The Modern Mentor

At its most basic, learning takes two forms – figure it out yourself by trial and error, or find someone who has already made those errors to teach you. Mentorship has been around for as long as humans have seen a need to learn from experience. However, times keep changing. If, as individuals, we want to continue to learn, to progress, and to evolve, at least if we want to do so successfully and efficiently, we also need to change the way that we learn.

The times, they are a-changin’

By now, it’s no secret that the global pandemic of the past few years has accelerated the pace of change in almost every aspect of our lives – forcing us to reconsider our assumptions and adapt to new expectations. While the general idea of mentorship hasn’t changed much over the years, it is important to amend our ways to account for the new times in which we live.

Experience comes in many shapes and sizes. Everyone reading this probably has something to offer to others. Everyone reading this probably has something to learn from others. Every one of us is therefore a potential mentor and a potential mentee. We just have to be willing to share, and willing to learn.

Everything seems connected in our world today. Interest rates affect where someone is going to live, but also whether it makes sense to commute downtown every day to work. Social media engagement is important, not just to stay informed about what your family and friends are up to, but also to attract clients. In order to do our jobs at the highest level, we need to know something about almost everything! Finding the right people to help you navigate through these interesting times is the key to success.

Just put up your hand

I would like to be able to tell you that any success I have experienced in the course of my career was the result of some grand, well thought out plan. Nothing could be further from the truth. I simply had a habit of putting up my hand. Need a junior lawyer on a case? Sure, I’ll do it. Need a volunteer to serve on that Case Management committee over at the Court, or with that brain injury organization? Sure, I’ll do it. I should note that when I volunteered for these roles, I knew nothing about Case Management, or exactly what constituted a brain injury. My plan was not to “fake it until I made it”. My plan was to say “yes” to pretty much everything, and then find smart people who could answer my (many) questions. I figured that if I exposed myself to as many interesting opportunities as possible, the path forward in my career would become clear.

But to succeed, I was going to have to learn from others. I needed to find people who really knew what they were talking about, and ask those individuals to spend a bit more time with me to help me understand. Those leaders, with the knowledge and the willingness to share, made themselves known pretty quickly. And every single one of them was willing to spend time with me, when I asked. Want to be mentored? Just put up your hand and see what happens.

Becoming a mentor

It wasn’t long before people started looking to me for advice and mentorship. Frankly, I didn’t think I had much to offer. I didn’t feel that I had the kind of experience from which others could learn, and I felt like a bit of a fraud. But, I loved to listen, I loved to engage, and I loved being with people (including complete strangers). So, when people wanted to meet with me, I almost always said yes. In the same way that I put my hand up to gain experience, information and insight, I put my hand up in order to offer those things to others.

You have two ears, and one mouth

Talk less. Listen more. That is the key to being a good mentor. That is the key to understanding what a mentee really wants, and needs, from you (which can be two very different things). As a mentor, you want to ask a lot of questions. The best way to start is on comfortable ground – ask about the mentee, about their history, their personal life, their family. Share stories about yourself, both to provide some context for your own learnings, and to get the mentee to open up more about themselves. Listen actively. Focus. Put your phone away, and remove other distractions as much as possible. Demonstrate empathy. The easier you make it for them to talk to you, the easier it will be for them to listen to what you have to say.

Listening can also help you to identify someone in need of mentoring. When appropriate, put your hand up and offer mentorship. I recently had a young man knock on my door during dinner one night, canvassing for a local hospital. I already support that hospital, and I assumed it would be a very short conversation. However, he was clearly very good at his (relatively new, as I later discovered) job, and I let him do his pitch. I asked some questions, and learned more about the specific fundraising drive, but also about how he got the job in the first place. While my family ate dinner, I talked to this young stranger at my front door and learned a little about his history and challenges. At the end of that conversation, I gave him my email and offered to meet with him for lunch one day if he ever wanted to talk. We got together for lunch shortly thereafter.

