Alternative Legal Paths and The Power of Generosity with Tim Wilbur

Welcome to Studying Law Around the World. I'm Claudio Claus. In each episode, I talk with lawyers, law students, and professors from different parts of the world to talk about legal education, careers, and what the profession looks like in real life. We talk about the hard parts, the surprises, and the decisions that shaped their paths. Whether you're planning to study abroad, thinking about working in another legal system, or just curious about how law works around the world, this podcast is for you. Tonight's guest leads the editorial direction of some of Canada's most respected legal publications, including Canadian Lawyer, Lexpert, and others. As global managing editor of Key Media, he's both a trained lawyer and an experienced journalist, which gives him a rare ability to move between legal analysis and storytelling while staying precise and clear. He also hosts the CL Talk podcast, where he speaks with leading lawyers and legal executives across Canada. And I'm glad to have Tim Wilbur joining the conversation tonight. Thank you so much for making the time, Tim. Claudio, it's nice to be here. Amazing. To start off our conversation tonight, I'd love for you to tell us a little bit more about your journey from studying law to becoming the managing editor at Key Media. Sure. So I studied law in the early 2000s, a while ago. And when I was at law school, I did a lot of work on the student paper. So I didn't have a journalism background coming into law school, but I was really interested in media. And therefore, I did, as I said, some work on the student in an eventful time at law school when I was there at University of Toronto. And then I articled at a civil litigation firm in Toronto. And then I didn't get asked back to the firm, so I was looking for work. And my wife convinced me to apply at the Lawyers Weekly. And because I had the student paper experience, and they were looking for someone with a law degree because it was doing editing legal articles written by lawyers. So I started there, and I just fell in love. I was writing stories, being creative, talking to all these senior lawyers, learning about all the big stories that were happening in the legal world at the time. And then a couple of years later, my boss at the time moved. I took over her role, and then I never left. And then I joined my former boss, actually, at Thomson Reuters to become the managing editor of Lexpert. And then I moved to Canadian Lawyer. And then in 2019, we were acquired by Key Media. And I took over the editorial for all of the publications, which, as you mentioned, was Lexpert, Canadian Lawyer, as well as Law Times. Amazing. I'd love to drill down a little bit. You just mentioned a very interesting aspect of getting to hear a lot of stories of big things happening in the profession. What have you learned about the legal profession as a career from sitting on this editorial side rather than in practice? Lawyers. So I kind of joke sometimes that I know a little bit about a lot of areas, but not a lot about any area. So I've spoken with judges, senior politicians, attorney general, leading managing partners at all the major firms, general counsel, lawyers at small firms, criminal lawyers, human rights lawyers, look, all across the gamut. So an impression I have about the legal profession is it's so varied, and there's so many opportunities to move around. You're not stuck roles the way some professions are, where you have to specialize in your officially declared, whatever, certain kind of surgeon or something, if you're a doctor, for example. Whereas with lawyers, they do really move around some, stay in the role that they started maybe at a law firm and become a partner and stay with that. But a lot of lawyers don't. A lot of lawyers move around. They might move in-house if they're at a private practice. They might become a judge. They might go into politics. They might start working at a non-profit, move into business. There are just so many different places that lawyers end up, and their law degree is always, I think, something that is of use to them. So that's the big thing that I really feel about the profession is that there's so many varied things you can do and broad experience you can bring roles, no matter how far along you are. I love that. It has really materialized in your career as well. So I find that fascinating. Also beyond recent media, you also host the CL Talk podcast. I'm curious, drilling down this point you just mentioned about the optionality and what you can do with a law career. How has speaking with these legal leaders across the country shaped what you understand makes a successful career nowadays? I reach a broader audience. Not all the lawyers are comfortable doing podcasts, whereas if you're doing a written article, it's a little bit easier to speak with them. That's an advantage of the podcast. Good journalist is curiosity. So I'm always wanting to learn about new things that lawyers are doing, and I'm always looking out for someone that's doing something interesting that I've never heard of or on the cutting edge of something. They've gone through some really significant achievement, like a big deal they've worked on or a big piece of legislation maybe they've worked on if they're a politician or they've started their own firm. So these are just examples of stories that I've spoken to lawyers about. The lawyers who really are passionate about their clients, and their clients can mean different things. Like if you're a politician, your clients is the public, right? But they're really passionate about who they're serving, not so much the law itself. They may be interested in that, but the ones who are really at the peak of their game, I find just passionate about who they're serving, whether it's their businesses, if they're a corporate lawyer, or refugees and immigrants, if they're an immigration lawyer, lawyers, it's really people who have had difficulties in their life, and they're representing them against this huge state, their rights need to be protected. The passion that whatever area they're in, the sort of bigger picture of what, who they're serving and what they're doing, I think is what drives the really good ones. That's fascinating. That's fascinating. Speaking a little bit about is maybe non-traditional legal paths, paths that are adjacent to law. Spoken with quite a few professionals who are doing working legal marketing and business development who maybe have JD in the background or who did practice for a few years. Are there a few things that you also noticed lawyers did, or that maybe if they're considering these non-traditional legal paths that they should keep in mind if they want to try doing something like that? It depends on the context to what kind of legal, alternative legal career you're seeking. But I think a lot of lawyers who do