Dana Lawson, CTO at Netlify

Speaker 0: But I do feel like that connection between creativity and artistry is what developers and technologists crave. Like, what are we doing? We're we're creating a digital world that is for humans to have a presentation layer to experience new and amazing things, and that's that's living.

Speaker 1: Hey, everyone. Welcome back to another episode of Trace Talks. We have a wonderful guest today. I'll let you introduce yourself, Dana. But today, we have Dana, who is, an amazing person.

So go ahead and introduce yourself.

Speaker 0: Howdy, y'all. Dana Lawson, CTO of Netlify, x GitHub, x Envisioner, x NewRelecan, x all the things. Great to be on the show. Thanks for having me, Pedro and John.

Speaker 2: Yeah. Absolutely.

Speaker 1: Of course. We had a great, intro conversation a couple weeks ago with your with you and really enjoyed the conversation. But for those of us who or for those of, the people who might be listening, why don't you let them know who Netlify is and kind of a little bit about what you do there?

Speaker 0: Netlify is a activities. My my daily oh, man. Oh, my daily activities. Spreadsheets and email. Duh.

I'm an executive. No. Netlify is a composable web platform. We help enable web developers and creators alike, take their idea all the way to production. So we connect to your Git repositories.

No matter what flavor of Git you use, we help you build, design, deploy with a global CDN network with, performance. It's pretty fun. And my daily duties I mean, I'm chief technology officer, but that means a lot of different stuff to a lot of different people. And as I joke, it is mainly spreadsheets and and emails and videos. But, honestly, my job is to inspire, lead, and and break through all the problems that we have, building amazing and compelling software.

So I have the product design, and engineering teams. We all work together under my organization.

Speaker 2: Amazing. And I know that, you know, now you're you're an inspiring leader. You're a CTO of a company, but it, obviously wasn't always that way. There was, like, a path to get there. And I think you came from a much different background before.

Right? We had a call about you being sort of an artist and that. So I'd love to hear sort of where your career started and your sort of trajectory and how you got here as a CTO.

Speaker 0: I mean, you know, I am so blessed to be surrounded with a lot of, like, the Silicon Valley greats. You know? And most of them went to MIT and Stanford, but not all of them. Some of them are dropouts too. But I did have the trajectory.

You know, when I started out being a nerd, I was I was really into art. You know? I mean, I've always loved science and math because I'm one of those people. But, I grew up in Southeast New Mexico, Texas, and I was like, I'm gonna be Georgia O'Keefe. I'm gonna paint.

I'm gonna draw. Parents weren't really thrilled about going to college for painting and drawing because that means being a poor starving artist. You gotta be really good. In the art world, you gotta be like you first of all, you gotta know some people.

Speaker 1: Especially when you're alive.

Speaker 0: Yeah. And you gotta be good. And I was mediocre and knew nobody. So, like, my odds weren't very good, and this is pre Internet. And so on a crazy whim, you know, I was like, what am I gonna do with my life?

I joined the US army. How you go from art art school to the army? Hello? I'm a multifaceted person. And I really letters

Speaker 1: are the same. Right? Two letters, art army?

Speaker 0: I think that, you know, like, you know, it wasn't always great with spelling. I was more of a math person. I should have looked a little little bit closer. But, you know, it's funny because, like, you go and you sign up for the military in the United States, they make you take this test. Well, they used back in the day.

I think they still do. I mean, I don't do army research anymore. It's called the ASVAB. And, essentially, it determines your military occupation. Right?

Like, what are you good at? I scored really good on the math stuff. They didn't have an art section. I would have dominated. Go fig.

They didn't have it. And this job came up in the late nineties. It's like information systems operator analysis developer, like everything tech because they didn't know what to call it. And I was like, computers need air conditioning. And here I am.

Here I am because of that fateful choice of choosing air conditioning because computers needed it, my own, my own need to be comfortable. But, honestly, I loved it. I went to the US computer science school that they had made. I don't know if it's still there. It was in Georgia at the time, and it was an immersive, like, 12 months of, like, bare bones networking to all the way to, like, sea language.

And then you get out and you're like, okay. And I got I got positioned to, to really create and administer all the military applications. And so from there, it's like, wow. But long story even longer, you know, I was IC. I've been I've been everything you can be in in developing and creating software.

I was a sysadmin. I was dev ops. I was a SRE. Every letter in the alphabet that we attach to, to what our jobs are, I've done them like QA, TPM, TIM, PM. And, you know, I I just got bit with that leadership bug, and I really started going down the path of leading teams and not becoming an individual contributor, and then here we are.

