Leadership Strategies: How Hugo Gatsby Cultivated High-Performing Teams

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Hugo Gatsby is an award-winning designer, having been voted a top 40 graphic designer in North America. Having worked in digital media for over 15 years, Hugo leverages UX design, behavioural science, gamification, and design thinking to develop AODA/WCAG compliant websites, build authentic brand stories, and genuinely connect businesses to their consumers. He has collaborated with companies such as Deloitte Canada, the Bank of Montreal, Bell Canada, Jean-Paul Gaultier, Volkswagen and even Netflix.

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Host:
This is Hugo Gatsby. He's pretty much many things in one. He's an artist, a former physicist, a current consultant, and for the second time, a father. He's done many interesting things. He has managed the private art collection of the Thomas family, managed campaigns for Hilton Hotels, Toyota Motors, and the City of Vancouver. He's also a digital media professor for the Visual Arts College of Design and Art in Vancouver, and he currently runs Stradia Design Labs and consults for Deloitte. I'm going to assume that's all true.

Hugo Gatsby:
Yeah, I guess the only thing is, I went to school for quantum physics, never really got into physics, like became a physicist, but did get to work with NASA for a while there. So, I feel like it’s true, but I don’t know if someone’s going to do fact-checking and be like, “He wasn’t actually a physicist.”

Host:
Well, I think it might be underselling. Yeah, once you work for NASA, you probably knew a few things.

Hugo Gatsby:
No, yeah, no, no. It was really a wonderful experience. Probably, I still say it’s probably one of my favorite companies I’ve ever worked with. Absolutely loved them. So many wonderfully nerdy and cool and creative people all in one. And it just, it always... I always felt like I had to prove why I was there, but it was fun. It was so worth it. I still talk to my wife about it. I remember getting a letter from them weeks before our wedding, and I was so excited, but I couldn’t tell my wife about it because it was part of a surprise for her wedding gift. And she’s like, “I hate when you do these things.” Working in NASA’s surprise wedding gift... 

Host: 

That’s an interesting way to put the structure for gifts.

Hugo Gatsby: 

It’s a very long story. It took about 18 months. It was an 18-month kind of process of working with them on something very small but wonderful. So yeah.
Cool, well, I'll start off with something that was interesting to me about you, which was that you were non-verbal for a bit longer than most kids, and that probably might have been kind of, if nothing else, a unique experience. But I'd love to hear a little bit about that because I think it sort of permeates through how you perceive, I guess, communication and some of the things you’ve done over the years.

Yeah, that’s, I think that’s actually the reason I’m in the world of communication. It’s because I’m on the spectrum, diagnosed with autism at a very young age. I was non-verbal, had speech pathologists, speech therapists all throughout my younger years. I think in grade four is when I had a bit of a... call it a mental breakdown. I don’t know if it was like an... in like they call it stimming in autism, but it was like stimming to the highest degree. I was able to start talking afterwards, but I had lost a large portion of my memory of just about everything. So I understood words, I understood sentences, I understood math, I understood all these things, but I didn’t know how I knew them. And that’s when we moved to a new city, and I just kind of restarted over.

My mom, being a single mom, you know, worked her butt off to support three kids. She was amazing, but didn’t have the time or focus to focus on just one of us because she was trying to keep us living, let alone having to deal with these things. So I was kind of left to my own devices. I remember moving to the new city, and the first thing I did was read a dictionary because I didn’t understand how I knew words. So I wanted to know what words were, and I just read through the dictionary. Eventually, I found the word “word,” and I was like, “Oh, this is what they are. Okay, this is how I understand it.” It was kind of a choose-your-own-adventure, and that’s kind of led my whole life into this process of, you know, being able to communicate, being able to share ideas, being able to figure out things I don’t know, and understanding how to solve them. That’s been my whole career as a strategist, as a consultant, as just about everything under the sun — just, you know, finding a way.

Hugo Gatsby:
Right. So, I mean, one of the things... there’s two things: First is... what... you know, what...Exactly is stimming and um, the other... yeah, if you could explain that a little for the audience a little bit more, because I think, uh, yeah, stimming is... so it's essentially stimulation. So you'll notice that sometimes I might shake my hands or twitch my head or there's some sort of, like, mannerism, some sort of just physical reaction to the way that something is happening, and it's very common with people with Autism, ADHD as well, even people with certain cues for depression and things like that. And stimming is a term that we use in autism to show that there's some sort of involuntary reaction to something. So if I have an issue with something, a lot of people will just internalize it. With autism, it's a little bit different because you might not know how to say something, but your body will physically react to something and that's that sense of stimming or stimulating or over-stimulating, I guess it could be. But one thing that's interesting to me is, you know, this idea of, you know, expressing yourself... how did that part of your life, you know, inform that? Right? Because there are different ways people are creative and the different reasons why they're created, but how did this, you know, you literally couldn't communicate to some degree, but then how do you see the value of self-expression? Some people don't even... don't really value that at all, and some people think some people only commit to that, right? 

