CTO Wisdom with Barnaby Dorfman | Beyond the Program

Tim Winkler: 00:00:00

Hey, listeners, Tim Winkler here, your host of The Pair Program. We've got exciting news introducing our latest partner series Beyond the Program. In these special episodes, we're passing the mic to some of our savvy former guests who are returning as guest hosts, get ready for unfiltered conversations, exclusive insights, and unexpected twist as our alumni pair up with their chosen guest. Each guest host is a trailblazing expert in a unique technical field. Think data, product management, and engineering, all with a keen focus on startups and career growth. Look out for these bonus episodes dropping every other week, bridging the gaps between our traditional pair program episodes. So buckle up and get ready to venture Beyond the Program. Enjoy.

Eric Brooke: 00:00:53

Welcome to CTO Wisdom. My name is Eric Brooke. This series will talk to leaders of technology at organizations. We'll understand their career, what was successful and what was not and what they learned along the way. We'll also look at what the tech market is doing today. We'll understand where they gather their intelligence so they can grow and scale with their organizations. Hey, Barnaby, welcome to CTO wisdom.

Barnaby Dorfman: 00:01:28

Hi,

Eric Brooke: 00:01:28

great to be here. Um, could you give me the elevator pitch of yourself, please?

Barnaby Dorfman: 00:01:34

Sure. I am a serial chief product and technology officer. Been doing it for 25, 30 years. Um, grew up, sort of cut my teeth in early Amazon, worked on, uh, everything from the first version of the Amazon marketplace to, to core search technology, uh, recommendations, personalization, and a few things in the middle. And then. Since then, I've spent just decades in early stage startups and then more recently kind of, um, scale ups. So kind of going from 10, 20 million annual recurring revenue up into north of a hundred million. A lot of that in the HR space, HR information, human resources, uh, but a lot of experience with media as well, and really take an integrative approach between, uh, product design engineering Uh, and then also just as a C suite executive, kind of the connection between the tech org and the rest of the company is something that I've really been leaning into in the latter years. Awesome.

Eric Brooke: 00:02:33

Could you tell us about your journey to becoming an exec? So maybe go back to when you're a manager, you choose which point you want to do. Um, what was that like? And what did you learn about at that point of your career?

Barnaby Dorfman: 00:02:46

Sure. I mean, it's, it's a constant evolution and in some ways be hard to pick a single point, but I guess I would say. I would, I would pick a couple of things. One, I went to business school, I have an MBA, and I think that really creates a lot of the foundation for what you need. Uh, you know, people ask me frequently today if they still think it's relevant. And I use things that I learned in business school from decades ago on a daily basis. Um, so I think that's a foundational piece. Uh, but you know, I think again, back to my time. At, at, uh, I want, you know, I went up at Amazon as part of an acquisition. I was essentially in the C suite of a small startup that then went up at Amazon, but Amazon was very small. And I mean, I think there were maybe 200 people in corporate in Seattle at the time, most, if not the whole time I was there about seven years, my managers reported to Jeff Bezos. So while I wasn't in the C suite as a C level executive, I was physically present. So I kind of in the room where it happens, if you will. Um, and I got to see. You know, incredibly smart people figuring it out as they went, because they were also junior and doing it for the first time, um, and in some ways kind of catch up to the industry and in some ways go beyond and invent new things, you know, like some of the things that are pretty famous about Amazon today, you know, it was amazing to watch them unfold and unfurl. Um, that's, that's, that was kind of a step function that I would say if I jumped forward, you know, was it a number of smaller startups, um, where the difference between being an individual contributor and, and, uh, you know, in a C level executive was not that great. Um, but then when I got into kind of, again, the scale ups where we went from tens or a hundred people to hundreds of people and tens or sub 10 million in revenue to over a hundred million, that's where I really learned. kind of what it takes to be that connective tissue that, you know, becoming a, you know, a C level executive requires.

Eric Brooke: 00:04:39

Okay. So when you think about, um, your management journey, what are some of the powerful things before you got to C suite that you learned along the way?