Speaker 1: Yeah. That's a interesting way to get into a career. There's air conditioning there, so I'm gonna jump in. Did you find that that transition from being an artist, a former art student artist, and then going into army and tech, was that an easy transition for you? Did you really enjoy it?

Did you pick it up quickly, or did you just really enjoy the air conditioning?

Speaker 0: I mean, one, I'm in Portland, Oregon, and and today is gonna be a 100 degrees. And I think this entire city is, like, scared. I mean, I'm looking out. I'm not going out today. It never gets this hot.

But no. I mean, you know, I was already doing a lot of stuff in Adobe, like the early Adobe days in graphic arts, and, like, I had back back when Microsoft and front page. I remember that. Did y'all do any of that? Oh, it's probably a file.

I love it. I love it too. Oh, well then, you know, so like I did web design when there wasn't like, you didn't know anything. Like we all know how to make websites. Like I was making some geo cities.

I was doing that. I was a webmaster y'all. Alright? So but I always looked at through this lens of, like, being able to be creative. Like, that is all we actually are.

Like, maybe it's not you hands to keyboards and you're taking those requirements, but a lot of the times, those early ideas are all you. And the way that we write code is individual to us even though the AIs come and take our jobs. It still is because you get to determine what goes where, how it functions, and how the end user is gonna deal with it. And, like, it can be language frameworks. I mean, you could do it in so many different ways, and it wasn't a weird push for me.

It was actually really natural. I was just like, but I'm very curious. I'm one of those people that, like, it don't matter where I'm at. I'm gonna have a good time, and it's very annoying to other people. But to me, I'm like, you know what?

That's just how I roll. You know? Because it's not the place you are. It's the people and experiences you have and and who you're with. And so I loved it.

I I I I was just like, this is fascinating. I never, in a in a in my wildest dreams, ever thought I would be doing what I got to do. And getting to, like, live from man, the first job they gave me in the military was changing backup tapes. Like, they didn't trust me to do shit except change tapes, and they were smart because I had Yeah. I had ruined a bunch of servers at one point, but that's a whole different story.

And so they're like, Lawson, you get to change the tapes. And so I got to incrementally, like, grow my skill set and apply it. And it was great. It was a great job. But I do feel like that connection between creativity and artistry is what developers and technologists crave.

Like, what are we doing? We're we're creating a digital world that is for humans to have a presentation layer to experience new and amazing things, and that's that's living.

Speaker 2: Yeah. Yeah. And I I I feel that most of the people we talk to as well, on this podcast and otherwise just in our daily sales life. We're speaking to a highly technical audience, you know, selling our product, and most of them are creatives in some capacity. A lot of musicians, tons of musicians.

I think almost everyone at Directus plays some kind of musical instrument. So I I definitely agree there. So what was that like? The yeah. Go ahead, John.

Speaker 1: Well, I just wanna really pause to to call out that you changed backup tapes. When I first got into tech and I realized that backups were being kept on tapes, literal tapes, I was so shocked because I I was selling data center equipment. I'm like, wait a second. Mhmm. People are still backing up on tapes.

So Oh, yeah. I just had to call that out that that that brought back some memories from my past days that and probably still to this day. I know some obvious obviously, digital backups are huge, but, I'm impressed that you were changing those actual tapes because I always I knew those people existed, but you were one of them.

Speaker 0: Oh, man. It's it's it it was not a glamorous job. You literally go into a colo with a tray, and, you're like, it's the a day because you have a b tapes. Alright? And there's a software called Veritas.

No. It's this software called Veritas. Oh my gosh. People are gonna have to go Google this shit. Alright.

Speaker 1: I sold that stuff.

Speaker 0: You sold Veritas. Oh, man. No. But, yeah, it is. It is amazing.

Yeah. Tapes. Well, we we should have a whole, like, discussion one day about, like, tech of past, like, the tech museum.

Speaker 1: Yeah. Sorry, Pedro. Go ahead.

Speaker 2: I I didn't remember because I had

Speaker 1: to call it out.

Speaker 2: Yeah. No. Absolutely. Maybe that's another another show we could put on Directus TV digging into the tech past. You know?

Speaker 0: Yeah.

Speaker 2: No. That's awesome. And so what was that moment that for you kind of transitioning from an individual contributor to a manager? You you'd mentioned you sort of got into leadership. You really liked leading teams.

What was that initial pivot point, from being an individual contributor to a leader?

