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Law Technology Today


Easily Manage your Firm’s Mentoring Programs with Mentoring Software

Gil Katz


  • Discover the types of mentoring programs that help associates through every stage of their career. Explore the elements that make a great mentoring program, from registration to matching algorithm options and uses of AI to make the best matches.
  • Managing multiple mentoring programs can be a daunting task. Using mentoring software most tasks can be automated to free your time.
  • Artificial Intelligence (AI) tools are making it possible to find that “needle in the haystack” type of information that mentors and mentees may have in common to help make the best possible matches.
Easily Manage your Firm’s Mentoring Programs with Mentoring Software

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1. Mentoring Programs at Law Firms 

Recently a growing range of law firms have been launching and refining mentoring programs to support associates at every stage of their career. Mentors also learn new perspectives and tech tips from the next generation of lawyers. With AI tools becoming more relevant in legal practice, communication across the generations is now more important than ever.

1.1 Types of Mentoring Programs 

From interns to partners, separate mentoring programs should be designed for every stage in a legal career:

  1. Recruiting - connect summer clerks with associates to acquaint them with the firm, procedures and making friends at the firm.

  2. Entry-level support - connect new associates with experienced attorneys for onboarding and sharing experiences.

  3. Associate growth - match with peers for shared professional development.

  4. Becoming a Partner - match senior associates with partners to complete missing skills needed to become a partner at the firm.

Each program has a different group of participants, mentoring resources and some people may be involved in multiple programs at the same time.

1.2 Registration Options 

There are several ways to bring your people on to the mentoring program:

  • Open registration - with admin approval of accounts.
  • Single Sign-On (SSO) integration - login with their existing accounts.
  • Invite-only - upload a list in the admin panel and only this group could participate.

Each program’s registration form requires unique questions relevant to that stage of their development at the firm. Some considerations include:

  • Location - match with a mentor at the same office (or not - as desired).
  • Practice groups, industries and interests - to find relevant mentors.
  • Preferred mentor - enable the mentee to name their preferred mentor and if available the software could auto-match them.
  • Multiple mentees - enable mentors to select how many mentees they want to help. The software could automatically remove that mentor from the list of potential mentors once their capacity is full.

1.3 The Matching Process & Algorithms 

There are several options for matching:

  • Self-matching - mentee selects a mentor - the mentor approves or declines. 
  • Hybrid matching - self-matchng plus admin approval before matched.
  • Admin matching - review top mentors for each mentee and select matches.
  • Auto-match - let the software make the matches.

Matching algorithms can be customized by the mentoring software provider:

  1. Define which registration questions are the same on both mentor and mentee forms.
  2. Assign a priority per matching question (P1, P2, etc.) and a point system. Questions with multiple checkboxes can have points for the first matching selection, or less points for each checkmark that matches.
  3. Some questions may need to override all others. For example, if pairs must be at the same location, that requirement can override all other selections.

The software compares the mentee with all possible mentors, assigning a “% Match Score” for each potential mentor match. It then displays the potential mentors in the order of their Match Score for easy reviews and selection.

The potential mentors may be displayed in a table, tiles with a pop-up, or a swipe view. The key is to be able to compare the details of the mentee next to the mentor to find out how much they have in common and how well they match.

1.4 Communications

Once matches are made they can send messages and schedule meeting by either:

  • Email suggested time, place or preferred web conferencing tool.
  • Book online calls via integrated third-party tools.
  • Meet in the system via built-in video conferencing tools.

While automating everything sounds great, often there are problems making it work. There are many communication tools these days and people have personal preferences. Often the mentor’s preferred communication method is followed. It may be best to simply email the suggested meeting request and book the call outside of the mentoring software.

1.5 Mentoring Resources

At each stage of development a mentee may need some unique resources, but most mentoring resources are often generic to remind both mentees and mentors what to expect. These may include a First Meeting Checklist, Ice Breaker Questions, Do’s and Don’ts, reminder about the Differences Across the Generations and more.

A library of one-page resources and a video library along with simple training quizzes that simply check that they read or viewed the content can help get everyone up to speed.