Barnaby Dorfman: 00:04:50

You know, I think a lot of it was around pitching my ideas. You know, one of the things I love about software development is everything's possible. You know, the, the feasible region, if you will, of what can be done is essentially infinite. But the problem with that is that, you know, it's, if you're talking about, Oh, I want to build a bridge or I want to build a building, you know, it's kind of the, the set of things that are possible is much more limited by physics. And, you know, History of architecture, things like that. But, uh, tech is so unlimited. And so one of the things I struggled with early on was having these ideas and communicating them and basically selling my ideas, selling myself and my ideas. And frankly, I think showing up in a way that was, you know, emotionally intelligent and. You know, I think early on, even though I was right about some things that turned out to be absolutely massive monster businesses over time, I did not present that in a way in a way that helped other people understand, sort it relative to all the other great ideas, because the whole thing is just exploding in the early web. Um, so that, that was a, that's a kind of a really important piece. Uh, you know, I mean, an example of that would be again, the Amazon marketplace, which was very controversial internally. And. Yeah, you can understand why you have an established business selling books and suddenly you want third parties to sell books and treat your customers as well as you would and not mess up your relationship with publishers. Um, But the way that we were going about it, frankly, wasn't working because we had them separate and, um, and again, I, I just got frustrated and I just like expected people to see things the way I saw them. And it was, it's really been kind of in growing and learning that, Hey, everybody's doing their best, you know, almost all the time. All people are trying to do their best work and the best thing for less themselves, but their, their company, their team. Um, and if you can. Find ways of relating to them and figuring out where their objections and they may just be right. It's the other thing you may be wrong. Your idea may not work, but I guess the thumb it's really around being better at, um, also just using metrics and analytics to present in a very objective way and then really getting into the shoes of the person that I need to get buy in from, um, rather than just sort of wanting to shake them and say, can't you see it?

Eric Brooke: 00:07:12

So, yeah, what I heard was like, you went from here's the idea and people would, you get a resounding silence to what are the people I'm trying to convince, who are they, what do they want, what do they need, what convinces them, whether it be metrics and improving that influencing capability.

Barnaby Dorfman: 00:07:31

Absolutely. Yeah. Good summary. Cool.

Eric Brooke: 00:07:34

Okay. So you've been, you've kind of like building up this skill set, you're becoming a manager and then you eventually get to managing of managers. Do you have any thoughts or recommendations for people that are like getting to manage managers for the first time?

Barnaby Dorfman: 00:07:50

That's a good question. People usually ask me about managing for the first time, but managing managers, I think, I think it really is, you know, you have to think you have to lead through more layers of abstraction, right? Like, you, you can't, you can't influence people directly, especially as the org gets larger. If you're managing hundreds of, you know, have an organization with hundreds of people and managers and managers reporting into you. The, the ability to kind of stand next to somebody and help them through a problem or, you know, work with them directly basically goes away. There's just not enough time in the day or the week. Um, so you really have to think about how you can simplify. Even more, I mean, simplification is always important, but I think that again, if I can stand there face to face and explain my half baked idea and, you know, and how do you ask questions till we get there? That's 1 way of working with somebody as a manager or the inverse there and perfect ideas and you're helping them get get it fully baked. But once you get into the managing managers, I think that's the best way to go. Now communication becomes harder and something you have to be much more thoughtful about and put more effort into. I like to say that the transparency, which I believe is super important, is not the opposite of keeping secrets. Transparency, you know, requires effort. You have to work at it. You have to craft the message. You have to think about the delivery mechanism, the timing, the audience. All of these things become much, much more important. Everything around communication becomes a much bigger issue. I think one of the advantages that, um, people should lean into is now you actually have a portfolio. You're, you're essentially working with a portfolio of talent versus, you know, a toolbox of talent. You know, I think, and if you think about kind of investment theory, that diversification is, You know, almost always a benefit, you know, in the stock portfolio, same thing with, with a talent portfolio and how you think about how you balance that and you think about the, um, the makeup of that talent pool and how well it meets the needs of your organization, the strategy, the various stakeholders, there's, you know, there's kind of this, um, much more. Zoomed out view that you have to take and think about sort of how the pieces all fit together. Uh, and it'd be planning, you know, thoughtful about that. I think, you know, one of for as an example Having a strategy for hiring, you know, i've scaled Engineering product tech teams from single digits, you know, into triple digits or, you know, very fast growth at times. And, you know, we're depending on where we are in the cycle. And I've made some terrible mistakes. Like, 1 of the ones that I've really been leaning into, you know, now for quite some time is just, um, thinking hard about the ratio of senior to junior. And at one company where we got a funding round and, you know, we're expected to grow the team and do some acquisitions and some integrations and just tons of growth. Um, I was strongly encouraged by a variety of, uh, stakeholders that I should hire a bunch of senior. Particularly in engineering. And so I did that and they all wanted the title of architect. So I had, you know, I had a friend of an architect and a backend architect and a mid tier architect and a lunch architect and like everybody was an architect and, you know, and then eventually they just, they, they, they all thought, you know, like cats in a bag. I mean, it was, it was not a good situation because. So often with technology, there isn't a right architecture, more important than anything. It's everybody's agreed on and following the patterns that, you know, have been set forth. And if you've got three or four or five people who believe it's their job to define those patterns, you wind up in a really bad place. And so I think, um, being very thoughtful about that ratio of junior to senior. Uh, and always role clarity is super important. It's important at all levels. But again, if you've got a larger organization having good clean lines of separation of who owns what, where, where's, where is the separation between two orgs or two teams, because if there's a lot of overlap, you wind up with a lot of Problems. And if there's no overlap, you wind up with a lot of problems. So you want, you know, kind of, you want them sort of adjacent or, or touching shoulders, but not, um, you know, trying to sit in the same chair.