Speaker 0: You know, I mean, I think a lot of of people that I've met that have been in these positions, there's something that honestly is natural that comes with it. And for me, it wasn't this, like, I wanna be a manager. I absolutely did not wanna tell people what to do. I can't like people telling me what to do, believe it or not. But I just wouldn't stop my mouth from running.

And I was like, we should do this. We should do this. Here's why. And I'm like, on my soapbox just saying, here's why we're here's here's how we're gonna unlock this. And they're like, listen.

Why don't you just tell everybody what to do? You're doing it anyway. They don't want a sideline manager. You might as well just be it. And I was like, well, you know, I've never done that.

I mean, I've done, I guess, different leadership stuff because naturally you have those opportunities in the military that kind of force you into, like, these these different things to do. And I don't know. I've had jobs and jobs of days past. And, I just feel like, you know, at that moment, I was like, oh, okay. And from there, it was just like, okay.

How do I change this directory? The hardest transition, I think, really was, you know, when you become into leadership and you start leading teams, a lot of us have been individual contributors, and you're like, wait a minute. And and if you have a good culture, I hate that us versus them culture. It's like your boss is just an adult too trying to make money. There ain't no us versus them.

I mean, if there is, like, go somewhere else. And so I really just would approach it. The hardest part for me was not separating myself and saying, oh, you know, now this is my new role, but more of, like, this isn't my role. Like, that's not your like, for me, it was like that that's not your job no more. And that's still hard for me where you could get so immersed with just, like, in the flow zone of of writing code.

And you're like, as a leader, like, yeah. You can as a frontline manager, you may do some of that, but that's not your job no more. Like, if you wanna be great, your job is to empower, enable, align, and motivate, and realize what your role is. And maybe you're a team where you're a player coach and you get to still do that, but that's not your primary. Your engineers, that's their primary.

And that was the hardest transition for me making that. But to get to that, I mean, it kinda came a little naturally. And then from there, it just was like that that hunger to take on more. And, you know, it was funny because, again, I never expected, like, you know, a lot of people are like, one day, I will run my own company or I'm gonna be a CEO. I was like, no way.

I never thought that. I just always wanted to do amazing things with amazing people and and hopefully change the world. Like, to me, that's more important. But, yeah, I mean, it wasn't it wasn't a hard trajectory. I think, again, like, separating what you used to do seems to be the hardest part for people that transition.

And there's only been, like, 1 or 2 times in my career where I've ever met anybody that was like, I wanna be a manager. And I'm like, what? Like, that's your goal? Like, why? Like, why do you wanna do that?

And and usually, when they wanna be a manager and they're that resound, it's for the wrong reasons, like, straight up. It's not it not all the time, but I mean, I've heard one person's like, oh, I wanna be a manager. So why do you wanna be a manager? Because I could tell everybody what to do, and I I could quit fighting battles and, like, we'll just I could just get it done. And I was like, what planet do you live in?

Like, because people I said I said, welcome to management. Your job is just fighting battles and trying to get, you know, people to to to agree and commit or disagree and commit, but commit is your out is your long goal. And so, like, it's you really feel like a used car salesman. Half the time going like, no. So I no.

That price is not gonna work. I'm sorry. This is not gonna work. Yeah. See, it's not if you have a fantasy of command and control and leadership, like, again, you gotta find that the culture that that's how that's how they vibe.

They're out there. But like most places where a lot of people are happy to work, they don't want that.

Speaker 1: Yeah. You mentioned putting down some of the tasks that you had previously done as an IC and and finding that a little bit of a struggle to put those tasks down. And then you also mentioned kind of fitting right into leadership. Was that was there any learning curve, or is your personality one where you whatever the task is on your plate, you'll figure out and do it? And then I guess the second part of that question is, were there parts?

Because you you didn't go in searching for leadership. So did you get into leadership and managing teams and say, oh, man. This spreadsheet stuff sucks. You know? Like, I don't like this part, but I'll do it anyways.

But so I guess what was that learning curve like, and were there parts where you're like, oh, I didn't even know I'd have to do this stuff?

Speaker 0: Oh, man. You know, I think the actual learning curve is is not knowing what you do need to shift and having to grow into that on the other side of the house because you can really look really shallowly and be like, well, what's the big difference? You're just breaking down tasks and giving projects out. That's what leadership is. Absolutely not.

I think the learning curve is really dialing into, okay, well, how do I really start having effective communication? Like, obviously, I was somewhat good at it. I'm now in this position, but how do I refine it? How do I talk to different personalities? Because as a tech leader, an IC, you're just talking to mostly other engineers, sometimes product people, but they're still your people.

