Owning Your Success, Executive Communication, and the Power of Exposure with Oliver Gleeson

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. Today I'm joined by Oliver Gleason, a former general counsel and COO and the founder of Salient Map Executive Consultancy. Through his coaching and leadership development work, Oliver helps early and emerging professionals build the skills, judgment, and executive mindset that many people spend years learning through trial and error. His career spans from law, business, operations, and executive leadership, giving him a very unique perspective on what it takes to grow from a capable professional into a trusted leader. Oliver, thank you for joining us today. It's great to have you on the show. This is a privilege and your podcast is so big time. Thank you so much for making the time and to start the show right away, I'd love for you to tell us a little bit about your journey. Yeah, so the short version is pretty much as you touched on at the top of the podcast. Today I run Salient Map and my sweet spot is executive coaching for early and emerging career professionals in law. That means helping associates think, act, and perform like partners. But I got here the very long way. I started as a civil litigator in Hamilton, Ontario, Canada, struggled early, had a pretty humbling courtroom experience early on, stepped away from traditional law, traveled the world, lived in Japan, came back into sport and event marketing, wore every business hat imaginable, and eventually built my own consultancy. The thread through all of it is that I kept learning things the hard way and thinking, why did that take me five years to learn? Couldn't somebody just show me? And that's really the business I'm in now, helping professionals shorten that learning curve and build confidence much earlier. So that's the short version. If you want to dig into any of that, I'm happy to jam on it because there's lots of stories and tales along the way. Absolutely. And I'd love to dig a little bit more into that Japan experience. I believe that happened somewhat early in your career. And I believe you had mentioned something about having quite the wake up moment that changed how you viewed success. So I'd love for you to tell us a little more about that story. So I ended up in Japan. So now here I go making it longer. I was a very early adopter. I was a forethinker. I decided to have my midlife crisis very early on in life. It came out of my early civil litigation days. And so now I am rewinding the clock a little bit. I started my career in the last century. So that's how long I've been around. And so before we had Google and before we had the internet and you'd just be happy to get a job. And I was really excited to become a civil litigator. I love the talk. I love the debate. I thought those were my natural traits. And Hamilton had many prominent insurance defense law firms. And that's the world that I lived in. I worked in two different insurance defense firms, great people in those firms. But I didn't love the law that I was doing. And it's something I probably couldn't have known beforehand until I got into it. And really what I didn't like about it the most, and I know maybe times have changed, but insurance law at the time was really negative. Everything was negative. Negative for the plaintiffs. You know, the insurance companies are ripping me off. Negative for the insurance companies. Everybody's a faker. Negatives for the lawyers, all the infighting. It was actually a small claims court case of dog versus dog, which is a story for a completely other day. That kind of put me over the edge. And I said, I got to go. I got to go. And my senior partner was tremendously understanding. I didn't know, Claudio, I could do anything else at the time. I thought this was my career, and I hate to use this term. This is going to sound awful. Like this was my life sentence. This was the only thing I could do. I didn't know I could do anything else. So I thought, I don't know if I can use bad language here, but like, shit, if this is what I'm going to do, I better go see the world. Because I hadn't really done the global traveling I really wanted to do. And I put a bag over my shoulder and I went to 21 countries around the world in nine months. And it was the greatest nine months of my life. It was amazing. And I was getting fatigued near the end of that trip. And I had one of my best friends from university, Canadian guy, Canadian wife. And they'd been living in Japan for four years teaching English. And they said, look, just come up here, teach English. It's really easy. And I went to Japan. And I had no previous connection or cultural connection with the country. I didn't have samurai posters on my wall hanging out like I knew nothing. So I was starting from scratch there. And it was an incredible experience. I built a wonderful life there. And I don't know if this is the story you're referring to, but my life was so perfectly comfortable. I had a great job. I had zero stress. I was in the best shape of my life. And I played university sports. I played on a basketball league with Japanese people and foreign people. And I was at a party and I ran into another Canadian guy. And