Host:

So how did that affect you? How did you see that? What's your value structure on that?

Hugo Gatsby: 

Uh, that's... it's a little bit of a story and there's a... I'll go into like the Kohl's notes version of it, but basically my mom met a guy, became my stepfather, who was like the most influential person in my life and he did everything. He did everything for me, like sent me to military school, sent me to France, we built a 1967 Mustang together before he passed away when he had a brain tumor. Like, he made me understand the potential of myself. And when he sent me to military school, I understood what leadership was. When he sent me to France, I understood what creativity was. And I didn't take art or math classes a lot during school just because people didn't know how to react in our class, so I was just kind of left to my own devices and given other courses and then math because I was really good at it, they’re like, "Yeah, you don't need to take it, just write some tests and that’d be done." So I didn't really get into art until university and I went to my... went to university and found this world of art because my brother was teaching a Photoshop class and I fell in love with it because I didn’t know how to communicate with imagery. I've seen museums in France for art, and I thought that this was just this majestic thing, but again, at 16, no one explained to me basic concepts of, you know, what right or wrong is or what lying is or, you know, what art was. I just... I just saw these things and appreciated them for what they were and it gave me like a sense of feeling inside that I never had. And then when I went to my brother’s class one day, Tiang, I fell in love with Photoshop and then my world became colorful, and that was like into my 20s where I first started to actually get into art. So, yeah, it was... it was a weird relationship with creativity and me. I had an opportunity to go to Fashion School in high school. My dad was like, "Nope, my son’s going to business school, like, I trained you, I trained you well enough, you're going to business school, you're not going." And I had a scholarship for fashion school because I took a class because I didn't get an elective. I had already taken all my classes and graduated before I was in grade 12, because I moved to France, did a bunch of extra classes, so I had this opportunity just taking a bunch of extra stuff and that was the only class available, so I just took it and I loved it because it was me allowing my brain to work in different ways, which never really was thought of for someone like me.

Host: 

So you said that you... you had to figure out what right and wrong was. Is it... was that just sort of an offhand comment or was morality an idea that you had to, like, sort of... that was foreign to you and then you had to structure? And I’m sure you weren’t like breaking into houses, but, you know...

Hugo Gatsby: 

Nothing like that. It was like when you're a kid you're taught, you know, the ideas of like what right and wrong is, how to say please and thank you, you know, courtesy, what knife, fork to use, things like that. Because I lost my memories, I didn't... I don't remember any of those things, so I had to relearn those things at a much later date. So even though I was 16, I pretty much had the mentality of a six or seven-year-old and that's what I meant. Like, it wasn't... and my stepdad, again, kind of gave me, you know, very great values and structures that I still use as like rules to guide my life in a very, you know, positive way, but I didn't understand those things. And then it was just more of an offhand comment than anything.

Host: 

Fair enough. So, uh, when you went to France, what... yeah, is there a piece of art that you remember that really made you feel like, hey, this is, you know, sending me a message or communicating to me in a way that's unique, that I haven't seen before? Or was it just that whole experience of, you know, a lot of people talk about how France really affects how they see themselves and things of that nature? Was it just... or something like gradual there was a mark. Rothko painting that I saw in our Mark, yeah, Mark Rothko painting in Grenoble and actually the image behind me is based off of a Rothko painting itself but I fell in love with it. It was simple but it was creative and I remember living in France and it might sound weird to say this but there was a moment where I was walking down the street and I felt that that particular moment that no one was thinking of me at all and I just knew and I felt invisible and that feeling gave me such a sense of purpose and meaning and I don't know why because it made me feel insignificant but I felt so powerful in that moment as well and I think that was like the creative outbringing of what France did for me. It made me kind of reform my identity. And that's actually how I got the name Hugo, by the way. I got the name Hugo living in France and when I moved back home I told my stepdad about it and he's like, "Yeah, we won’t tell your mom but I’ll call you Hugo." And then when he passed away I actually started going by Hugo. Like the day after he passed away I started going by Hugo and I was like, "Nope, that's it, done, end of story." And then when my wife and I married, she's like, "He was going to be your first name now, not Daniel John, because you hate being called DJ." I'm like, "I do hate being called DJ." I'm surprised you didn’t go into music after that. Yeah, DJ Hugo Gatsby would have been a great freaking name, right? It’s just so overwhelmingly epic. Yeah, I know. So I loved every moment of the France experience, but I think the art—it’s not one piece that I saw. It's just a feeling that I had, you know? And I can’t describe it more than that. I think if anybody ever has a chance to live in France, go. Just go to France, live there a week, a month, a year. I don’t care, just go. I’m trying to like convince my wife to move back to France, actually. My friend and I want to buy a place up there, so we’re like, "Let’s go buy a place in France and become like secret celebrities or something." I don’t know. I don’t know how it works out there, but we can figure it out. You’ll figure something out.

Host: 

So one thing you said was not being watched made you feel more powerful, I guess, more... gave you the opportunity to feel more free, I suppose, if I’m going to summarize it right. So is that... that is kind of weird, right?