Right? Now when you become into leadership, you have different stakeholders. And I think the biggest opportunity to learn is to understand how to speak their language, how to communicate effectively, and how to distill that information down so that there's still alignment between both parties so that you're not communicating in a way where this side hears something different than this side. And sometimes that can happen because breaking down really audacious technical things for people that are more on the business side, sometimes when they're motivated by different things, they'll hinder different things. And the example I give is, like, you know, let's say a success manager comes to you and says, so where are we at with that bug?

And and and the engineer is like, well, we're gonna be code complete in 2 days, and we're gonna ship it tomorrow. Great. You're shipping it tomorrow. It's like, no. No.

No. No. No. Stop. Stop.

Stop. Stop. Yes. Technically, we are shipping it into staging and integration tomorrow, and there's still more behind that. And what you mean by code complete means something different to go to market.

So you have to be really that translator or you're gonna cause friction. And as a manager, guess what your only job really, really, really, really is, is to remove friction. At the at the end of the day, your job is to remove friction. And the way that you do that is to to the the the morning's problems that cascade into the night. And you're constantly being agile and saying, where do I help people not run into anything that's impeding them from what they're trying to do?

That's really all you gotta do. So I think that was the hardest kind of, like, is is is and then and then as you go further into it, right, like your frontline manager, you're like, okay. Maybe I'm talking to support. Maybe I'm talking to marketing. You go to director.

Now the table stakes are like, now you're now you're learning the economics of operating and running a business. Right? K? Now it's like contribution margins, cost of goods sold, CapEx, OPEX, all these fin financial terms that you think we have acronyms? Go talk to an accountant.

They have just as many. K? And sales, I don't even know if you're talking about half time. BDR, SDR. I'm like, I don't know.

I do now though, but that's the stuff that like as an engineer, you don't learn that. Nobody taught there's no school to teach. There's no engine. We can go like I said, you can go to Stanford, MIT. They ain't gonna teach you about how to look at a financial forecast weighted against 2 growth motions and and outputs and forecasted.

Like, it's all things that maybe you took a a side business class, but most of the time you're learning it. You're learning it on the job as you as you move up that corporate ladder.

Speaker 2: Yeah. That's wild. I think that, you know, I I just personally, that's something that I've been focused on a lot is really understanding different points of view, and it's something that I sort of I don't know. I mean, maybe it's the Libra in me just trying to, like, balance everyone and play like the the diplomat in most situations. But what do you think that you pull from, to to have that sort of knowledge now and being that translator and being able to effectively communicate and and be that diplomat between, you know, your teams?

Speaker 0: I mean, I have a big mouth, Pedro, so, like, you wouldn't believe this, but, like, active listening is so important and really just practicing on my mind runs a 1000000 1000000 miles a minute. Like, I am like I've I've main I've I've been able to challenge my ADHD into something productive, which is good, not good. Okay? But it's really about taking that moment and forcing myself to really go into active listening mode and pushing against those instinctual, I need to go. I need to execute.

I need to push because you're so trained to have maximum productivity. And and in software engineering, it's about that tempo of delivery. And then when you're on the other side and you're working through really how do I express this to 100 of 1000 of users and get to start internally with my team first, like, it it's isn't it is again an art. It is it is something that you have to inherently start to develop. And what I do is I try to spend time just learning their business, understanding their workflows, putting on that product research mindset that, you know, we have as engineers and technologists to say, well, if I wanted to understand my ideal customer profile, well, my ideal customer right now is my partner over here on this side of the business.

How do they work? How do they operate? How can I meet them where they are? And so also just, like, talking to other mentors and, like, people and, like, getting advice and, like, seeking feedback. I don't think I've ever not had a a, you know, an employer review tell me you're too verbose.

I mean, it's a work in progress. I'll always be too verbose. But, like, really taking in that feedback and and trying to understand where we can be better, so that self reflection, those 3 sixties, so all those things that you can do and bringing them in together to understand. But I think active listening, really, which there's a whole bunch of techniques out there to do that.

Speaker 2: No. Absolutely. And and do you think that your your experience and your previous background in, you know, the alphabet soup of all the roles has helped in that? Like, you've had a sort of understand the different roles that you that you manage and the different roles that you sort of sell to internally and understand the languages that they speak?

Speaker 0: Oh, yeah. I mean, I love it. That's where I always encourage people to get out of their comfort zone. Like, do it. Like, I've done so many things that I never won obviously, was qualified for.

So thank you to all those people out there that believed in me, because, like, I don't know if I would've put myself in that position, but here we are. And it's really about taking opportunities and and and finding those spaces within what you know and filling the gap. Right? Like, it's really human nature to double down in the areas where we're comfortable, where we can sit and say, I can just crush it. And in times of duress, we do that.