that realize that traditional practice isn't really suited to them, but you can do it for quite a while is often a great background for building into something else. I think a lot of lawyers who are successful that make it leap into something that they're passionate about is it's not, it's not like you flip a switch and all of a sudden you go to something else. It can be, you can build over time. So for example, if you're a lawyer, as I said, at a private firm, but you do a lot of pro bono work, maybe for an organization that is, you're really passionate about, that can be a way to get a sense, oh, then you're, then maybe you're working with the people at the organization, you're learning what they do. So then you're, you'll start getting a sense of whether it's something you want to do yourself. Another example would be lawyers who go in-house often, not always, but often working on files. Client is, wants them, the external lawyer for that, for a company that they might eventually work in-house at, or not necessarily the client, but in the same industry. So if you're interested in healthcare, for example, you want to work in-house or maybe in a non-legal role in healthcare, if you kind of gravitate to files that allow you to see people and interact with people in that industry, that can be a really good way. So I think if, if you do it organically and kind of seek out things that you think are suited to what you want to do, then often way that naturally lawyers move into something more traditional, more non-traditional, but some lawyers know from the outset, don't want to work at a traditional law firm. They just know immediately that they want to do something different. So I think as long as you, as I said, you have that passion and you want to serve whoever the clients or the, or whoever's benefiting from the place that you're going to, there's a non-profit for example, or moving in government or whatever you have, as long as you have that passion and you, and you have a sense where you're going and you've got some, a network, then your legal degree will never be something you'll, that won't be useful. I've never heard anyone say, Oh, I took this role and I'm really, being a lawyer was kind of irrelevant. Like it really helps in a lot of things. If you're going to music, for example, just being a good business person and negotiating contracts would be something that would be of use as a, as a musician. So that's, I'm thinking of something that's sort of very distant from legal practice. Even then, I think your law degree could be helpful for you, ways that could make you successful in that area too. Amazing. And really enjoyed that one thing you said about talking with lawyers who are doing different things who are doing things don't hear about much or who have big deals, big piece of legislation and so forth. And thinking about that, and I think that very much relates to the work you do. Can you tell us a little bit about trends are shaping the legal profession right now? We hear a lot about AI, we hear a lot about worldly bus, but are there a few things that are very punctual from the legal profession, maybe even specifically in Canada right now? Yeah. I mean, I mean, unfortunately my answer is what you've already talked about is the AI is really is a disruptive force in the legal profession in almost every area that I talk to lawyers on. And I don't think it's hype really feel it is a fundamental shift. So that's one area that is just every lawyer I talked to almost are being affected by it. Also, obvious ones are lawyers at law firms who are doing their work more efficiently, or corporate lawyers, corporate counsel at companies who are able to do a lot of the work internally with these tools and be more efficient, they interact differently with their law firms because of the way these tools are allowing them to analyze information. But there's all sorts of other areas where it's having a profound impact on just recent just today, actually, we published a story where we interviewed or surveyed all of the courts across Canada, about what's the impact what impact AI has had on them really got a lot of information from the courts about this. And this is a really significant thing for them. It's just determining whether they can use these tools and the proper use of them is a big deal. But also litigants are using AI more and more, which is making the court's life quite difficult, actually, because they're getting the volume of pleadings that they're getting, many of which aren't really based on sound legal reasoning. It's having an impact the human elements to that lawyers have when they work with their clients. And often what lawyers do is they help client clients in crisis. So they, that skill is a is a people skill, it's something like AI can't replicate. So it's becoming more and more important, because you're in a big deal, putting together a contract might be able to be automated quite quickly. And so the lawyers aren't spent maybe spending as much time on their own at their computer kind of drafting a contract, because they can do it so much more quickly. But the clients, because they can do it more quickly, they can serve more clients, the good lawyers were doing this already. But the everyone is there's more and more demand is be speaking with your clients, talking them through the issue, coaching them about how to work through their merger, make their argument in court. I think the lawyers who are have that skill are going to become even more than the ones who are the ones who don't didn't focus on that so much are now having to because rote work and the analytical work that they used to do is becoming much more automated. So yeah, unfortunately, AI is the answer. Your question. That's the number one. But there are other things happening in the profession as well, obviously, that are there of interest. But that one is the one that's kind of permeating every area I speak to lawyers on. It's really interesting, because even within this area, there's so many different ramifications where that can go. And I appreciate you bringing some of those up. I know you've been involved in the major legal awards recognition platforms, like Canadian Law Awards, the Lexpert, Rising Stars, others. And I'm curious, after many years now working, seeing this happen over and over again, what are some of the things that separates lawyers who stand out in the profession? You're right. Those are the two big award ceremonies I work on. And the other one that's quite well known, as well as the top 25 most influential, we don't we don't have an event tied to that, like we do with the other two you mentioned. But that one has particular interest with me, because I started at Canadian Lawyer and sort of evolved the awards to be more to bring in an editorial panel of judges. So for all of those awards that you mentioned, Rising Stars, Canadian Law Awards, and