Hugo Gatsby: 

So what, you know, people... most of the time I guess it is weird and isn’t weird, right? But is there something about... do you find freedom in isolation? I think I’m a very isolated person to begin with. I think my brain is a very kind of solitude-oriented place. It processes things at a very different pace. And I think, you know, I’ve always loved quantum physics even when I was a kid in school, like elementary school, working on projects of like space travel and life on planets and moons and things like that and figuring out the probabilities. So I think when I think of that sense of isolation, it’s actually liberating. I think if you can’t be happy by yourself or love yourself, you can’t love or be happy with anybody else. And for me, it was always a matter of understanding who I was. And I still don’t quite know that, but I’ve tried just about everything. The way I relate to people is through experience. I’m terrible at communicating. I feel like I’m awkward, socially awkward. I just... you know, I have all these kind of negative qualities towards how I am with people. I’m very intense, I feel like. But if I can relate to people through some sort of experience, it builds a bridge. And I think that’s how I’ve lived my life. But I’ve also been able to experience just about everything under the sun because I’m always trying to find something—some meaning in everything that I do, some purpose. And I always kind of feel like, you know, there’s certain elements that relate to certain people that I meet and it always makes me feel a little bit more connected to them, even if they don’t know that well. In terms of communicating, I don’t think you’re doing too badly.

Host: 

Thanks. I actually really appreciate that. And, uh, you know, I guess speaking of building bridges, something that, you know, I wanted to point out is that the way you started finding ways to express yourself is through technology and particularly through Photoshop. So I want to ask you how technology actually affected your sort of, I guess, career generally, but how did that allow you to, you know, sort of move things forward?

Hugo Gatsby: 

I mean, I can’t have a meeting or interview about technology and not include rollerblades and the movie Hackers from 1995. And I know friends of mine are watching this video, they’re going to laugh and roll their eyes because, "Jesus, you always bring up..." I find a way to bring this up. But I think, you know, I was in grade eight when Hackers came out and I had just gotten a 486 laptop or computer, rather a desktop, and I got a 386 laptop right after the movie came out. And I was in love with this language that was binary and I loved to understand how things work so I just like took it apart and rebuilt it took it apart rebuilt it um I actually would um splice phone line cables from all of my neighbors so I have internet access at our house and be able to like get everybody else's passcode so I can get free internet for my family we can still use our phone I was I was really into the technology I really loved the idea of meeting people that you never see I love the I love the internet in the early stages of it I mean even the early stages of social media and and all that technology was just something that I was scared of and excited for simultaneously and if I had the people in my life who understood the technology that could have promoted me I think I would have been a much different place but I did with it what I could and what I felt I needed to at the time and I've always kind of went I went to the art route went to the design route went to the business route like and now technology is all around us and and I feel somewhat comfortable more comfortable than most but I also worry is what my kids are going to be like when I'm 60 and they're in their 20s and they're gonna be like yeah Dad you don't understand these things I'm like I helped create these things kid like what's wrong with you

Host: 

Well speaking of business technology and uh sort of an art can you talk to me about your experience rebranding the Hilton Hotels

Hugo Gatsby: 

Yeah yeah that was actually that was a really fun project that was very early on in my career back um when I was working in Vancouver and they wanted to create more of a lifestyle branding and this is my big Forte into into strategy development so what they really wanted to do is reconfigure their brand for a luxury brand but also make it affordable and what kind of came out of that whole process was what is now their kind of Hilton's point system so what we saw was a lot of people will stay there but if we reduce the price of staying overnight for certain people and increase the price for people who are willing to pay more to stay at the higher levels of the of the buildings people are more inclined to actually do that because there's a there's a very clear definition between you know lower class and higher class income and and that was the kind of visual element of it that's where the strategy came from and then that that middle ground was all of the clients that wanted to go on the point system that had some sort of benefit and you know we got to stay there we got to stay at hotels we got to work with our team we had some really fun experiences with it the health and brand itself has just been super amazing my wife is actually a Hilton member um which I found one like I started dating her years later and she's like killed member I'm like oh I love hell just like I'm one of the healthy members of this thing I'm like I helped create that and she's like okay yeah sure and then I explained to her and she's like oh seriously I'm like yeah yeah so it was it was a really fun experience a lot of learning a lot of mistakes along the way I think I think you know to grow you need to you need to be willing to try new things but you need to be willing to fail and and fail in a way that you can recover and improve and I think that's that design thinking methodology I had that you know very early on in my life I always thought I'm always it's always going to be a little harder for me to do things just because of who I am how I am so I understood that and although I get frustrated I think when I see it through I get a much bigger high of like I was able to do this I was able to like you know create something or build something or see something through that didn't exist before and it was it's nice to see where it is now and how it's kind of blossomed into this just epic um world of of travel and tourism so you

Host: 

