Mentoring is a Tw0-Way Street

Originally published in Virginia Lawyer, Vol. 74 | June 2025

Modern lawyer mentorship is no longer one-directional, it’s a two-way exchange of knowledge and experience.

Mentoring by senior lawyers is more important than ever. Time pressures, billing pressures, and client pressures are squeezing the ability of senior lawyers to mentor more junior ones. While in the past, a new associate might accompany a more seasoned lawyer to a routine client meeting, such experiences are now rare. Clients resist overstaffing, and firms want more billable productivity to justify elevated starting salaries. The opportunity for informal mentoring is shrinking, while the need for it is growing. The difficult transition from law school to law practice requires the new lawyer to pick up skills never addressed in academia, such as weathering office politics, fixing mistakes, and building a client base. Yet these abilities are essential to building a successful legal career, and they are best learned from those who have already navigated this terrain.

While it may seem obvious that a new lawyer can learn from a senior lawyer, senior lawyers may make the mistake of thinking they do not benefit equally from the relationship. Mentoring is not a one-way transfer of knowledge; it is a two-way street where the mentor benefits as much, if not more, from the experience. If senior lawyers are open to learning new, even uncomfortable ideas, they will experience both professional and personal growth by mentoring junior lawyers.

Keeping current with legal developments is crucial for all lawyers. Not only are new cases decided every day, but also technological advances, regulatory changes, and emerging legal practices appear at a slower but relentless pace. Recent law graduates have had the benefit of using some of the latest iterations of legal technology. Providers want to make them discover salespeople for their technologies so they can introduce these techniques to their firms. Thus, these new lawyers become resources for what new technologies can do (although in the process, they may pose challenges to the firm’s traditional ways of working).

Mentoring a new law graduate gives the senior lawyer an advanced introduction to recent technologies, which can both accomplish legal work more efficiently and free up time better used for other productive tasks. Technologically sophisticated new lawyers think about legal work from a different point of view. This opens new possibilities on how to accomplish it. For example, the change from analog case digest legal research to digitally based research changed how the results are produced. It required different skills to narrow the results to find the best authority for an argument. Both methods have distinct advantages. Therefore, senior lawyers can teach what they know, but they can also learn the advantages of the new lawyer’s approach. The final product is inevitably better. The open-minded mentor may see a new way through an old problem.

Mentoring, then, becomes a mutual exchange of knowledge and experience. It offers a dynamic process of sharing different strategies and perspectives. Many senior lawyers are skeptical, if not fearful, of the changes artificial intelligence is bringing to the legal profession. They have heard stories about court filings resulting in sanctions where one party used artificial intelligence to write a brief, but the cited cases turned out to be nonexistent. Lawyers, being naturally resistant to change, retain these stories to resist using artificial intelligence in any form. But if we do not learn how the new generation can use AI to their advantage, we will end up being the losers.

Today, law firms, especially the large ones, are using artificial intelligence to draft templates for emails, memos, and other correspondence. They use it for legal research, reviewing documents, and preparing discovery. While most firms are hesitant to use technologies that draw on external sources (out of concern for client confidentiality), they are finding ways to limit it to their internal databases. For lawyers in smaller firms, the most efficient way to become knowledgeable about what artificial intelligence can and cannot do is to learn about it from associates who used it in law school—a sort of firsthand continuing legal education.

Senior lawyers benefit not just from working with an individual mentee but also by expanding that relationship to create their network of new relationships. Meeting the mentee’s friends through lunches and social engagements introduces the senior lawyer not only to the new ideas and perspectives of the next generation but also to their social and business relationships. It can introduce them to a new group of entrepreneurs creating new businesses who need legal advice.

When most senior lawyers (including me) entered law school, there were few women students. Today, women comprise over 55 percent of law students, and women are rising in influence throughout our profession. Not surprisingly, most new lawyers are more concerned about work-life balance and time for family obligations than we were. When our generation joined the bar, technology did not enable us to work remotely. The current generation expects working remotely to be part of how they will practice law. Keeping up with their friends involves more travel and time away. The new generation expects to work hard, but they also expect to work differently. The salary levels they want demand hard work, but they also want a more flexible schedule to perform this work. Just understanding how they think helps us help them become more effective lawyers, while it makes us better firm leaders of more productive and responsive law firms.

At a time when many senior lawyers are ruminating on their legacy, it is good to remember that life only moves in one direction: forward. Rehashing the glories of the past is not leaving a legacy. The cases are over, the clients may have died, and the precedent may be overruled. What lasts is building the future. Helping the new generation find their place in our profession and advance the cause of justice is as much a legacy as any lawyer can hope for. When we look back on our careers, our deepest satisfaction may well come from how we helped the next generation build theirs.

Senior lawyers benefit not just from working with an individual mentee but also by expanding that relationship to create their network of new relationships.