We seek that comfort in in in repetitiveness and consistency. I don't like it. I get bored. I like it sometimes. And most of the time, like, when I'm getting comfortable, I'm like, oh my gosh, I gotta go solve.

I gotta go find my next problem. And so I push and I've had the opportunity through the alphabet soup to do stuff that was kind of orthogonal to what I already had known. Like I got a wonderful opportunity to do business development, like pure business development. And I when I got tapped to do that, I was like, are you sure? I was like, I have been an I have been an engineering leader for a 1000000 years.

You want me to do biz dev? Like, that's on the other it is on the other side of the house. I do not even know. Yeah. But they're like, no.

Our business is talking to developer. Our business is expansion. Our business is helping, you know, really the value of our platform be open to everyone. And so when you think of business development, there's nobody better than a technologist that's right in it sometimes. However, you still need that other side of business acumen and that understanding of the sales operation and motion to be able to be effective because at the end of the day, the stakes are different, and and it's just a different type of ball game than delivering software.

And that experience alone, I'm like, like, you can't go to you you can't go to school to get to learn that. And to me, it just strengthens that the inner team empathy that you need to have a startup because you're all pushing for the same goal and it's gonna be uncomfortable even if you are in your sweet spot. You you're gonna have moments in your trajectory where you're like, what am I doing? Why am I doing this? And and having empathy holistically helps everybody be better to deliver what they're doing.

You can't just have a well oiled machine on one side of your house and then the other not be working or it's all gonna fail.

Speaker 2: No. I I absolutely agree in it. And, you know, I've seen that at the different companies that I've been in. Sometimes it's hard to align, especially when it's the technical teams versus the less technical teams and having being able to speak that common language. Is that something that obviously, they don't teach that in school, like you've mentioned.

Is that something that you've taught as a manager to the the folks that you manage on the technical side, like balancing, you know, the technical acumen with the people skills and sort of the the goals of the business, which are, you know, ultimately to to earn revenue and keep everyone employed?

Speaker 0: Heck. Yeah. I mean, I think that's my number one job. Right? Like, I'm always trying to get my leaders to work me out of a job.

Like, the best the best, you know, example of leadership is the person behind you taking your job or them going on to do the job you were doing. That's it. That's all I live for is to see see the people that I had the opportunity to partner with, go on and do bigger, better things, and me having a small little piece of that narrative. And hopefully being positive. I know it ain't all roses, but I think that's something that you have to do because it doesn't, you know, I talk about, oh, it all comes naturally.

This is the part of the house that don't come naturally. This is the part where you have to be curious. You have to have your humility low and do a little homework, do a little research, and and try to meet them in the common ground. And I try to do that. Like, a lot of us have been utilizing, you know, objectives, key results, or other frameworks, and they can get so convoluted with with what you see the lens of the world.

And as an executive, it's about that abstraction so that everybody can understand it. If they can't, then why why? And so from a manager training perspective, manager enablement is so important unless, you know, I don't think a lot of places are gonna get managers and be like, listen. I expect you to be a career manager. So, like, I ain't gonna teach you nothing new.

Just keep the job rolling. Like, I don't know. I've been around for a hot minute. That's how it was in my day when we had cubicle cities. You were just, like, waiting for somebody to retire to get your job, to get the next job.

It's not like that, and it hasn't been like that. And so, again, as a leader, if you have your goal set on really raising the bar on your team and getting them to the next level, it's finding those opportunities and those skill gaps and then teaching them that that common language. And there's so many there's so many darn resources because it's not just business speak, but when you have also a growing company and a global customer base, you also need to know culturally, like, the nuances. And there's some great books out there. I always recommend the cultural map.

It's it's a book that helps you distinguish really how if you're like an American, how you show up or Western society. And it's really an interesting read. And I think those are some of the things that I try to encourage my leadership team as they're working on that voice is be customer centric, internal and external. And that means business acumen and speak, but also just human to human and understanding how they how they were brought up in this world and how they culturally represent themselves.

Speaker 1: So I think it goes

Speaker 0: hand in hand.