Eric Brooke: 00:12:19

So you talked about the ratio of, like, over employing in terms of senior, and that having a lot of architects. So what do you actually use as a basis now? Because obviously, the implicit of what you're saying is that you should hire juniors as well as seniors. How do you think about that now?

Barnaby Dorfman: 00:12:40

It really depends on what you're building, where you are in kind of the lifecycle of the technology, the company. So if you're, you know, if you're earlier stage or you're building completely new stuff, um, you know, that you're going to need to start with some senior people who can design an architect. If you're just maintaining something, you probably don't need an architect. You know, and there are everybody always in this business wants to, you know, kind of be moving quickly and changing and replacing. And sometimes it's just not the right thing for the business or in the marketplace. Um, so if something is in maintenance mode, uh, or, you know, some other kind of. Mode, say lots of integrations and connections with third parties is another thing that I've experienced. You, again, you don't really need to be building stuff, whole cloth and you don't need architects, but also if you've got a lot of serious tech debt and or, um, a need to evolve a product because of some technical innovation, I mean, artificial intelligence, large language models, where, you know, Huge right now, and they are going to impact a lot of business and businesses, and they are going to require reworking and refactoring many, many, many applications. So those are some examples of places where, again, I think you'd lean into some, some more senior folks. I will say also, you know, there are a number of, for a number of reasons, I believe that more junior people are more capable than they ever have been, and it's not, that's not a slight against more senior people and their unique abilities. But I think the. The change, there's a few things that have happened. One, the knowledge base that's available online, you know, not in books, you know, those, remember those big, thick Q books that, you know, we were expected to read, to learn how to use Excel. Yeah. Right behind you. It's sound installation now. Right. Um, and, um, and so that's all available online. And now also with, you know, like a chat GPT, you can actually. Sort of interrogate that knowledge base in ways you never could before. So that's what's available from a knowledge perspective has really come a long ways and continues to, to, to accelerate. Then I would say also the tool set, right? Like the number of, um, I mean, low code, no code cloud, you know, when a, when a new software development engineer sits down at their desk for the first time, they are empowered with a master, skill level set of tools on day one. Um, and that's also a change. And I think within that is also some architectural processes things. So, you know, continuous employment, continuous, um, you know, CICD, continuous integration, continuous deployment, um, is something, and, and, and then also kind of like the ability to launch things, Uh, you know, into a branch, um, on production, but, um, you know, behind a feature flag so that it's internal users, only testers, and then do a canary release where the, you know, the number of external users ramps from 0 to 1, you know, not up to 100 percent means that. Whereas, say, 20 years ago, a new grad out of software, uh, out of a software development engineering program, computer science program, might be expected to spend months learning, you know, the architecture and, uh, custom tools and language modifications and, and the business before they check in any code that goes to production. Also, the development and deployment cycles were much longer. Now, you know, I, I believe in a lot of companies like, like Meta, I think, you know, you're expected to check in code to production on day one. Um, and so all of that means that I think you can, if you're thinking about that portfolio of talent I mentioned, um, you can get a lot more done with more junior people than you used to. The ratios of like sort of straight out of school, you know, Uh, 1 to say, you know, 3 or 5 years, 5 to 8 or 10, you know, 10 to 15 and then more senior. I think the, um, you know, you can get a lot more done with more people at the junior end than you could before.

Eric Brooke: 00:16:46

Yeah. And to add to that, and I think you included this, there's so much better tooling that we don't have so much complexity that we used to have. Um, And we don't need to create everything custom, right? Okay. So, um, managing managers, you talked about transparency. You talked about getting the right, um, ratio of junior and seniors considering the context of the business and what the business needs heard that all. Um, what else would you say is important for helping managers? Um, managing managers?