Share how the sausage is made

A career in law isn’t always pretty. There are a lot of bumps in the road, and a lot of sacrifices to be made, in order to be successful. Most successful entrepreneurs have had some business failure along the way. Most long-standing law firms have gone through difficult times. Most great litigators have suffered big losses. The role of a mentor is not to paint a rosy picture in order to encourage the mentee to stay the course. The role of a mentor is to explain, according to the adage, how the sausage is really made.

We learn far more from our failures than we do from our successes. Therefore, it would follow that those who want to learn from us would be best served by hearing about those cases we lost, the difficult decisions we wish we could make differently, the challenges we had to overcome, the way that we managed our family responsibilities during those difficult times, and more. In my experience, mentees want their mentors to be human, and humans are fallible. Real advice, and real learning, comes from real people. Victories are that much sweeter for the failures that preceded them. Mentees can often relate to the struggle, but very rarely can they relate to the success – at least, not yet. If you really want to help people, help them with brutal honesty, with real stories, with challenges – not to dissuade, but to demonstrate that the bumpy road can be the path to real success, however one measures success. The bumpy road is something that most mentees can relate to.

Everything, everywhere, but not all at once

We are all busy, perhaps more now than ever before. We all have tremendous demands on our precious time. Ideally, mentoring should take place in an environment where people are comfortable, focused, and able to both listen carefully and talk freely, with minimal distractions. Historically, that was associated with meeting for lunch/coffee/drinks. But people aren’t in the office every day. People work more flexible hours. Not everyone drinks alcohol.

So, what is the best environment for modern mentorship? It’s any place that meets the mentee’s and mentor’s needs, on that given day. I have mentored, and been mentored, during breakfast, lunch, dinner, coffee, and over a glass of wine. But, I have also mentored on walks, on bike rides, in the backyard, on a plane, on a park bench, in a car, and pretty much anywhere that two people can have a conversation. If you wait for the perfect lunch date, which has a high risk of being postponed because of some last minute work or other commitment, opportunities for mentorship are easily lost.

Mentorship is a process, not an event. That process can be short, and it can be very long. But there should be no expectation that mentorship is a one-time occasion. Several of my mentorship meetings, in fact, turned out to be one-off conversations. But at the end of each and every conversation, I left it open to the mentee to reach out and have another meeting. Some took me up on that offer. Mentorship is not something that can be rushed. Being a good mentor means understanding that, as long as both participants are willing to continue and feel that the mentor has more to offer, there really is no best before date.

The secret

Why have I agreed to attend countless coffees, lunches, drinks, and all of those more obscurely located mentorship meetings? Because I love it. Because I love people. Because I love learning about people, and listening to their stories, and helping where I am able. But selfishly, I believe that I get way more out of mentoring than I give. I have learned more about life and struggles and overcoming challenges from those I have mentored than they will have collectively learned from me. I have gained way more knowledge than I have imparted. And that’s the funny little secret of mentorship – if you do it well, if you listen and focus, if you share your struggles, if you put yourself out there (wherever “out there” happens to be that day), then both parties tend to gain a tremendous amount.

The world needs more mentors, today more than ever before. I encourage everyone reading this to put their hand up more often – to be willing to learn or experience something new (professionally or personally), and to share the benefit of their experience with others. We all have something to give, and we all have a lot to learn. So, put up your hand and see where it takes you.

Adam Wagman is a Partner and former Managing Partner at Howie, Sacks & Henry LLP. Adam is a past President of the Ontario Trial Lawyers Association (OTLA), and he also served for many years on OTLA’s Board of Directors in addition to holding numerous other leadership positions in the brain injury and legal communities. Adam is certified by the Law Society of Ontario as a Specialist in Civil Litigation and he frequently chairs and speaks at Continuing Legal Education programs. Adam is honoured to be recognized as a leading practitioner in several respected legal directories, and he was named the Best Lawyers 2022 Personal Injury Litigation “Lawyer of the Year” in Toronto. Adam can be reached at 416-361-0988 or

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