You know I like to even dive even uh sort of deeper into it so because a lot of it is also leadership and some of the stuff you learned in military school mixed with all the things you already talked about so you know it being a big project and a really difficult project how did all those things intertwine and what are some of the challenges you faced uh you know and because I'm seeing that you're able to increase uh sort of the value to over 15 at that time and so how did that you know what are the different steps that uh you're able to take or or retake that allowed you to sort of uh to put it in this position

Hugo Gatsby: 

Yeah great question great question I think one of the things for me was when I was in military school I had this commanding officer and he gave me two really great pieces of advice the first was lead by example if you can't do the work you can't expect people to follow your order uh and the other one was teach others to leave and Inspire them to stay that is the single most important role of a leader and it didn't and it was actually during that time at that company where I understood that and you know deadlines everyone has deadlines that are almost impossible to me and I think during that project there was a lot of deadlines a lot of expectation you know we we didn't budget the project correctly we had so many late night like work hours people are getting burnt out so I took kind of the burden and did a lot of the work myself kind of pushing it Forward figuring things out working on like forecast modeling how like again my brain worked in a different way so I could figure out these things just on the Fly.

But what ended up happening was the team saw that I was staying late every single night and there was this huge deadline and I was like alright guys have a great weekend you know we'll talk soon I remember you know just wishing them a really good weekend and they all they all kind of sat at the door for a second and I'm just like running around was like did anybody forget anything can I get you guys anything and they're like no we're fine and they just sat there it was like lingering for like a good 10 seconds I thought it was weird it was like I got too much I got too much stuff to do uh and then they left and I was like working working and then all of a sudden the buzzer comes on and I open the door and it's the whole team with dinner and they're like we brought you dinner I'm like thanks we're gonna get this done tonight and we stayed until like the early hours of the morning to get like that major project done and it made me realize that I'm the kind of leader that inspired my team to stay because I was always putting them first putting their needs putting their feelings first we made the deadline and then it came back with revisions which again was like a bit of a blow to us but I was like guys like we did we did The Impossible and their feedback is only to make it better but we did the impossible so anything we do from this point on is a success and they were like yeah that's a great mindset and one person's like stop being a Hallmark card it's like I remember it's like stop being a Hallmark card and let's just let's just be angry for a second I'm like and then I actually went out and bought laser tag uh sets for everybody and then we played laser tag the next day to kind of like vent and everyone's like this is this is hilarious but that was that was a single defining moment where I realized the kind of leader that I will be and that I am um but yeah like that moment that like those moments and that was what 2009 2008 2009 around that time uh and it still stays in each of the state like I still remember clear as day I it just been such a fun experience.

Host: 

Well that's amazing and I think you know one thing that's coming to me with this is that uh because you've been in all these different kind of areas right you've been in places where you have to be very quantitatively sensitive at a high level and then very creative at a high level and sort of mix those things together and then also be in a business mindset so you know with all those sort of all those experiences and things of that nature uh you know what is now your concept of value because at least in the creative world it's is ephemeral but um at the same time you know with it with an understanding with a quantitative mindset you know whether you applied or not you do have to think about it so what is that how does that involve in your mind how does that end up being uh when you're thinking about outcomes.

Hugo Gatsby: 

Yeah that's a that's a great question uh so value to me is this equilibrium and and there's always three sides of equilibrium there's there's the client there's you and it's whoever the client is serving which is technically their customer um and it could be it could take any type of shape it could be you know government helping you know cities or a company helping a particular customer or you know some sort of like software helping an education system whatever but everybody has to walk away winning equally and I think the challenge is everybody's always trying to come out further for a buck like everyone's trying to make as much profit as they can and and I know I'll probably get like negative backlashers but I I think I think profit's good to an extent but I think there's a certain point where numbers don't make you any happier and you know when I was when I was in Harvard I was able to go and do like some behavioral Finance work and I met some amazing props and we always had these discussions about what is what is happiness what is the number for happiness and it ended up being like a very small number I think a range different conversations range from 50 000 to 80 000 is the number that people need to be happy with but when I kept that in my mind I was like well how does everybody walk away being happy so when you work with a client you want to make them happy and provide value what that outcome is going to be and and your price should reflect that but the price should also be something that you're happy with and those two things have to deliver something to that that customer that client's customer that makes them happy and if one of those parts aren't working then everything falls apart and and I think that you know the unions in Germany specifically do a really good job with this where unions in Canada not so great over in Europe a little bit different it's the organization the government and the union all have to work together so if one person's not performing let's say the company's not performing the union goes to the government and they kind of gang up on the company say be better if the government or the Union's not performing the company goes to the government saying like let's help fix this Union the union has to fix up and they become better um and and I like that concept that everybody has to work together to succeed because that's really what it is everybody needs to equally feel value and not that they got cheated out now if you consciously say this number that I want but I'm willing to take a little bit less to make them happier that's that's your prerogative that still makes you happy cool but I think when people shortchange themselves and I did that. For years, I would try to get a project by cutting my Polarises, cutting my prices, and it was just exhausting. Because, you know, at a certain point, I was doing websites for five thousand dollars a pop, and the amount of work I had to do was insane. Um, and I ended up keeping track of all of the problems since, and I basically made what I called an ill-fit Persona. So when I go into a project now, and there’s a certain kind of criterion of questions I ask myself, and these clients get to a certain threshold, I’m like, "Guys, unfortunately, I don’t think we’re gonna be a great fit for each other, and this is the reasoning as to why. If you want, I’ll help you find a person that’s a better fit for you as a client for working with, but I honestly don’t think that it’s me, and I don’t want to waste your time or my time."

