How to Make the Most of Your Mentoring Relationship

University of Chicago Law School Affinity Mentoring Program

Thank you for participating in the University of Chicago Law Affinity Mentoring Program! Below is information for both mentors and mentees on how to make the most of your mentoring relationship during the academic year. While this program is designed for one academic year, we hope your mentoring relationships continues past mentees' 1L year.

If you have questions about the Affinity Mentoring Program, please contact Anna Jenkins, Assistant Director of Alumni Relations, at

Important Dates to Remember

  • November 14: Affinity Mentoring Program Kick-Off Reception
  • February - April 2024: Affinity Group Dinners and Meet-ups


A mentoring relationship is a two-way street

Mentees should expect their mentors to serve as a teacher, role model, and a connector; be interested in their development; offer honest advice and feedback; be a sounding board.

Mentors should expect their mentees to be prepared for each meeting, to ask for advice and feedback, and to set goals to work towards throughout the year.


Having clear lines of communication is key

Consistent meetings will help to strengthen your relationship and build greater trust. It is important that each mentoring pair establish when, how often, and where you will meet. As much as possible, mentees should initiate communication and reach out as needed.

Tip: Don't leave a meeting with your mentor before getting another meeting scheduled on the calendar!


Be prepared for your conversations

  • Set clear goals and expectations for the relationships at the start.
  • Mentees should drive the conversation - know why you are speaking with your mentor and what you hope to get out of the conversations.
  • Listen respectfully and request (and accept) constructive criticism.
  • Always hear your mentor out, even if  you don't take every piece of advice.
  • Wear business attire when meeting with your mentor.
  • Don't forget to say thank you!

Building the Relationship

This is the start of your professional network

  • Be respectful of your mentor's time and willingness to participate.
  • Be prompt in responding to your mentor.
  • Be honestly about your concerns and questions - remember they have been in your shoes before.
  • Follow through on mentor recommendations. If you are given a suggestion ("Call my friend at X firm"), follow-up promptly and report back. 
  • Remember: This relationship extends beyond your 1L year and law school.

You get out what you put in

As the saying goes, you get out what you put in. As with any relationship, it takes time to develop and maintain it. While your mentor is a busy professional, don't be afraid to use them as a resource throughout the year and beyond. Your mentors are excited to meet and work with you - that's why they signed up!

Initial Meeting

Get to know each other:

  • Introductions
  • Take the time to learn about your mentor's career path
  • Share your goals for what you are hoping to accomplish this year and begin discussing how your mentor can help you achieve them
  • Align expectations for meetings going forward

Future Meetings

Focus on one or two topic areas per session and come to each meeting prepared with questions:

1L Year Topics

(Mentees: Remember to share the academic calendar with your mentor!)

  • Study tips and recommendations
  • Exam tips as end of first quarter approaches
  • Legal writing tips as part of the Bigelow process and end of year appellate Bigelow Assignment
  • Class recommendations based on practice area of interest
  • Interested in getting involved? Discuss options like Moot Court, Journals, and Clinics
  • On-campus interviewing tips
  • Preparing for summer associateships and internships
Career Specific Topics
  • Resume and cover letter review
  • Job search strategies
  • Different career path options
    • Big firm vs. small firm
    • Practice areas (i.e., litigation vs. transactional, government, in-house)
    • Non-traditional pathway - academia or business
  • Judicial clerkship process
  • Professional and personal skills needed to success as a lawyer
  • Mock interviewing

Questions to Ask Your Mentor

It can be challenging to know what to talk about with your mentor. Below are some ideas to get you started:

  • What do you wish you would have known before starting law school?
  • How do you become a [insert practice area] attorney?
  • How do I make myself an attractive candidate for employment by the time I graduate?
  • Can you recommend any professional organizations that might be useful for me to join?
  • What classes should I be taking depending on my area of interest and to be ready for the bar exam?
  • How did you get your first job after law school?
  • What projects/cases are you currently working on?
  • What is a typical work day like for you?
  • How is what I am learning in law school different from what it is like in practice?