Barnaby Dorfman: 00:17:21

I think it's the, your role as connective tissue to other parts of your organization. And I, you know, I tend to think of these things as con concentric circles, right? So one of the ways that I've des sort of describe career progression to, to people, especially young people outta school, is it's little bit like dropping a upon a pebble in a pond. You're the pebble and when the pebble first drops, you know, there's that one little circle and that's, that's your first year, you know, out of school and then over time, those rings go out and out and out and by the time you're, you know, you're at the C suite, you've reached the edges of the pond, all edges, right? Like, you're touching everything, your wrinkles and your, your, the energy that you put out reaches the whole organization. So. As you're in that, that journey, think about kind of where you are. And so let's say you're a new manager of managers. Um, you've got one, you know, one sort of skip level below the, your direct reports. Um, and you're one of say five direct reports to You know, a VP or a C level executive, or, you know, sort of senior director. Um, you know, you need to really think about how you help your teams. Um, assuming that each manager you manage represents an individual team, how are they connecting with each other? What, you know, what mechanisms have you created for them to be. Aligned, um, have transparency with each other, uh, you know, hold each other accountable, celebrate each other's successes, all of those things, then, and that's kind of your oversight within the, your group of people that you manage, then there's, okay, now I, as a manager of, you know, as a senior manager or maybe a director level, um, how do I effectively connect with. My peers within, you know, the, the, all the people that report to the, my manager, so that's, and that's, I really liked the idea of the first team. Um, the author, Patrick Munchione, uh, kind of, I think he introduced it. That's where I learned it. It's the notion that your first team is not the people who report to you or the, in this case, the managers that you manage, but it's actually the people. Your peers who report into your manager and you're accountable, you know, that your success is dependent on their success and vice versa. And so making sure that you have, you know, really good collegial, hopefully friendship level relationships with those folks, because that the alignment or lack thereof is what's going to determine. The success of, you know, your immediate organization and your manager's success, the organization, you know, that success. And then I think you start thinking about, um, you know, okay, where else in the organization do I need to be connecting? So, you know, I think like relationships between tech org and, um, product marketing sales. support, sometimes legal, um, are kind of notoriously not great. And I think that one of the things that as people start to move up, they can have a very positive impact on, but they can also learn for themselves is how do I effectively in a positive way with as much emotional intelligence as I can engage with those other functions? So that, you know, let's say legal, for example, you're going through GDPR issues or, you know, other, uh, maybe, you know, contractual kinds of things. IT and security can be another area of either friction or wonderful collaboration. Um, but like. Building a relationship, understanding, you know, why the legal department has created, you know, whatever structures that has, you know, why they think it's important that I do or not do these things, um, and, and just really show up and be present to understand. Kind of things from their perspective on the support side. I think that's an area that, uh, you know, if you don't have a good relationship with the support org, you're not going to have quality software in my experience. Like they're, they're the tip of the spear of where, um, so many of the quality problems that are, that our users, our customers are experiencing, um, comes in contact. And if we think about. For yourself, like how upset and angry and frustrated you have to be before you file a ticket, right? Like, you'll like, most of us just because it's so painful for so many organizations. So, by the time somebody's actually filed the ticket, um. You know, they've already gotten to a level of, of, you know, frustration and if the support org is saying, and I'm getting a lot of these, or I'm, I'm having to do these workarounds to help our customers or whatever, I think it's really important to really listen to that and, and be extremely empathetic and try everything you can to fully understand what the issue is. And not fall into the temptation of, oh, you know, people just don't understand or don't know how to use it or whatever it is, or you need to do a better job of explaining it and just think about how can you incorporate that into. Your daily work, monthly work, you know, your planning, et cetera. And again, finding that, that balance, because one of the back to the point about in software, the possibilities are endless. So are the demands, right? Like, and so you leveraging, and I think, well, I don't think I know software development, engineers, programmers, they like building high quality software, they don't like bugs. And one of, you know, you can, you can, I've seen relationships go from. Oh, we just, you know, the support org just doesn't get it to, Oh, the support org gives me the data that I need to be able to then go work with my product managers, my, you know, business, um, you know, stakeholders, whoever it is and say, Hey, I know that you think that feature would be really cool. Um, but we've got a, you know, a large number of users who are actually trying to use this feature we built that they want, and they, you know, Like, but it doesn't work correctly because there is a bug or there's an exception or whatever it is. I'm going to put time and resources into fixing this or making this better before I build that new thing that you're excited about. And, you know, there's a lot you can talk about how to manage that, but. Um, there's an interplay, I guess is what I'm trying to say between the, the interactions and the, the data and anecdotes that you get back from other organizations. And I just chose support as one to focus on. But sales is another mar marketing product. Marketing is another finance, uh, you know, living in your budget. That, that's another one that I think is like just deer in headlights for a lot of first time managers. Managers in particular where now you're actually allocating. Things like dollars between, you know, teams and people in, in a much more, um, expansive and dynamic way. Uh, and so, you know, your partnership with, with finance can become a really important part of, of your role.