Speaker 2: So many nuances to it because, you know, yeah, it's not just internally between the different teams and the way that they speak, but also culturally, you know, you've got companies that are now global with remote work just being sort of the the default in a lot of these areas. So maintaining that company culture is also important, and these small little things can cause a rub between, you know, the Americans and the Europeans. They have totally different styles of work life balance and and culture and everything. So, yeah, I think that's that's really important. Are there any specific, like, exercises or resources that, or, you know, strategies that you implement within your teams to try and keep that cohesive

Speaker 0: culture. I mean, I mean, definitely, you know, we we try to do enablements and trainings, not just for managers, but for people, and they cross the chasm from technical skills to soft skills. Like, you need both, whether it's public speaking. Because public speaking is actually another good opportunity to refine your message house, your internal message house. If you can't say it in an elevator pitch, then you're probably not speaking common enough language so that people can understand your value.

So I always recommend, like, get some speaker training. Believe it or not, I've had it. They teach you some tips. They're really, really good. But in addition to that, I would also say that, you know, some good resources would be writing things down with clear lines of ownership to also help clear up some of the ambiguity.

Because, again, when you're talking about multicultural teams, from many, many different countries and and and English is second language for peeps. I mean, at Netlify, I think we have 17 countries represented in our in our little amazing startup. That's a lot of different people from a lot of different places doing a lot of different things. As we utilize tools like the DAISY, drivers, approvers, contributors, inform, and these frameworks so that you can drive decision making. And sometimes you have to leverage just written.

Because maybe maybe maybe maybe you're having a block where there's friction within the the spoken communication. A lot of people can read better than they can speak, self included. Right? Like, I can I can I can speak I can read Spanish all day and I can speak it? But, I think that there's those opportunities too and other things that you can utilize to find that alignment.

So I'm a big fan of DCs and RACES to really ensure you have clear ownership and that that's been, understood. And then also, you know, really just pushing a written culture. Like, don't keep stuff in the ether. And there's so many come on now. Like, there's so many tools that do it for you.

Like, 4 years ago, we didn't have a little AI recorder that did a transcript and a summary. You can do all that now. Don't tell me you can't. And I I tell people, I'm like, you're not comfortable. I don't know.

Go use go go go use your your model or your choice, your chatbot of choice. I don't care.

Speaker 2: It's cool. I training even as a training tool. Right? Like, you can have conversations with these things, and that's only improving. I mean, I've done job interviews even where I'm like, simulate this,

Speaker 0: Yes.

Speaker 2: Simulate. You're the you're the you're interviewing me for this role. Here's the resume. Copy paste. Right?

And have a little conversation. Those those types of things can even be be pretty

Speaker 0: Use them. Use the tools. Like, we're all learning them. And, like, again, that's a double edged sword. You're like, I get to understand this, whatever we're saying AI is and how to be better.

And I think, you know, you gotta be a technophile. You know, that's why you're in this role. You gotta stay on the latest. You gotta love it. You gotta know it.

And I I do. I encourage it. I'm like, go. Go go go go ask go ask go ask the AI for you.

Speaker 1: At the

Speaker 2: end of the day, like, refining your communication skill set. I I keep seeing these ads for, like, Bob Iger's master class or whatever. I think that the thing he's saying in these ads is just like your your vision or your idea is only as good as your ability to articulate it. And, you know, back to your point, it's like having that ability to to communicate those ideas. If you can't do it verbally, like, at least writing them down and continuing to practice those so that you can win over your team so you could become a better a better leader, better even a better individual contributor.

Like, everyone's got ideas. So, your ability to communicate that with others, I think, is is probably the point here.

Speaker 0: You better believe it. I mean, shoot. Like, a lot of, a lot of engineers have that that leadership charisma, and they want to refine that side of the house. Let them, like that's the I mean, again, I think that comes back to the harder part. You know, we are so so lucky to have this advanced toolset around us that we can go and source information.

We can ask questions. We can autofill. We can move, but you gotta put in the work on the other side. And so, like, I definitely see, you know, an opportunity with getting people more comfortable and, again, utilizing the tool sets to do so. And that's where, you know, like you said, using it to, like, mock interview.

Like, yes. Go do that. It's it it some of them are good enough. I mean, some of them are are not great enough, but it gives you also some which is interesting, I think, because people were like, oh, I don't trust the AI and the models, but it's private. It it's better than going into like, can we role play in Slack?

Like, nobody wants to do that. Like, you

Speaker 2: know using even, like, there's an app that I've been using called Sonja. I actually spoke to the team a couple weeks ago. They were gathering some feedback, but it's an AI therapy app. And what I kind of started to realize, and maybe this is what some of these apps are sort of you know, they've they've modeled everything after their CBT techniques, and it has, like, an in-depth knowledge of, therapeutic techniques. But what I've realized is there's this barrier when you're talking to a human.

Obviously, you're presenting the best version of yourself. You're not being as raw as you could be.

