who will be a good fit for you and your goals. Asking the right questions to the potential mentor is the best way to find out if there will be a successful mentoring relationship.

When you finally reached out to a couple of people and some accepted your invitation, you realized that you’re ready to begin the journey as a mentee.

You just scheduled your initial meeting on the calendar. What are the next steps?

One great way to find a new mentor to help with personal or professional development is to meet with them and ask questions. But hold on, what should you ask your mentor? Well fear not, GenTwenty has got you covered. 

First Mentor Meeting Questions

Before jumping into the questions, there are a few steps you can take to ensure your meeting goes as smoothly as possible.

Preparing For Your First Meeting 

Just like other formal and professional meetings, it’s important to be prepared with a checklist filled with good questions. This list of questions can act as an effective way to guide the meeting. 

On your checklist, you should include goals and outcomes you expect your mentor to fulfill. Within these goals, you should include your own expectations of the mentee to mentor relationship.

For example, ask yourself: what skills do I hope to gain as a mentee? And what do I hope to learn as a mentee? Am I able to accept constructive criticism at times, and put in the hard work to grow?

Next, you should also include your own professional experience before joining the company.

As a result, your mentor can know more about you and suggest tips which are better suited towards your situation. For example, if you recently made a career change, your mentor can help you adjust to a new industry. 

The logistics and scheduling of the meetings are important as well.

Ask your mentor when they’re available on a weekly basis at a set time and see if you have any availability which matches with theirs. However, when doing this, keep in mind of vacation times and busy work periods. 

It’s also a good idea to include “conflict resolution” as part of the checklist. So, when challenges do pop up, you and your mentor can follow a guideline in terms of solving the situation yet keeping a positive and professional relationship. 

Before concluding and finalizing future meetings, craft some materials to give to your mentor at the end of the first meeting.

Include a business card just in case they want to reach out, or give them an outline of the structure for future meetings. In this case, your mentor will know what to expect. 

Email a Meeting Agenda 

The first step after setting up the meeting, create a meeting agenda based on the checklist. This will allow your mentor to prepare some answers on their own behalf.

The meeting agenda should be as brief as possible, but if there are important points which you wish to address, include them as well. 

Some meeting agenda components are: 

  • Introduction/Icebreaker 
  • The mentee’s goals and expectations 
  • Logistics and scheduling of future meetings 
  • Conflict Resolution
  • Conclusion 

However, feel free to amend the meeting agenda to your own choice. For example, if you want to include activities, be sure to add some in. 

Be Aware of Your Professional Etiquette 

Throughout the meeting, it is also important to be aware of your professional etiquette, such as the attitude you are displaying. Be sure to read over emails and rewrite them in order to make a good impression, and evaluate your verbal communication style. 

When setting the meeting with your mentor, ensure that you have ample time to complete your previous task and prepare. 

For example, if you had a meeting which ended at 1:00 pm, perhaps setting a meeting at 1:00 pm isn’t the best solution as you’ll be rushing from one meeting to another. 

As a result, give yourself a 15 to 30 minute leeway for preparation. This will also allow you to arrive at the meeting space earlier, which is a bonus point for professionalism. 

Emphasize The Importance of Open Communication, But Keep Boundaries

Being transparent with your mentor is a definite plus.

When you feel uncomfortable about a concept, be sure to address this with them so they’ll be able to help you.

And if something else in your life is bothering you, be sure to address this with them as well. 

When you feel that your goals aren’t being met, letting your mentor know about their concerns will benefit both of you in the long run.

Your mentor will be able to re-evaluate the current approaches to your goals, and you will also be able to re-evaluate your own mindset as well. 

However, it’s also important throughout this process to keep boundaries. Although a mentor guides you along a career path and a professional journey, they are not your best friend.

They are more of a role model and support for your career success.

So, when talking to your mentor, no matter how chill they seem to be, refrain from any company gossip or drama.

Be professional and courteous, and focus on your goals only. These best practices are in your best interest for your mentorship relationship to be successful.

Build Rapport and Trust

Throughout the first meeting, it is also important to build rapport and trust with your mentor.

You can do this by discussing your personal interests outside of work, and having some small talk for a couple of minutes. 

Although trust takes some time to build, ensure that you are open to communicating challenges you face and incorporating your mentor’s suggestions. 

Questions to Ask your Mentor 

As soon as you finish your checklist, you can prepare to ask your mentor some questions pertaining to their career journey, expectations, and goals. 

Moreover, you can also prepare questions to discuss the logistical aspects.

These include schedules, meetings, availability, and resolving conflicts when they arise.