Eric Brooke: 00:24:36

So setting up a community for your peers is an important thing. So you can learn from each other, give each other feedback, um, and also expanding beyond technology into the other departments to understand. One, what are they doing? Why are they doing it? Building empathy for them. And then also building stronger relationships is the kind of things. And customer success is like, obviously the one that you primarily use. And I 100 percent agree with you. They are the best bug hunters because your consumers are finding things. So that's great. So, and also the first team mentality. So moving to the, your first team moves. So you're now in the exec. How, what was that transition like for you, if you can remember it and what are the important things to think about when you're in the VP role before you've got to the CTO role?

Barnaby Dorfman: 00:25:27

Yeah, I, I, a bunch of failures. You know, uh, ranging from just, again, not doing a good job of building bridges. And, you know, I, I, there's a thing that happens a lot in tech, which is that tech tech builds up technology moves on. And I think the human instinct is you sort of out with the old and with the new and like, let's, let's, you know, let's just bring cleaning and we're going to do, you know, we're going to go from V1 to V2 and that also used to be how software was built right when we had to put, put it on to disk and mail it out to people you had multi year development cycles because you. You know, you couldn't test, you didn't know what people were doing or how they were using it, and you couldn't fix bugs, uh, you know, once they went out, so you just really had to go, you know, slow and steady. The web is just not like that. Um, but the, I think kind of this, this notion that it's time to just rip and replace is something that I've, I've embraced and failed at several times. I've resisted and failed in being effective at communicating the why and. So, I think that, I'm thinking about it as an example of places where I had conflict or lack of alignment with other people within, you know, or other VPs, um, and, you know, either didn't succeed in what I was doing or caused general failure to spread. Um, and, and it really just, again, comes down to relationships. I think, um, Yeah, just being really, really thoughtful about my interpersonal relationships and, you know, in some ways I'm repeating kind of what it was as I went from, but it just, it just gets more important as you go. And, uh, I'm trying to think of other things that sort of definitively change. Well, your time horizons change a lot. I guess that's something I didn't I haven't mentioned yet. I think that, you know, you tend to. You're an individual contributor. You know, you're, you're heads down focused on what I'm doing today. And, you know, kind of what's expected of me, you know, the sprint, um, you know, and I'm probably curious about the company strategy, you know, what's going on and stuff, but, you know, I don't really pay that much attention unless there's a really healthy, well developed OKR quarterly kind of system. But most of my day to day is like focused on the here and now, and then as you move up, you know, you maybe you're, you're thinking, you know, you're, you're responsible for if you're, if you've really leaned into agile, uh, two experience, you know, you're, you're sort of, that's, you know, like the last sprint and, and sort of this sprint, and maybe you're thinking about next sprint. Right. So that's kind of a six week spread, if you will. Um, yeah. I think that, you know, then once you become kind of a VP level, you tend to think about like quarterly OKRs, quarterly QBRs, quarterly business reviews, um, and then, you know, once you get into the, to the C suite, um, or, or kind of go further, then now you tend to think about, you know, there's an annual planning cycle that you spend months on, um, there's, you know, kind of mid year review and, you know, there's an annual, um, Planning, um, budgeting, you know, the budget planning becomes that frame that you work inside of, um, and then you also tend to worry about things, you know, at a strategic level out, you know, 3 5 years, um, hopefully you're in an organization that does that kind of thoughtful stuff. At least every couple of years is kind of, you know, I think people tend to work with a strategy too often. Uh, don't give enough time to execute, which tends to lead to a little too much, um, context switching. Uh, but a thoughtful balance of really long term, you know, where is this company going to be? You know, in 20 years, um, if, if, you know, if that's, if that's an appropriate frame, it doesn't always, but you know, somebody like that was something that I definitely learned from Jeff Bezos, you know, and he's pretty famous slash infamous for that long term thinking. Um, but. Yeah, those time horizons expand. And in that time you spend thinking about working on, um, producing work product, you know, analytics, frameworks, documents, presentations, um, that spreads over a longer period. And it's more forward looking, uh, is a big, big piece of it. I think also, Yeah. Metrics, you know, if you're just if you're building software, you maybe you're maybe you're responsible for, you know, some dashboards and monitoring services or those kinds of things. But typically, you're, you're not looking at a larger, broader dashboard and the connectivity again between, um. You know, unit sales or, or, um, subscriptions and things like churn and average revenue per user and, uh, customer acquisition costs and, uh, hosting costs, the cost of goods, you know, everything that goes into cost of goods sold. Cost of, of, uh, headcount, the biggest, you know, the biggest chunk of all the budgets that I've managed, you know, in C, CPCTO roles. Um, you know, and then again, the connectivity that to profitability and then typically, you know, whether it's a startup or a PE backed company, and I've been in both. You do have some sort of a horizon, you know, uh, uh, event, an exit, a sale that you're thinking about. And, and you may be actively working on that, or you just may be like, we just got acquired by a PE. And so we know their average hold period is four or five years. So, you know, they're going to come in and there's going to be an immediate action plan. And then there's going to be a series of years of execution. And then we're going to get it ready for sale where you are in that cycle. But again, these longer time horizons, there's a few examples of how that can work that I think becomes part of your day to day as you get more senior.