Speaker 1: Mhmm. And

Speaker 2: there's always some sort of, you know, I don't know, like subjectivism on the other side. Mhmm. And you know that somebody's, you know, judging you in a way where when you talk to the AI, there's zero judgment. You're talking to a computer. Your mind sort of knows it.

So you speak to it a little differently. And for something like therapy or something like training, I remember back in college we used to do these sales role plays. Those things are terrifying. You're doing it in front of the class with the professor and it's like, you know, you're getting graded on this. And, to do that with AI, I think would be, you know, it's just such a such an improvement.

Even if it's not perfect, it's it's still going to at least let you drop the guard, speak in your natural voice, and and learn effectively.

Speaker 1: Yeah. I I also think with AI tools and tools in general or I guess when you're dealing with humans, people are afraid to make mistakes in front of other humans. And so with an AI tool or a software tool, you're like, oh, I just made a mistake. I can just redo it again. You know, as a salesperson or as a if I do code wrong and I'm just testing it, it's easy to it's easy to make a mistake.

So, Dana, do you find that you know, you you mentioned encouraging people to go try a ai tools and encouraging people to go test new things. Do you find that after you encourage them a couple times, they're more more willing to go and try new things on their own, or they're more willing to kind of understand that making mistakes is okay. Because similar to what you're saying, Pedro, is when I try something with an AI tool and I make a mistake, it's, oh, next turn. Let's go to the next turn. So I feel like the the stigma of making mistakes is removed when you when you have a barrier removed like that.

So do you encourage your team members, Dana, to go and try new things and then find them down the road trying more and more things without having to be encouraged to go try those things?

Speaker 0: Oh, definitely, man. I love growth mindset. Like, you know, and and and what it comes down to is putting that human imposter syndrome, shame, or what other baggage you have thinking you ain't good enough down and building a place where people can do that and with psychological safety. Like, I totally I tell them all the time. I was like, y'all know that was written by AI because it's so it has all the right commas.

It's not saying random shit. It's it's actually a little bit more, more focused. And I just try as a leader to not not be embarrassed about it either. It's like, hey. I'm human too.

And I think, like, as as somebody that's creating and and producing the next set of advanced developer tools, you best know. Like, how how could you come? Like, where's your street cred? Like, people are using this stuff. I think you have to be really public about it, but also, like, be skeptical.

Like like, it's not perfect. I don't a 100% trust it either. But again, I think the benefits are more than the cons right now if you utilize it like a tool and really put the right boundaries of how you're using it to function. But again, for me as a leader, it's taking out the hesitation because you gotta remember. Right?

Like, tech has been through it. People are freaking like, you know, it's a doom scroll of, like, what's what's what's busted up in Silicon Valley right now. We're having a moment. I hope we're on the other side of it. Those feds cut that interest rate.

But I think, like, people are paranoid. Not everybody, but, you know, a lot of people are like, hey. You know, the economy's unstable. Like, I don't wanna be found out. I'm like, no way.

You're gonna be better. Like, if our number one goal again is to remove friction and increase productivity, you you should be doing your part. And, again, I don't think a lot of it is on the the hard skills of, like, utilizing these tool sets to be better. But on the soft skills, having those those moments to be like, I wanna ask it this really dumb question that maybe I wasn't comfortable going in Slack and asking it, or maybe I don't wanna even talk to my mentor. You know, 1, you know, don't put all your eggs into that AI basket and trust it out.

But I think as a guiding point, like, you're gonna start self serving those answers to yourself. And who doesn't wanna self serve? Like, nobody wants to talk I mean, I love talking to people because, like, that's what I do, and I'm from the 1900. But people this day and age, they won't be talking to nobody. Okay?

Yeah. And, like, that's cool. They're gonna talk to you when they want to, but they're gonna be more comfortable behind the keyboard. And we just have to embrace that and find different ways that people do communicate, whether it is short form video or, say, other AI tools, because that's the part that they don't teach you. And as being a leader, like, you have to pay attention to societal norms to understand how the current generation and the next are are taking in information, especially if you're a provider of how to do that.

And if we're in software, we all play a part in that experience.

Speaker 2: Yeah. I agree. And I I think that at the end of the day, you know, asking like you were saying, asking the AI, maybe some of the questions that you think might be dumb or, you know, getting sort of that, introductory knowledge about something out of the way. Maybe it does, if used correctly, break down the barriers between human to human connection where it's just like, you know what? I can actually do some of this research on my own in a very quick and concise way before I come to the table with my ideas or Yeah.

