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Maturing Mentor

June 1, 2026

Dear Advy,

I’ve mentored young lawyers for many years, and lately I’ve noticed growing anxiety among them about how technology and automation might reduce opportunities for junior lawyers entering the profession. While I don’t believe these tools will replace lawyers outright, I do think they will change how the next generation practices and may require them to be more adaptable in their careers.

As a mentor who is closer to retirement than the start of my career, I sometimes wonder how best to guide them when the profession is evolving in ways I’m still learning about myself. How can I help my mentees remain optimistic about the future while also preparing them realistically for these changes? And is there value in mentors like me continuing in that role, even if we aren’t the most fluent with emerging technologies?

Sincerely,
Maturing Mentor


Dear Maturing Mentor,

Thank you for asking this important question. In any profession, mentoring is so important not only in passing on knowledge but also in providing support in what can be a very stressful environment. Has machine learning made human learning – and in particular human mentoring – obsolete?

It’s interesting that we recently received a letter addressing mentorship from the mentee’s perspective.  One observation that was clear from that letter is that mentees always have to take what they learn from mentors and adjust it to fit their own circumstances.  Mentorship and advising require both the mentor and the mentee to actively consider how one person’s life experience differs from another’s. Mentorship isn’t a monologue of solutions to life’s problems; it’s about understanding how a person’s life experience is similar yet different from our own.

Of course, as a lawyer who has been around the block a few times, my own bias is probably pretty obvious. I’d like to think a flesh-and-blood human can provide something of use. Just for fun, I thought I’d ask AI itself whether mentors should stop mentoring because of artificial intelligence. The answer Gemini provided was:

“No, mentors should not stop mentoring because of artificial intelligence. Instead, AI should be viewed as a tool to enhance, rather than replace, human mentorship, enabling a shift toward "augmented mentorship" where AI handles logistical, repetitive tasks and humans focus on emotional intelligence and deep guidance. 

AI is reshaping mentorship by providing 24/7 access to information, personalized learning paths, and data-driven insights. However, it lacks the human capacity for empathy, trust-building, and understanding nuance, which are essential for professional growth.”

Aww, Gemini that’s a lovely heartwarming answer. Your vote of confidence is making me all teary-eyed!   Of course, Gemini relied on only two sources, one of which itself looked suspiciously like an AI-generated document while the other was a blog post. At any rate, I take its answer as permission to try giving advice to you anyway. I hope my own hopelessly flawed and biased answer can help you even given my human limitations.

Not to be too much like a lawyer, but a lot depends on what “mentorship” means. Mentorship is distinct from teaching and certainly distinct from transmitting data, even if there can be elements of similarity among the three concepts. The purpose of mentorship is not to solve mentees’ problems for them but to provide a sounding board and perspective. The specific advice you give (assuming you give any) is of secondary importance to the support you can provide.

A review of how mentorship is defined in literature on the topic found three themes among all the definitions used:

  • “Mentoring relationships emphasize helping the individual grow and accomplish goals and include several approaches to doing so.
  • A mentoring experience may provide professional and career development support, role modeling, and psychosocial support; mentoring experiences should include planned activities with a mentor.
  • Mentoring relationships are personal and reciprocal, though online mentorship options are creating opportunities to build virtual mentoring relationships.”

Yes, what you might call substantive, or subject-matter advice can be a part of a mentoring relationship, but it is not a significant element.

To put that another way, your mentees were never really coming to you for technical advice in the first place. Did you learn to do legal research using books? How many times have your mentees come to you asking for the best way to note up cases on an online database? My guess is somewhere between “rarely” and “never”. The support you provide has very little to do with your technical knowledge and more to do with your lived experience. I have no doubt there’s a chatbot out there that will masquerade as an experienced lawyer but even the cleverest computer coding is not going to be able to help a junior lawyer through the experience of being laid off from a job, balancing work versus family demands, or dealing with the fallout of losing at trial. For now, at least, there is nothing an artificial intelligence program can offer to help with those issues.

You mention that you are “still learning” about the ways our profession is changing. Those two words are probably the key to why you can be a great mentor. Mentees don’t expect – or shouldn’t expect – their mentors to know everything. One of the most important attributes of a role model is the humility to know you don’t know everything and have much to learn. Modelling being a lifelong learner probably helps your mentees more than anything else you do.

You ask how you can help mentees be optimistic about the future considering the changes we are experiencing and which they will no doubt continue to experience long after you have left the profession.

Writer James Collins coined a term he called the “Stockdale Paradox”. Admiral Jim Stockdale was a prisoner of war in North Vietnam for eight years and, as the highest-ranking prisoner, was called on to provide leadership to the others held in the camp. He later described to Collins the mindset he needed to survive under those conditions and that he tried to instill in others around him. He told Collins that he himself never doubted he would survive the brutal conditions of life in a prison camp and, worse, the burden of not knowing when they would end.

However, the people he termed the “optimists”, he added, would be crushed by the experience. These optimists “…were the ones who said, ‘We’re going to be out by Christmas.’ And Christmas would come, and Christmas would go. Then they’d say, ‘We’re going to be out by Easter.’ And Easter would come, and Easter would go. And then Thanksgiving, and then it would be Christmas again. And they died of a broken heart.”  The lesson, he said, was

“You must never confuse faith that you will prevail in the end—which you can never afford to lose—with the discipline to confront the most brutal facts of your current reality, whatever they might be.”

You might object that, even on its worst days, working as a lawyer is not like being a guest at the infamous Hanoi Hilton. You’d be right. The Stockdale Paradox is nonetheless a useful framework for retaining hope while facing the reality of artificial intelligence and any other challenge to the profession. You are correct to point out that A.I. and other tools will force all of us to adapt. A hope that is grounded in the reality of those challenges is more resilient in the face of change than simply ignoring that reality. If you can model that hopeful paradox for your mentees, you will do them a great service.

One thing you could do to help model that resilient hopefulness is to talk openly with your mentees about what you yourself do to remain hopeful. Younger lawyers as well as lawyers closer to retirement (and everyone in between) can benefit from the help of professional counsellors and peer supporters that your local lawyer assistance program can provide for free. It is very helpful to younger lawyers to know that

(a) even people who have been doing this for decades sometimes struggle; and

(b) there’s no need to wait for a crisis or to be ashamed of asking for help.

Mentees need to see that their mentors themselves struggle too sometimes yet persevere and thrive. I don’t know if that is something you do already, but those supports are free and incredibly helpful, so they are worth looking into.

I don’t want to forget to add this, but in case no one has said this lately, thank you for helping the people around you!

Be well,
Advy