Eric Brooke: 00:31:42

So, when you think about it, Barnaby, what does success look like for you? And what has helped you be successful?

Barnaby Dorfman: 00:31:51

You know, I think for me, uh, you know, I mean, I'm not economically rational, rational. I'm economically rational, so I care about money. Um, but You know, i've also realized that If you spend a lot of time thinking about it or worrying about it, you're probably not actually going to be successful in making a lot of money. And most, most of the really wealthy people that I know don't spend a whole lot of time thinking about, you know, what it takes to make money or how they made the money or how to make more money. Um, they think about how to create value in the world. And so for me, you know, whereas money and title maybe were more important to me now, it's really, am I creating value? Um, and am I creating value on probably two primary vectors? One is it just for customers in the world, I'm highly customer centric. And so am I building, improving, creating, maintaining, whatever it is, a product solution that large numbers of people. You know, find valuable impacts their lives in positive ways, reduces some pain somehow, um, makes things easier for them, helps them cut costs or be more successful. The other vector is how well am I doing internally in terms of, um, having, You know, happy, healthy employees who are in themselves being successful in whatever, however, they define it, whatever their goals are, their growth, um, you know, the fundamentals of the Maslow's hierarchy stuff of, can I feed myself and take care of my family? Um, and then, you know, up into self actualization of like, you know, that classic thing that a lot of engineers hit, which I really love coding, but I've been at it for, you know, 12 years and I'm getting asked to, you know, manage a team and I'm not sure if I want to, and how can I, you know, and, and, and so I'm at that fork in the road and, um, you know, how can I help them through that? Uh, which can be, you know, scary and lead to people leaving companies because of, you know, that can be handled poorly, or it can lead to, you know, I've had, you know, I've seen people step into leadership who were kind of resistant to it and didn't think it was for them and they've blossomed and been incredibly successful at it. I've seen people who you would think because of their personality, you know, they seem, you know, sort of outgoing, gregarious, whatever. Turns out, no, you know what their best uses is, you know, Sitting at a keyboard most of the day. Um, coding. Uh, and I've seen, I've seen hybrids and I've seen people, but I've, I've also seen people leave companies because of how that transition was handled or how the need to go back the other direction was handled. Uh, so that's a little bit of a deep dive into my definition of success is, is really the success of my, Organization and, and, and, and again, like I said earlier, not just the people in the report up in the mirror in my, in my immediate, um, team, but also, you know, if, if engineering is doing great, but sales can't sell anything, or they're not hitting their quotas. It doesn't, you know, it doesn't work. So it's, it's how, how well is the collective doing and what's helped you be

Eric Brooke: 00:35:12

successful?