Hugo Gatsby: 

Yeah, and people... I wish they would like that more than they do, but I think they get offended by that. And I think it’s because I’ve done, you know, over probably at this point in my life 150, 200 projects. I know, I know, like I know what good looks like, and I know what bad looks like, and I’m pretty good at picking out those between those two now.

Host: 

So, you know, that’s sort of a bit of a... kind of it’s a hard thing to, you know, to pick out. Obviously, we, you know, we kind of have the same thing where we try and be very careful with who we’re providing value for, because, you know, I just... to something we don’t know how to tone it down to give less, because it’s just not something that we do. So we try and be very careful with saying, "Hey, we’re doing this, but we’re going to give you everything we have to make sure you’re happy, but you have to... um... but it can be a take-take relationship because we are working together. Your goal is our goal, because, you know, we have the same place we want to reach, but we need to make sure that... um... that no one’s losing out through this."

Hugo Gatsby: 

Yeah, and the only way we can really lose if is if you don’t give as much as we’re giving you, and we will do our part. We do everything to do our part. You guys have to do that on your side. And also, you know, and basically good faith is a very, very big part of that.

Host: 

Definitely want to work in good faith, you know, so I...

Hugo Gatsby: 

Right, and that way it makes it fun, right? Because when you, you know, just like the story you gave where there was a bit a few revisions here and there but people sort of did all this work, we want to be in a position where if people are given their all, they feel like that prize at the end of that journey is a real prize, and it does go somewhere. So I understand where you’re coming from completely. It’s a big part, it’s a big part of what we’re trying to do as well.

Host: 

And funny because you talk about prizes, you know, gamification has been a big thing for my life. Like, um, when I moved to the new city after like my kind of verbal kind of Enlightenment, I became diabetic. So early on in my life, I had so many, you know, doctor’s appointments and medical conditions and all these things I had to deal with. I started to gamify my life and saying, you know, like, if I got to this certain point, if I control my blood sugar to this level, I would treat myself to this or if I was able to, like, you know, make a new friend, I would, you know, do this as a way to celebrate and little and I’ve gamified my life the whole way.

Hugo Gatsby: 

And I think that reward system is very, um, very incentivizing for people to do things, and it’s not just giving them gifts and things, but making people feel important, giving them a challenge, being a mentor, being a guide. And I think, you know, those elements of gamification, everybody, everybody uses gamification, but I don’t think people know it. And that’s one of the things that I absolutely love when I bring it to the table and I say, you know, we’re going to look at your strategy. I’m gonna break it down into like gamification approach. I’ll be reading news, gamification, it’s like, "We don’t, we don’t play games in our organizations, like it’s not games." Gamification is a scientific process of how you actually, you know, quantitatively reach milestones, and you’re already doing that given, and I usually give them analysis and I’ll say, you know, I’ll do a free analysis if I need to, to kind of like show them what’s happening. It’s like, "This is why it’s working, this is why it’s not working. You have, you know, eight tactics you’re using out of like the 64 that I have, but eight of them are all in like one category, but there’s eight different categories, so you’re missing seven different categories, and if you just include one thing from each of those other categories, you’re going to change the way that your organization works."

And I love, I love repurposing old technology and old tools, you know. I’ve worked for banks and telecoms and media companies, and they’re always using super old technology. Like, I remember we’re working for Bell, and I think, I think we’re running on, um, Office 2000 and whatever it was, 2008, 2000... something like that, one of the older versions before they went to like 365, but it was like two or two generations before 365. So they couldn’t even just upgrade to 365, and I had to make everything work with them, and I’m like..This is a nightmare, but I figured it out and kind of made it work because that's what they had available to them. They didn’t want to use new technologies to make their job easier. And even though I said to them, you can't move a mountain with a voice, so I just had to slowly make my way to the top of it and then get it shown to them, everything done there. And it's like, now to make it better, we can do this other thing. And we're already at a point where once we transfer over to two generations up, this stuff will still be pliable in that new system because of the architecture that I made with it. It was just like, you know, a rabbit hole of research, blogs, and things that I talked in communities about, people, Reddit posts, and things like that. So yeah, lots and lots of relationships. Lots of... I mean, if people think nepotism doesn't exist, they're wrong. It is, you know? The nicer you are to people, it’s exactly it. And that's how the world works. The nicer you are to people, they're going to return that favor in kind. 

Host: 

And that's how the world works and it should work. Because if you're not willing to take the time to be nice to other people, why should they be nice to you? That's how I look at it.