we're chit-chatting and, you know, I'm in my late twenties at the time. He appears to be close to 50. And we're talking about our stories of how we ended up in Japan. And I told him my story and he looked at me and said, yeah, I just came here for three weeks to visit a friend and here I am 24 years later. And I, like, I almost shit my pants. If you could see my face, my mouth started dropping like millimeter by millimeter until it was this big open gate, big open wide eyes. And I said like, oh my God. And I ran back to my apartment. I called my mother and I said, I got to come home now because it was so comfortable. I thought I would blink and I would be, well, not stuck there. It's an incredible place, but I knew it wasn't going to be for me for life. At some point I had to get on with it. I had to get on with my life, but it wasn't an incredible experience. But I didn't know what I was coming back to. And when I came back, I decided that I was going to do wherever the wind took me. Like I went right back to the bottom rung of the ladder and reinvented myself and latched on with a fledgling sport event marketing company, as I mentioned earlier. And they had seven employees at the time. By the time I left that organization, 15 years later, over 500 employees, offices around the world, including Qatar in the Middle East. And I oversaw that office for a brief time. I didn't live there, but I traveled back and forth extensively. And this company I worked for continues to be an absolute powerhouse in the sport event marketing space globally, a real privilege to work there. So that's the journey from early law up until my consultancy. Amazing. And you mentioned a few things that I found very interesting. You mentioned that it took you, you know, a few different experiences in life to notice and to think of, why didn't I think of that earlier? Why did nobody tell me about that before? Are there some patterns that you noticed there that, you know, about why some professionals advance faster than others? Are there a few specific things that maybe you've learned in this journey and that, you know, I'm sure you apply quite a bit in your current practice? Yeah, Claudio. Absolutely. If I had to pick one word, I would say exposure. And some people advance faster because they get exposed earlier to better mentors, bigger projects, senior people, different ways of thinking and how their particular business actually works. And sometimes that happens intentionally. And sometimes they get lucky because they end up on the right team and in a legal context with the right partner on the right file. And my mistake early on was thinking that hard work would be enough and that somebody would eventually show up with the, with the education plan or just tap me on the shoulder and say, good job. You're being promoted. And that's not how it works. What I've learned is that exposure changes people. You get exposed to something new and suddenly it's like, oh, this is how this works. Confidence goes up, creativity goes up, judgment improves, and then your career really starts to accelerate. It's fantastic. No, I appreciate you bringing that up. I'm curious to, you know, as you work with lawyers, with junior professionals and, you know, with executives in general, what are some things that one could do to bring about that exposition? Are there a few things that one can kind of, you know, take the lead in their own career and try to get that exposition as early as possible, or try to, you know, grow where they are, or maybe, you know, think about going somewhere else. What are some of your thoughts on that? Well, you want to be proactive. Mantra I often use in my training programs is own your own success. And this is advice I really wish I had when I was younger. And I want to be kind to my younger self because sometimes I look back and say like, what was wrong with you? Like, why couldn't you ask these questions? Why couldn't you be more proactive? We always see in organizations and in firms, they have their shining stars, their high potential people. And something interesting I've realized in my experience is that the high potential people, when they're exposed to this new stimuli, continue to grow. But there's a massive segment of the professional workforce that is almost dormant. And when they are exposed, all of a sudden leapfrog the people who are classified as the early high potential. And I see this in life and I see it in children's sports. I'm also a coach of ice hockey here in Canada. And I'll just use that as an example. There are kids who at the age of eight are skating circles around all their friends and they get all the investment and they get all the support. But by the time they hit puberty and they turn 14 or 15, and some of these other kids start to grow, all of a sudden they leapfrog and then they start to get the training and the investment. My point is, is that exposure is really that important for those professionals. If I was to give advice to people, it's to get out of your comfort zone and be as proactive as you can. Try to get into every room you can. Understand why things are happening. Understand the why in everything that you're doing. And I think a lot of young professionals, emerging