Top 25, we have an editorial board panel who ultimately make the final decision. So if someone asked me, how can I win one of these awards? My answer is, well, you got to talk to the judges, because I'm not the one that's deciding it. But I see all the submissions. And one of the things that I find makes lawyers who really serve their clients see their clients' interests, the most important thing, the lawyers, maybe they work on a public policy element of their practice. I spoke last year, I remember, with a lawyer who was a derivatives lawyer, which is not everyone knows what that even is. But why she won the award was more that she sort of identified, I think, this issue that was a broader public policy issue that had to do with, I don't even understand, it was very technical with way, way in currencies, evaluator or something like, like I said, I didn't really understand the technicalities. The point was, she took this issue on, and then pushed really hard to have a whole reform process place for this issue that was really important for her clients, and all of the people that she worked with in this area. So she kind of started this whole committee, and the government eventually brought through all these reforms, due to her, the energy she brought to this issue. Lawyers who sort of see the bigger picture of whatever practice they're in, and really fight for, for their clients in bigger ways than on individual, on the individual level. So that's one thing I really noticed with a lot of the lawyers who win these awards. And the other thing is, a lot of it is going through some really significant and often very difficult process or transaction. So the example with a corporate lawyer, or a corporate counsel would be maybe go through a merger. So their company is acquired or acquire a company with these big corporate deals that can be complicated, and take place over several years. And then even after the deal is closed, there's often a lot of work to do afterwards to make sure that the two entities are actually, the culture is actually properly merged between the two companies. So it can take place over years, and lawyers who are sort of at the center of it, you really feel job is really difficult, and you're going through the most difficult period in your career moment. And that is actually where the top lawyers succeed is by being having grit and pushing through. One anecdote I remember speaking with the general counsel of Rogers, there was a big competition review, and she had to go to court and there was it went through up to the Federal Court of Appeal, it was just several years before the deal could close, it was the most difficult part point in her career. But afterwards, she won several awards, she was a top 25 most influential lawyer, she won one of the Canadian law awards, the deal, the Rogers deal won for that. So I think those two things, the lawyers who are really focused on the bigger picture for their clients, and who maybe have gone through something significant and difficult, and had the grit to kind of make it through and come up with their head held high at the end, even though it was it was a challenging experience. Same with litigators, they might fight a case up through to the Supreme Court or something complicated issues involved, and maybe many other law firms they have to coordinate with just thinking of some of the typical cases that win, that's often wins the awards, and the ones that submissions we get that aren't as good as are sort of more generic, and we'll tell you things like, well, this client, this lawyer is very client focused and top litigator or whatever successful. Fantastic. To wrap up our conversation today, I wanted to hear from you. My audience here are law students, internationally trained lawyers, early career professionals who really are trying to build both a meaningful and lasting career in the field of law. And over the years, I'm sure you've seen many stories over and over again, are there a few pieces of advice that maybe stand out from either people that you interviewed, even from your own experience to those lawyers who want to build both a career that is meaningful, but also that can last long and is sustainable? Yeah, I mean, I think there's one thing that like, I think, puts lawyers kind of getting a lot of lawyers, at least very negative connotations with the idea of networking, connecting with people, a hard thing to do when you're early in your career. But a couple things with that is think of it as something where you're trying to give other people not take initially in your career. So volunteer work, asking when you're meeting lawyers at events or whatever, asking them about themselves, getting them to talk about what why they like their career, sort of don't think of it as something where you're always going to know where the opportunities arise. But if you're if you're in a giving kind of mode where you want to help, then that's just people know that and then ultimately, that's much more effective way to network to kind of go out and find people that you want to help with things, do that for them and don't expect anything in return in the term, because law is a very relationship based profession, but it's also very based on ethics and how you compose yourself. So people see that you're generous and you're interested in them and you're and you want to give, then ultimately, you'll be more successful because they'll want to work with you. And things will things will happen positively in your career that requires patience. Things don't come right away. Often your world is very small in the short when you start out in your career, that might be just one senior lawyer that you're doing all your work for or or just a couple of people around you. But if you're really generous, sort of giving, learn as much as you can from that, then people will notice that. Provided law is so this back to what I was saying in the beginning, so many opportunities that are not evident immediately to people, but they're in-house lawyers, for example, they're doing really interesting work, government lawyers. There's a lot of opportunities out there that are not obvious. And then different law firms, you might not realize how many smaller firms and or going solo and starting your own firm, how many of those kinds of opportunities are out there. But if you if you do good work and then also try to expand your network by helping people being a giving kind of ethical type person, then opportunities tend to come a lot more easily. And then if you're a lot kind of focused on your own self-interest, I appreciate that. I really appreciate coming on the show today, Tim, sharing all of these insights that you've learned and collected throughout your career. Well, thank you so much, Claudio. It was a pleasure speaking with you. Absolutely. And thank you all for tuning into today's episode and we'll see you on the next one.