Hugo Gatsby:
No, I think that's really important. And I think even when we're talking about gamification, we're talking about people. A big part of like some of the things we see is, hey, you know, everybody has their own way of rewarding themselves and seeing what is a reward to them. And a lot of what it means that, you know, because we are definitely trying to build projects and we're definitely trying to, you know, bring people together to bring that. And, you know, our capital is the quality of the people, and a lot of that is, you know, structuring things in a way where each individual's perspective of themselves is attached to that project. But also the way that they are rewarding themselves. So some people want to do a lot of work regardless of the creativity. Some people are only happy because they did something new. And how do you structure the way that the outcomes of that project—how do you structure the outcomes of that project and the pieces of work in that project so each individual is rewarded all the way to the finish line, right? And then there's opportunity for gamification all the way up and down this, you know, sort of the ladder of contribution. And a big part of, you know, leading a team towards an endeavor is making sure that you sliced it as well as you can, right? And people's goals change over time and perspectives of themselves change over time. But, you know, being able to, you know, essentially make it modular, make it personable, and make it fun, as the idea of a game implies, is a big part of some of how we see things, right? In terms of, you know, pushing things forward for our clients and pushing things forward for our teams as well.

Host:
I love that. I absolutely love that. And I wholeheartedly agree. And you're right, like that evolutionary state is part of that gamification approach. I think the challenge is leadership. I think a lot of organizations suffer from... 

Hugo Gatsby: 

I don't want to say poor leadership or poor management, but I think it's more management than it is leadership. Effective leadership techniques emphasize understanding how your team is going to perform and adapting your style to accommodate them. A leader's role is to support and elevate, not demand that everyone change to accommodate the leader. This approach helps build trust and promotes communication in leadership as the foundation for genuine, open dialogue.

A lot of large organizations face issues because they prioritize structure over connection. For example, in hospitals, banks, and major corporations, you’ll often find negativity among staff, even while these companies win awards for being "best places to work." The pay-to-play system rewards optics, but we need to focus on cultivating high-performing teams by genuinely meeting employees' needs. Research from England shows that offering a four-day workweek—about 32 hours—can create slightly higher revenue while massively reducing burnout and depression. This shift doesn't mean working less; it means working smarter, with team empowerment strategies that increase engagement and allow people to take control of their work-life balance.

Today's generation has the opportunity to lead this change, showing that accountability in leadership is about responsibility to the team, not just to shareholders. New technology, including AI, is helping us work more efficiently, and I’m integrating it into my work to stay relevant. Convincing my dad of this shift, as someone from an old-school mindset, is often a litmus test for me. If I can persuade him of a new approach, I know it’s sound. His resistance is sometimes frustrating, but it helps me refine my ideas, which ultimately benefits everyone.

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Host:
So I'm assuming you learned a lot of that leadership stuff uh and specifically the leadership stuff about leading by example from the military school that you had and you did say that so you know one thing I always ask the people who come on this the sort of podcast is you know how do you scale your you know your perspective on leadership so you know you have 500 people and they can all see you and they can't all see the example you're giving because you are only so much no matter how productive you are as an individual so how do you how do you push that down an organization right how did you get to the top of that mountain and what is it that cascaded down to the bottom that uh enabled that organization is the organization you just talked about to change since it couldn't be you per se?

Hugo Gatsby:
That's a great question and and I'll I'll start it with that first year I was in military school I went to the Royal Military College when I was 14. and it was it was it was grueling and I thought I was I literally thought I was going to die I guess I just couldn't get through it and I got through it but at the end the officer came up to my stepdad my mom's wife at the time but said you have a really amazing son here he's like I know he's like no I I think you need to like you really and seeing the look in his eye like he wasn't he didn't see anything that I did but he had that sense of pride in him and I think that moment to me made me so emotional but it also made me realize that when you're a leader people don't need to see you to feel your your impact feel your impression.
So when you're talking about scale, I think you need to understand what is going to make people feel both challenged and safe simultaneously. Effective leadership techniques play a big role here, as they help leaders balance these elements while encouraging growth. Everyone, understandably, has financial concerns, especially with recessions and economic uncertainty. But I believe money should not be the only motivator. From my own experience, I can say that making more money doesn’t necessarily bring more happiness. So as a leader, you have to look beyond finances and focus on communication in leadership to build trust and ensure each person’s motivations align with the team’s goals.

The key to cultivating high-performing teams lies in understanding what drives each team member. Some people seek achievement or thrive on challenges, while others value security or recognition. To scale effectively, it’s essential to connect with individuals, understanding what motivates them and how they best receive feedback. That’s where team empowerment strategies come into play, allowing people to take ownership and feel valued. Behavioral science and behavioral finance have taught me the importance of addressing biases and adjusting communication styles to better connect with others.