professionals, particularly in law, is that they're thinking only about the task and they're not thinking about the purpose. So if you want to grow, if you want to move ahead, don't just ask what you're doing. Ask why you're doing it. Why this email? Why this report? Why this meeting? Why this research? The lawyers and emerging professionals who stand out aren't just doing the work. They're trying to understand the world around their work. They understand the client. They understand the business. They understand the business of the firm. They understand how money comes in the door and how money goes out the door. And again, looking back, one of my regrets is that I just wish I asked these questions earlier or knew that I had to ask them because the people who accelerate their careers tend to be the people who are curious enough, excuse me, to understand the bigger picture and ask these questions. What do you think is usually missing when it comes to, you know, our education, maybe our legal training in the sense of what, you know, law school can expose us to? Sure. Like, I guess starting with law school, I'm so far removed from, I actually just had my 30th anniversary a couple of weekends ago, law school, that's how long I've been out of law school. There's a lot of conversations happening on LinkedIn. I'm sure you've seen them where people are talking about where the shortfalls of law school are. I think I would leave that to those audiences because I'm not close enough to it. I didn't have a big problem with law school. We all left law school knowing that the law sort of, law school taught you how to think. They taught you some generic concepts about the law contracts, torts, all that good stuff. But you knew that you were going to learn on the job. And I think at the time we sort of just accepted that. I think what's missing from traditional legal or corporate training, a lot of the time is just the training itself. And I don't mean that as a criticism. I'm just going to talk about law now, because that's our audience. Partners care, leaders care, firms care, everybody is busy. They don't always have the time, expertise, resources, support. And what ends up happening is that people learn the executive part of the job, what I call the osmosis model, right? Watch, guess, try, get corrected, try again, hope you absorb it, figure it out in the hallway, read the room, learn through proximity. And look, we all learn it eventually. It was the rite of passage, but we learn it the long way. And it's grossly inefficient. And my view is that these lessons can be taught much earlier and much more intentionally. And when they are taught earlier, everybody wins, right? It's not just the participant in the training program. If a firm was having questions about, oh, should we be investing dollars and cents in training? And I'm going to take a very cynical view for a moment, so please excuse me. And if the leaders of these firms were the greediest, most selfish people who wanted to make the most money imaginable, the best thing you can do is train your people. Get them into revenue producing mavens for you now, earlier, right? Free yourself up, get out of the weeds, because they don't have the time to do the training. I want to be really careful and choiceful with my language because I am not blaming firms at all, at all. I want to emphasize again, they care for people. And sometimes the firms, and there are some firms out there, some of the big ones especially that have really robust training programs. Obviously in the work that I do, I have these conversations. And with some organizations, yes, thank God you're here. And other organizations, other firms like, no, we're good. This is what we do. And it's, oh, tell me about it. And I'll say, oh yeah, that's great. Congratulations. And really beneficial for the associates in your firm. But taking the blame away from the other firms, a lot of the time it's really well-intentioned. They have intentionality. We're going to do this training and then something comes up, something gets in the way and it just keeps getting pushed and pushed and pushed. But for some of the firms that eventually do get to it, what also happens is that they realize, well, it's not, it's not that good. Like newsflash, training, teaching is an actual skill. My mother, she was a teacher, a high school teacher. She always wanted me to be a teacher. I love teaching. I've been coaching my whole life. It's natural to me. And I never went into teaching because when I was a younger guy in the nineties, I said to my mom, I love teaching, but you're capped. You're capped on what you can do. You're capped on what you could make. I never believed at the time you could build an online business that can scale around the world. Right. But teaching is a real skill. And sometimes in sports and in business, people who are best at a craft, best at an art, they take for granted what they know so naturally, they can't translate it to the people who really want it in a way that's effective and impactful. And then other times, if a firm says, Hey, let's look externally, well, who do you talk to? Who's Claudio? Who's Oliver Gleason? How do I know? What do we bring them in? What's their curriculum? How