1.6 Mentoring Checklist & Activities 

Mentees join the program to get insights from their mentors. The mentoring software can help them “create their own adventure” through a:

  • Mentoring Checklist - how to prepare for the first meeting, set availability, planning.
  • Personal Journal - to take quick notes during or after meetings.
  • Goal Setting - define a few goals to achieve in the program.
  • Tasks & Feedback - turn journal notes into action items towards achieving the goals, while the mentor can provide feedback on them any time.

Automated reminders can be sent to participants to remind them to take notes and the admin panel and reports can easily show how engaged each participant is in the program.

2. Managing the Mentoring Program

The goal of mentoring software is to automate the process as much as possible in order to save administration effort, while tracking activities where possible to provide useful reports. Some key elements and options include:

2.1 Registration & Approvals

Some programs people “Register” for and others they “Apply” for. If applications require eligibility the software can be set so admin must approve new accounts.

2.2 Admin Matching Interface Options 

Often mentoring programs don’t allow mentees to select mentors. Instead, once everyone is in the system the admin makes the matches. This can be done either:

  • Email one by one - review a mentee’s top mentor options, click to match and it’s set to auto-email the pair.
  • Mass email once done - admin match everyone without notifying them, so you could change matches as needed and only once done send a mass email to all pairs, notifying each pair of their match.

2.3 Automate System Emails & Reminders

Admin can prepare system emails and reminders at the start of the program and have them sent automatically as needed throughout the program. This can include emails with links to surveys.

When a new session starts, a system email can be sent to all mentors to RSVP to the new session. With one click they could select to join the new session - saving the administrator a lot of communication efforts.

2.4 Progress Surveys 

Often there are halfway and completion surveys. These could be done with the mentoring software or by integrating a third-party survey tool. The key is to keep all the data in one place so it’s easy to analyze the results.

2.5 Tracking Activity & Reports 

The main Key Performance Indicators (KPIs) for mentoring programs are:

  • Participation - Number of mentors, mentees and matches.
  • Engagement - Level of participation (checklists, journals, tasks and goals achieved).
  • Satisfaction - survey results and testimonials.
  • Performance - long-term results in terms of retention and promotion.

3. Leveraging AI in Mentoring Software

3.1 Find Matching Terms in Text Fields & Resumes/CVs

Matching algorithms usually use questions with drop-down selections and checkmarks assigned to a point system to list potential mentors by their % Match Score.

AI can now also read through open text fields and uploaded resumes and CVs. These tools can read through a huge amount of text, comparing the mentee’s resume for example with hundreds of potential mentor resumes - finding a few matching terms. Then it can display the matching terms in context within the sentences they were found for the mentee or admin to review in the matching process.

For example, the AI tool may find that a potential match both have interest in a niche topic that is not listed as part of any registration question option. The mentee is looking to learn about it and the mentor has experience with it - but without the AI tool there would be no way to find that “needle in the haystack” type of information in the matching process.

3.2 Auto-Generate Suggested Questions & Topics of Discussion

Once the AI tool read through everyone’s open text fields and uploaded resumes and found matching terms - it could also recommend possible topics for discussion. It could formulate these into a list of possible questions for the mentee and mentor to ask each other on their first meeting to get acquainted with each other.

As they say “the AI may know you better than you know yourself”. In this case the AI could be used to help make quick friendships across the firm.

3.3 Long-term Machine Learning (ML) to Suggest Best Matches for Returning Mentors 

Mentoring sessions are often set for 6 months, 12 months or some programs even 3 years, but over time, another AI tool could identify the best mentors and also suggest new mentees based on the mentors past experience with similar mentees. This long-term outlook is also difficult or time consuming for an admin to accomplish without such automated tool.


Law firms provide mentoring programs to support associates throughout their career and mentoring software can help manage these programs.

The level of complexity grows as multiple programs are set to accommodate each stage of attorney development and multiple sessions per year.

By automating the process as much as possible mentoring software can save time, effort and enable managing complex professional development workflows at ease.