In any leadership position, it’s a choose your own adventure methodology, adapting based on what works best for each person and the team. I haven’t yet led a team of 500 people, but accountability in leadership is something I consider vital for scaling effectively. Building a team where each person feels supported, heard, and accountable is, I think, the foundation of any sustainable and successful organization.
But it pops into pads like how will I be able to create a culture that is sustainable and I think that's where the idea comes into play like inclusion diversity equity and accessibility like all those elements need to tie together because everybody is amazing and creative and wonderful and in their own right you need to find what their potential is and help them see that potential in themselves and when you do it's it's going to change something for the better and you just need to figure out how to evolve with that it's there's a person a really bad business partner had actually but it gave me really great advice at one point but his goal was when he's building his brand or his company his idea he can either have a person who's going to challenge it and grow and leave that organization or he can grow their organization to fit that idea as well so they always stay together and they always grow.
And that kind of reminded me of my military days where it was like in you know uh inspire people to stay and you're growing your purpose your idea to include what they want to do because you're invested in them and if you could find a way of doing that um with a lot of people which sounds like it's hard but it really isn't because everyone has a purpose and a reason just got to figure out how to get them to communicate that how to get them to trust you and that trust and relationship is really important so I've I've ways that I would do it but I haven't come to that state in my life yet probably in the next five years I'd say maybe but until then I'm just just hustling like everybody else.

Host:
Well I think you have a good start or a good Baseline I think this idea of safety and challenge is really important because I think, you know, it's actually just sort of... I'm going to make an assumption here, even just how children, like, you know, feel or grow in general. You make them safe, but you have to challenge them. And if you can create... and it's very tough to create that in a business environment for all kinds of reasons, but if you can't create it, I mean, that is the baseline with which anybody can grow. And I think, you know, good luck on the journey of making that happen with sort of how you're doing things. But I think those axioms are hard to make happen. If you can make them happen, it's hard for people to think. So, I think that's a great thing I took from then, and I think it's really valuable.

I think I even had an experience once with a much younger engineer—very, very smart, very smart—and there were some wheels that allowed him to reinvent just because it allowed him to feel creative. And he made some really cool things, and, you know, it created the baseline for some other things that we were able to leverage within that project. And I think that safety... I didn't want to kill that spark of creativity he had. I didn’t want to say, "Oh, there's something else that exists already." He was able to deliver that thing even though we had it before and gave him that confidence to continue to do it. Sort of trading off, like, okay, here's your piece, here's our piece, here's your piece, here's our piece. I mean, honestly, when other people saw what was made, they were like, "This is quite some engineering you've done here." So, I really resonate with that idea of feeling safe, feeling secure in where you are and what someone is creating for you, that space, but also feeling challenged. Like, okay, you do have to deliver here, though. But we are all on your side.

So, one of the questions I have here, you've alluded to a little bit, is: what is a behavioral strategist? It sounds very airy-fairy, but I think, with all the things you've talked about already, it has quite a bit of substance to it.

Hugo Gatsby:
Yeah, no, great question. So, a behavioral strategist works on the concepts of what we call cognitive bias. So, you make tens of thousands of decisions a day—95% of them are automated, so you don't even think about them. And that's where those biases come in. About 5% of what you think about are action decisions, decisions you actively make. So, one of the roles we have is, if decisions are made kind of by the hip and instantaneously, how do we influence that for people to make better decisions? And it’s not brainwashing, telling them to make a decision this way, but it’s showing them kind of an architecture so they think about the decision, make a more educated decision, and ultimately make better decisions.

A great example is when I was working with the Bank of Montreal. I actually brought Behavioral Science into their organization and helped implement it into their digital adoption strategy—so, people going onto mobile banking. A lot of people, you know, in their mid-to-late 50s, were the median customer there. How do you get those people to want to use digital banking instead of going into the bank? We went through a series of tests, research, and experiments to see what was working and different ways of incentivizing them. We gamified it, and gamification has a lot of elements from Behavioral Science, a lot of biases. We tried to figure out what some of those major blockers were and how to overcome them or circumvent them to get the decision to be made faster, more efficiently, and proactively, to be more beneficial to that individual.

A lot of those 401(k) plans you see, or when organizations offer things like matching for RRSP contributions—that’s all Behavioral Science at play. Those are really great examples of how you're making their lives better. Now, they won’t see it immediately, but 10, 15, 20 years down the road, when they’re retiring, they’ll think, “Wow, where did I make all this money?” It’s because this company used Behavioral Science on you to influence you.

There’s also levels of motivation, and there are different theories of thought, so I don’t want to go into what I prescribe to, but it adapts depending on the situation. I like the concept of intrinsic and extrinsic motivation, and how those influences will impact either individuals or groups of organizations. Those pieces then help you filter down to what biases are prevalent in those types of people.

Host:
So, are there stark differences between those? You talk about intrinsic and extrinsic—are there stark differences between those? But more importantly, what's interesting to me is: are there motivations that groups have that individuals don’t, or vice versa? Is that stark enough? That's interesting.