Here are some questions you can include: 

Professional Experience

Throughout the meeting, you can ask your mentor about their professional experience. After all, you met your mentor in order to learn how to navigate your chosen industry or climb the ladder. Here are some sample questions: 

1. What made you decide to select your current career path? 

2. Have you ever planned to be in your current role? 

3. What are your goals for the future? 

4. What were some achievements or disappointments which you experienced throughout your career? 

5. How do you define success? 

6. How did you get past any hurdles or roadblocks? 

7. What skills and experience allowed you to gain your current position? 

8. What is the most meaningful part of your job? 

9. What leadership skills are the most difficult to develop? 

Personal Interests 

It’s always good to add a human touch in business or corporate-related meetings.

So, feel free to ask your mentor about their own personal interests to see if you share any common ground or differences.

Here are some sample questions: 

10. What do you like to do outside of work? 

11. What are some of your favorite hobbies? 

12. What’s on your bucket list? 

13. How would you describe yourself in 3 words? 

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

15. What would you be doing outside of working hours? 

Career Development 

After all, your goal of finding a mentor may be to climb the ladder. You can ask questions related to your mentor’s experience in order for them to share their own journey with you. 

16. What type of training did you find the most effective in terms of developing technical skills? 

17. How can I discuss a promotion opportunity with my boss? 

18. What leadership skill is the most difficult to develop? 

19. How can I prepare for a leadership position? 

20. Are there any resources for me to improve my time management and organizational skills? 

21. Which soft skills do you think are the most important for career advancement? 


It’s also extremely important to set expectations about boundaries, professionalism, and conduct throughout your first session. So, in this case, you and your mentor are well aware of what to expect throughout subsequent meetings. Here are some examples of what you can ask: 

22. What do you expect of me as a mentee? 

23. What role do you expect to have as a mentor? Do you prefer to act as a sounding board or to offer constructive feedback?

24. What topics of discussion fall outside of the mentor-mentee relationship? 

25. How can this be a beneficial relationship to both parties? 

26. How often should I communicate with you? 

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

28. Can I approach you with questions I have and if so, how should I contact you? 

29. What other expectations do you think we should add to the goal’s list? 

30. What do you expect for our future meetings? 


We all get ourselves in unideal situations at work. If you notice that you are going through some challenging times, be sure to address this with your mentor and see how they have navigated similar situations previously. Here are some samples: 

31. I feel that I’m not using the skills which I have gained previously for my current job. What should I do? 

32. I noticed that there is some tension between my boss and I. How should I approach this situation? 

33. I noticed that I’m in a toxic work environment, but I’m not sure if quitting my job is the best solution at this point. How can I navigate this? 

34. I have some business ideas for the company. Are you willing to give me feedback? 

35. I recently got promoted and am taking over a terrible boss. How would you navigate this situation? 

36. When my coworker left, my boss has been assigning me to more tasks without a pay raise. How should I navigate this? 

37. How can I navigate tight deadlines and multitasking in a workplace? 

38. How can I advocate for better work-life balance for myself and my colleagues? 

39. What do you do if work-life balance seems impossible within an organization? 

40. Are there times you had to sacrifice work-life balance to achieve a career goal? 

Logistical and future meetings 

After asking questions pertaining to the mentor to mentee relationship, now is the time to ask questions in regards to future meetings. This will allow you to plan beforehand for unexpected outcomes. 

41. What is your availability like throughout the week? 

42. How frequently do you want to meet and for how long? 

43. Do you want an agenda sent for the next meeting? 

44. What do you hope to address for the next meeting? 

45. How can we tackle situations, when they arise, for our future meetings? 

46. When should we terminate/close the mentor to mentee relationship? 

47. If I were to ever take meeting minutes notes, would you like a copy? Please note that these notes are confidential as well. 

48. How can we address our goals in future meetings? 

49. How can we ensure that the environment is safe and confidential? 

50. Where else can you meet for future meetings? 

In Summary: First Mentor Meeting Questions 

Throughout your first meeting with your mentor, it’s important to ask specific questions regarding your professional goals and the expectations of the mentor to mentee relationship. However, it’s also a great idea to get to know your mentor outside of work as well. 

If you want to add questions in other categories, you can do so as well, as long as they are appropriate for the workplace and your mentor feels comfortable addressing them. 

However, don’t feel pressured to continuously ask questions throughout your first meeting. The initial meeting is usually more informal than the others as you’re learning more about your mentor and they’re learning more about you.

We hope these first mentor meeting questions help make your meeting go smoothly! Check out more of our mentor resources below to help your career development.

More Guide on Mentorship:

About the Author


Candice is currently attending school for social service work. One of her passions is helping others through my writing. In her downtime, you’ll find her listening to music, watching random YouTube videos, and writing about career goals and resumes. She hopes to start freelancing for writing and obtain a leadership position in a public services sector.