Barnaby Dorfman: 00:35:15

Well, I would say mistakes and failure and learning from them that, you know, that's always really, really important. I think curiosity, just be curious. And if you don't know the answer to something, maybe also being a little bit impatient to get an answer. And sometimes that's just a Google search, but sometimes there is no answer. Nobody's ever thought of the question. Um, because nobody's been in the situation you're in, uh, having been, you know, Working in internet powered technologies since a really long time, the, uh, in my life, but a very short period and, you know, in the span of human history, um, there's just, uh, you know, I've been lucky to be on, you know, kind of out of the front of the frontier of so many things. And so, so often. There is no answer. The only way to get an answer is to do an experiment and explore and try, try new things that nobody's ever done before. Um, so I think back to the question of what makes me successful is I seek that out. You know, if somebody tells me, Hey, go do this. And I'm like, that's, that's a solved problem. Like, you know, There are lots and lots of people who've done that probably done it better than me. I'm not going to gravitate towards that. I'm going to gravitate more towards the thing that is like, nobody's ever done it probably isn't going to work, but if it does, you know, you can change the world. Um, and that's part of that curiosity thing. Um, I think a few other things that come to mind are really, really focusing on, on sort of the human side of things. I just, I think a lot of engineers. Consider themselves to be highly analytical and that they make decisions based on data and facts. They also tend to be more introverted than extroverted sort of on the spectrum on on that spectrum. They tend to, you know, sort of turn towards that side. And what I, what I've seen is that that can lead to somebody who thinks that they are a non emotional creature, um, And, and then they sort of deny their feelings about a thing about, Hey, that reorg was the fifth this year, and I don't even understand why I'm building what I'm building, or, you know, they just, they just promoted this guy's been sitting next to me for two months, you know, just joined the company two months ago, and I've been here for two years and I have more experience and I don't understand it. And, you know, whatever it is. And, and I think as a result, they can often bottle up some, some of the emotions and feelings about, um, how things are going and then, and then it can explode in a, in a nonproductive way. So, you know, being really, really thoughtful about the people. And I think, listen, I have this sort of working hypothesis right now that, um, we've, we've. As an industry created so many of the building blocks, foundational technologies, ways of working, uh, infrastructure, you know, we, we can rely on high speed, you know, ubiquitously available bandwidth pretty much anywhere on the planet. Now, um, we don't have to buy expensive software to build software, the open source, you know, operating systems and frameworks, you know, cloud computer. We don't have to, I have to rack them. Hardware have people get up in the middle of the night to switch out hard drives. I mean, I can keep going, I think, you know, mobile and now the gen AI is kind of that next step function of, of building blocks and yet based on, you know, despite all of that, most, most applications, most web applications, mobile applications are mediocre at best. And, and there's some good ones that drag up the average, you know, sort of mainly the big tech companies, not that they don't still have their usability problems, but you get to the average, um, bank, airline, government, school, hospital website, and it can be almost impossible to get basic stuff done. Uh, and why is that? Well, the why is it still requires human beings to be aligned. Um, focused on the customer heading in the same direction with agreed upon ways of working and executing, and that's still really hard. And so back to the question of why am I successful is I've put a lot of time into focusing on how, how to help a team, um, really do the thing, you know, those things have that customer focus and, and, and, you know, it'd be a whole nother series of podcasts, really probably to share. A lot of the little things that I've learned through trial and error and, you know, adopted from other people that make the difference. And I do think it's also worth noting that so much of what is, um, traditional. Instinctual, uh, and intuitive does not work when it comes to software development and the web and usability and design and those kinds of things. And so, if you just rely on sort of human intuition, that's why a lot of these websites don't work. That

Eric Brooke: 00:40:33

a lot of people have cognitive biases that they don't know how to manage them. Like categorization, we love to categorize things, label things, and that's not always helpful. Um, and actually can cause more problems. So thank you for that. Um, so thinking about what are you seeing in the wider tech market today?