does it work? Is it going to give a return on my investment? So that's also a bigger challenge for firms because they might not have the right person who knows how to vet these opportunities or know where to go. And so it kind of gets stuck. And so for some emerging associates, it really can be luck of the draw. Where did you end up? What's their development program? Like how intentional is it? It really, really starts with a commitment to training. And if it's not internal, a commitment that we're going to find it and develop these people because it works for retention. It keeps people in house and it's a big problem now in firms particularly. It's a strategic risk with a lot of firms. And if the concern is, well, look, we're going to train them so well that they're going to go off on their own, well, you know, wish them luck. And you said they went out on their own and every top law student is going to say, I want to come to your firm and I'm going to work my ass off because I know you will develop me. And in the time I'm there, I'm going to be so revenue producing for you that you're going to love me. So it's a, it's a training everybody wins. So we just got to get that commitment. And when we lean in hard to learning and development for your associates, it really is wins across the board. I find it interesting that it really takes a little bit of a commitment that goes both ways, right? From the organization to invest into trainings, but also from the people involved in it to go ahead and seek those opportunities and try to take that from driver's seat as we had said. Otherwise it really kind of stays up to fate or up to the luck of the draw. Coming back to the focus of today's conversation here, I also understand that some of your, you know, posts on LinkedIn, some of what you teach as well has to do with communication and presence in professional growth. What does that executive level communication look like? Yeah, that's funny, right? It's such a term that depends on who you're talking to on what day, what time of the year, the angle of the sun, moon's gravitational pull, you know, what communication means to people. I don't think executive communication gets misunderstood. Many people think it's about how you sound, and this is coming from a guy who likes to talk a lot, right? It's about sounding polished and sounding smart. And I don't think that's it at all. The question I always come back to is this, did it do its job? Did it do its job? Whether it's an email, a report, a meeting, a conversation, every piece of communication is a transaction that has a job to do. Did it create clarity? Did it answer the questions people actually had? Did it move things forward? One of the concepts that I teach is user experience, UX. We use it in technology, but I believe there's a human form of UX. There's a user experience of Claudio. There's a user experience of Oliver. It's a feeling. What's it like to work with you? What's it like to receive one of your emails, Claudio? Be on your podcast, attend one of your association meetings. Every piece of communication leaves a residue. And over time, this becomes your reputation. So that to me is executive communication. It is the job of every transaction you are doing. And fairly or unfairly, you are being judged every day by every stakeholder based on these thousands of micro transactions, these micro communications. So if you look at everything that you're doing with that sense of pride through this user experience lens and say, what does it need to do? And if it is doing its job, that is C-level, that is partner-like, that to me is executive communication. I try to really focus the podcast on early career professionals. Many young professionals might struggle with the confidence and decision-making under pressure, especially because of all the, you know, hand-holding that you're used to getting. And then it just comes to a point where you're kind of expected to make decisions, but at the same time, you're never clearly told whether you're allowed to or not. As you were setting up that question, I was raising my hand to the camera because you were describing my early career to a T. And I was an emerging career professional about five times over when I was at the sport event marketing company. We kept reinventing ourselves, getting ourselves into new environments, new spaces. And it felt like starting all over again. And so I understand that feeling. So it takes me back to my early career trauma of being in the courtroom as a young lawyer. I remember being a young lawyer and being in the courtroom and I was so ambitious and I was so excited to show off my talents. And we were, it was at motions court and the courtroom was jammed. All the lawyers were there. Everybody's client was there. And the lawyer that was on the other side was a lawyer, about 10 years experience, but other lawyers made fun of him, called him like the town imbecile. And I thought it was going to be a slam dunk. And he absolutely wiped the floor with me. And I was, I had knots in my stomach. I was having a panic attack. The judge was yelling at me in front of everybody. And I just, I just had to get out of there and eventually got out alive. And I remember just that frustration