Hugo Gatsby:
Yeah, 100%. So, there are always outliers. I think effective leadership techniques are crucial in understanding what drives people, especially when managing diverse groups with different motivators. Intrinsic motivators, like a sense of purpose and belonging, play a big role, but communication in leadership is essential to align those internal drivers with organizational goals. For instance, extrinsic motivators can reinforce that sense of belonging and recognition, which often matters as much as monetary rewards.

In consulting, cultivating high-performing teams means recognizing that some people are motivated by prestige, while others want security or challenge. Team empowerment strategies can bring out the best in everyone, allowing people to contribute effectively to high-stakes projects. Within consulting firms, the motivation isn’t just salary-focused; it's about the excitement of tackling difficult, unsolved problems. For example, some consultants thrive on the challenge of problem-solving because it brings a sense of achievement and fulfillment.

The '80s emphasized a “win at all costs” mentality in consulting and investment banking, but there’s now a shift toward accountability in leadership and sustainable, people-centered practices. Deloitte, for instance, has embraced this change, building a culture that values the professional growth and well-being of its people. I have met many colleagues there whom I consider mentors and friends, people who I would keep in touch with regardless of where my career takes me.

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Host: 

So you talked a lot about the behavioral strategy, and you talked about the motivators, right? So people are motivated by different things, not necessarily always sort of compensation-based. It's not always about money, right? So to me, I was thinking, okay, so the ones that weren't based on money, the most stark place to apply those would be a military school. Because the expectations are high, right? But there is no compensation, especially in a military school. There's literally no compensation where that has to do with money. But they are able to motivate people to quite a degree, even for yourself, even though you felt like you had a few challenges here and there. So, you know, if you were able to apply what you've learned so far to how military school is able to affect you positively, what would those things have been?

Hugo Gatsby: 

To know that I couldn't do something and then to see, you know, two months later that I was able to do it shows me a sense of perseverance and determination. And I think, you know, perseverance—like, I could probably outstare a mountain with like my determination. And then I think my wife could tell you, like, sometimes I will say something and she'll think it's like just a half-assed joke. And then she'll realize it, it's fruition. I'm like, I said this to you, and she's like, I thought you were being sarcastic. I am not sarcastic. I understand this, but this is also something that would never actually really happen in real life. And I think that military school taught me that. You know, I try to be as honest as possible, and when I say something, I say it to put it out in the universe, and when I say it, I know that I will do it because I'm not, I don't want to let myself down. I've been let down by a lot of people in my life, so I don't want to be that person to others. I don't want to be that person to myself. And I want my kids, you know, to see that and say, you know, our dad said what he was going to do and did everything he could to make everybody's lives better, not just our own. And I want to make sure that, and those are things that I saw in military school. You know, you don't get, you can't do it by yourself. You can't be successful by yourself. You need to have somebody, something.

And I think that is the part of camaraderie that I appreciate. There’s a handful of people that I talk to on a weekly basis, and, you know, we work together, we do things together, we have projects together. Everything from building an industry that doesn’t exist to buying a castle—these are all the conversations I have with people. And full-length, like, not just, “Oh, let’s do this to be fun,” but more like, “No, here’s a 15-year strategy. Here’s a 15-year plan.” It keeps us engaged and looking toward the same goal. If that goal changes, totally fine, but it’s a conversation we have together and not a conversation you have by yourself.

To achieve these ambitions, I’ve found that effective leadership techniques and team empowerment strategies are crucial. Knowing how to create the right environment for cultivating high-performing teams has a huge impact on team dynamics and overall success. I also believe that strong communication in leadership is essential, especially in fostering trust and clarity as we work toward common goals.

Solitude can be valuable for creativity, understanding, and reflection, but there’s a sense of relationship that you need in everybody’s life. In my late 20s and early 30s, I went through some darker years, and I really wish I had been more open to people. After some of those experiences, I started to talk about my autism openly and understand who I was. That’s when my life took off; the version of me from 35 to 40 was entirely different from my 20s.

These experiences taught me that accountability in leadership plays a significant role. These leadership strategies have been key in keeping me grounded, helping me stay focused, and keeping others motivated as we push toward common goals. It’s not just about personal growth—it's about helping others see the possibilities in themselves. That’s what leadership strategies are truly about: encouraging others to find their purpose and elevate their potential. These values of determination and mutual support play out in both professional settings and personal endeavors, whether it’s building something new or simply moving forward together.

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Host: Well, if someone was determined to find you, either for camaraderie, for productivity, or uh, to reach a goal, where would they be able to do that?

Hugo Gatsby: I mean, I have so many sites that I run. I would say reach out to them, reach out to me on LinkedIn. Um, I think LinkedIn is the best place. I get—I get a lot of messages every week, but a lot of them are just, you know, buy my thing off me, buy my thing off me, and I've had, you know, maybe a half dozen people a year that reach out to me genuinely, and all those people I still talk to, and all those people are really amazing. And if you want to reach out to me, talk to me, we can work together, we can just have a chat, you know, that's the best place to do it, to get in touch with me, and then from there, we can figure out where we go. I think it's always an adventure, so yeah, Choose Your Own Adventure at that point.

Host: Thank you so much.

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