Barnaby Dorfman: 00:40:54

I think there are a number of things that are worth noting. Uh, I, I, I mean, I think, so obviously Gen AI, super hot topic. I think that it is. In a place that's similar to, you know, like what happened, let's say with cloud computing, um, whatever, however long, 15, 20 years ago that really started, uh, where the hype exceeded the reality for some initial period. And then there was a little bit of a like, Hey, you know what marketers are just putting that name on something that's not really a cloud. There's nothing cloud about that, whatever. Um, this is, you know, a lot of people concluded wrongly that, that it really was just fluff. In the long run, cloud truly represented a step function in the way that we, um, do our work. And I would say that the long term impact has exceeded the initial hype. I think that where we're at right now, I mean, Chet GPT is 14 months old. Um, The hype last year was, you know, massive. The hype now is massive, but I'm starting to see people like, Oh, it's not really that big a deal or whatever. And, you know, and, and we have yet to see the killer app beyond chat GPT, right? Like in terms of something that's really, really changing the world, I think we're going to see some killer apps by before the end of this calendar year. Um, and I, I think it's going to be, you know, in a variety of areas, but for example, customer service and, and chatbots replacing the Madlibs chatbots with something that. Actually could be better than humans, um, because you've trained it on all of your, your, your documentation, your actual code, every single support ticket you've ever had, um, that, that chat bot powered by an LLM is going to do better than somebody who had, you know, maybe a few days of training, you know, in a culture different than where the user is, et cetera. Um, so that's, that's something I'm excited about, like lots of people, but that's her buying out my, my thought. Those are my thoughts on where that thing is. I think the others were in an interesting place. You know, there were obviously a lot of layoffs last year. We've seen, I think a lot of people thought, okay, that's over, but then we've seen a bunch more this year. Some of it tied to a transition from kind of shutting down things that weren't actually working. I mean, you just think about like how big Alexa, you know, the, the, the Alexa team was at Amazon, but you know, and the equivalent, you know, at Google and Siri at Apple, it just completely missed the boat and did not. You know, get it done relative to what the LLMs are capable of doing. So there's thousands of people who were toiling away on things that were pointing in the right, wrong direction. Um, and I think, you know, we also, we had, I mean, I've been through enough recessions that I remember the dot com bubble burst, you know, very, very vividly. And that was a long, low slog back. And then the Great Recession, again, Pretty long, slow slog back. And then we didn't really have any sort of a correction as an industry, um, or an economy. Um, you know, since say 2012 ish, up until kind of last year, and these, you know, these things were companies would just hire massive teams to prevent competitors from getting them and then they'd have them doing work that was of questionable internal value. Um, so I think this correction was needed. Ultimately will be healthy, but it's also led to a lot of froth, a lot of froth in the marketplace. I, you know, I, I, um, I currently am, uh, you know, kind of doing some advisory work and, and kind of part-time fractional C-P-T-O-C-T-O type jobs. So I'm talking to a lot of people and I, you know, I, I company after company, I see, you know, they're on LinkedIn, you know, premium, they've got the insights graph, and, you know, the, the hiring curve is basically an inverted v. Over and over and over again. I see, you know, it's it went from 200 to 400 down to 250 or some version of that, you know, whatever scale and, um, you know, I talked to a CEO recently who, uh, you know, product that I've used, um, they, uh, raised a bunch of money kind of in that during the pandemic, uh, sort of. Everything's shifting to online. Everything's got to be automated more so than before. And just this displacement caused money to flow in new directions. And so this company was the benefactor of that raised. It's lots of money, got a unicorn status valuation, uh, and the CEO is like, I spent 80 million, you know, dollars on, uh, you know, basically development, you know, over a period. And I have essentially nothing to show for it. Uh, can you come help me figure out why and how I fix it? And I think there's a lot of that out there and just general kind of froth, um, around it. Thanks. Do you know, do I, what kinds of people do I need, um, what are the market opportunities with gen AI and how do I adapt to the sort of new environment? And again, trends are trends, right? Like the trend, you know, there, there I've been in, I've been in a board meeting where an investor said, I just invested a huge amount of money and it's not for you to earn interest. Well, at the time interest rates were basically zero and everything was about growth. I guarantee you that same investors like I want to see your layoff plan, uh, you know, if you don't need to spend it, you know, you can get 5 percent on your money. Um, so, you know, you got to sort of play with what is happening in the environment today. And so those are some of the dynamics that we're dealing with. And as interest rates come down, um. That will change the dynamics of investment and the funding environment. That's, I guess, that's another piece that I would mention is that a lot of folks are made around is fully keyed into is when, you know, when interest rates are essentially zero, high net worth individuals, um, retirement funds, sovereign funds from governments, et cetera, um, they pour their money into private equity, even though private equity, you know, the top end, you know, 20, 30 percent of Um, you know, the middle tier is going to be 10, 12 and the bottom quartile, you know, it can be 5 percent or below. And so with when you can get five or six or even higher percent risk free without also the long term commitment, because those funds, you know, you're getting in that for 5, 10 plus years, five quick 10, 10 years. Um, The risk reward ratio is out of whack. And so much of what we all live on in the tech industry is the flow of investment from VC and PE. But I think, you know, because inflation is moderated, you know, so many people are counting on betting on is interest rates will come down this year, long term rates have already come down. Um, and then, you know, the investment flow will, the spigot will open up again. Um, so that's another piece I would say that I'm seeing out there. Cool. Hopefulness.

Eric Brooke: 00:48:05

That's great to hear. Um, Barnaby, thank you. My last question for you is what do you do for fun?

Barnaby Dorfman: 00:48:12

I had a long list of things I do for fun. I love to cook. Um, I've always been into food, uh, born and raised in New York City. And, you know, sort of my family really embraced the multicultural, uh, culinary aspects of the city. And I've. Traveled and lived in a bunch of parts of the world. And I, I, I like to say that, um, cooking is the only perfect art form because it is the only art form that uses all of the human senses of, you know, taste, sight, sound, even the crunch, um, obviously the smell, uh, you know, all of that matters. Uh, so I just, and it's infinite, right? There's always something new to try to learn. Uh, and, um, It is a great way of connecting with people and, uh, spending time and learning. And it's a little bit also, I think because we eat every day and multiple times a day as humans, typically, um, it's kind of like the ability. One of the things I love about working on the web is the ability to do, to run experiments, AB tests, right. If you've got enough traffic, you know, you think it should be around, but I think it should be a square button. Let's just, you know, let's AB test it. And whoever's right is right. Well, you know, in my family, you know, I. Try addition and everybody hates it. Maybe not going to do it again. Or maybe everybody's like, well, just lay off the garlic or, you know, whatever it is, like, try it again. Oh, everybody loves it. It's got that same sort of. Opportunity for experimentation and learning. Uh, that's multi sort of multidimensional that I enjoy.

Eric Brooke: 00:49:41

Awesome. Barnaby, thank you very much for your time today and the wisdom and all of the journey that you've shared. Deeply appreciate

Barnaby Dorfman: 00:49:48

it. Thank you. Thank you. My pleasure.

Tim Winkler: 00:50:11

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