that stuck with me. And any opportunity I had as a mentor from that day forward to teach somebody something that took me five years where I could say, look, this took me five years to learn. I'm going to teach you this in five minutes because it's not that complicated. I do that. But as you described earlier, especially that phenomenon inside of firms where two different people can have a dramatically different experience. Who had the Claudio as their mentor that did that and said, I'm going to tell you this in five minutes. And who was left figuring it out on their own. So I'm going to try to address the figuring out on their own. And a lot of confidence problems are really boiled down to understanding problems, just understanding things. And when I was a young lawyer, I often lacked this confidence because I didn't fully understand where my work fit into the bigger picture. Quite often we're working on a piece of the puzzle, but nobody shows you the front of the puzzle box, right? You don't even know where this piece is going. So the more context you have, the more confidence you have. Where does this work go next? Who uses it? Why am I doing it? What happens if it's wrong? What happens if it's great? When you start understanding the bigger system around your work, decision-making gets easier because you're not operating in isolation. So it comes back to this owning your success. You just need someone to tap you on the shoulder to say, you got to find your answers. Don't work in a silo. Don't just work on the task. Don't just read the medical report. Know how it fits into the puzzle. You have to sometimes build the front of the box by yourself. And that's hard. This is the advice I'm giving to people who I can't train, who don't have training programs at their firm, who are like, shit, I'm on my own here. Thanks, Oliver. But what do I do? You just got to get into the rooms. You got to find out, pull aside the partner, pull aside the lawyer, say, I need to understand this for 10 minutes. And it makes everybody better. And particularly when it comes to finance, if you're in a firm or you're in a normal corporate environment, whoever the finance nerd is, and I love them, I love nerds. No one ever talks to them. No one ever gives them the love. They can't be more excited when someone says, what's a P&L? What's a profit and loss? Like they'll say, oh my God, you've made my day. How much time do you need? People have an inner mentor in all of them. So if you can go out and find out what your work means and where it fits into the world around it, you will become more confident. Your decision-making will be sharper and you'll have more confidence to ask the right question at the right time. And your partners will love you because your work will become more partner ready. They're out of the weeds. They're working on more strategic files. And eventually you could follow along and learn what's up with that strategic file. Who are the stakeholders? Who are our clients? How does their business work? Just curiosity, curiosity, curiosity. And if you can be motivated in that regard and don't get boxed in isolation, you're really going to accelerate. And this flywheel of confidence will develop. And you are really going to move up your emotional, physical, intellectual, academic, professional ladder exponentially. If you think about it, a young lawyer who's starting out today, and is there a specific piece of advice that you would give them if they wanted to stand out and build a strong career from day one? It's again, understanding that why in everything you do and understanding the business of law as fast as you can. Understand how the firm works. Understand how revenue is developed. Understand how clients come and clients go. When I was young, I was so naive to all of it. The senior lawyers would hand me a file. They'd put it on my desk. I thought there was a magical mountain called client mountain and like little gnomes. They came down on skis with big long white beards and a file and they'd say, here's your next file. I didn't even understand how it worked. And sometimes we're just too nervous and anxious. We're just happy to have that job. Now a lot of us could be more self-starting today. There's a lot of resources like, Hey, Google's free, AI is free. You can really educate yourself, but find the leaders in the firm at every level and ask them a simple question. What would you do five years earlier? If you could go back in time, what is one thing you would change? Ask that to the lawyer who's been practicing for 25 years, 2015, 10, 5, 3, and you will build a really fast library of do's and do nots, particularly in the specific context of where you are working and living. So my advice is general, but universally applicable. Taking this path is laser focused on where you are, where you live and where you work. Amazing. Well, I really appreciate you making the time to come on the podcast and share this really valuable piece of advice with everyone. And thank you all so much for tuning into today's episode. Claudio, thank you. On behalf of everybody, the work you do is amazing. You're serving an incredible international population and everybody is better for your efforts. So thank you, sir.