Yeah. So

Speaker 1: How how how important and I think this is a good a good thought on leadership. How important do you think it is to cultivate a a culture internally where, people aren't afraid to ask those what might be considered a stupid question. Because I've I've in the world of alphabet soup, there's so many acronyms you never know. And some people might be afraid to ask that question. What does BDR even mean?

Or, I mean, I hear acronyms all day. I don't know what they mean. So how important is it to build a culture where people are comfortable asking those questions to other humans? You know, you can go ask AI. But I think as a leader, you also wanna have that culture where people aren't afraid to ask questions because in the end, they just wanna be smarter.

Speaker 0: I mean, I think it's a it's a it's a big challenge, and you're always fighting it because, you know, as your team scales, you lose some of those opportunities for interpersonal relationships. Right? We've all heard Dunbar's number of a 150. You can't know everybody past that. I disagree.

I don't know. I came from a small town, and I knew everyone. But, but I do think that you it starts from the top. You know, your job as a leader, especially as an executive leader, is to set the tone and the pace. And, like, if you can show up and be your true authentic self, that gives people permission around you to do so.

And that means you're gonna probably f up. You're gonna say something that you're embarrassed about. Like, trust me. There's not a week that goes by that I'm just like, oh, Dana Lawson. Why did that come out of your mouth?

Why are you you? But you know what? I am me, and you're you, and I want you to be you at work because putting energy into being somebody else is taking away from your productivity. I ain't got time for that. I want you to spend those mental calories on on my stuff, which is getting shit done.

And I think you have to really, again, make it really known. You have to practice what you preach, and then give people those opportunities to find the psychological safety for them to be okay doing that. Again, you know, you can't you could just saunder people's experiences. You're not living them. They're theirs.

So you have to just kind of think about, well, how how would somebody that is 12 hours on the other side of the world take this information if they don't get it from me? How do we form a relationship? So again, establishing a written culture, you know, coming from the top down, being your true authentic self, that means messing up and being being a little scared sometimes you are. It's okay. That, like, that again, that gives permission to mess up too because humans are fallible.

But then finding other avenues where people can feel safe to be able to share and and communicate, whether it's surveys, Slack messages, written, town halls, q and a's. Do all the things because you're gonna need to do a wide splatter to get all the differences on how people need to be felt and heard. But, again, I also try to encourage that, like, one to 1, like, come and ask me. You know? I when my AI startup, AI Migos, you'll pay a premium for the real Dana Lawson.

What the day Dana bought, you know, I don't know, $20, I'll give you yes or no's. I joke about that, but, like, I want people to come to me because there are some things that you're just not gonna get on the other end, but utilize it as a tool. Practice. Like, get yourself comfortable. But when it comes from leadership, there's nothing more powerful than people see that you're authentic, genuine, and real.

Because I don't know. People can read it when you're full of baloney. Like, you think they ain't. They are. And maybe not everybody is, but you got some skeptics out there going like, that person full of shit.

And so, you know, I just say, don't be. Be you.

Speaker 2: Yeah. I love this idea of, like the Dana bot or like imagine the CTO at a company of thousands of people, that clearly it doesn't scale. You can't have a one on one conversations with everyone in the company or even the CEO or something like that. But cloning cloning that person's personality. And anyone now can have a one on one with the CEO at any time

Speaker 0: Oh, man.

Speaker 2: By the CTO. And if if you want to book the real thing, like, yeah, that that may happen as well, but anyone at every

Speaker 0: rag is gonna be crazy. Right? You're rag. You're like, wait a minute. No.

Let me let me make my rag on, lots of howdy's in y'alls. I but here's this you know, I think that that's gonna happen. That's what Hollywood's scared of. I don't blame them. But, you know, the the reality is is, like, you can't take away human to human.

And as a leader again, you just have to you have to stay in line with what's happening out there and who your people are and what's important to them. And right now, you know, it's it's not super easy. There's so much going on. I mean, we were all in a pandemic for 4 years. That was probably the hardest 4 years of leadership for a lot of people because everybody on the planet was fearful.

Nobody knew what was going on. And the stuff that you did know was happening, you didn't know what was really happening because there's so much information and be blasted at you. And it was a really interesting and I believe challenging time for a lot of people, you know, separating that work and life balance. And, like, the world's just gonna continue to get more complex, and there's always stuff going on. And, you know, you can only play your part and do so much.

So I always say, like, you know, like, while you're at work, I want you to not have to worry about some of those things, but focus in, get all those chores, get the friction out of place, and just feel good about producing. Because I think a lot of humans feel good when they produce because that's what working and living is, is seeing the output of your energy.

Speaker 1: Yeah. I think, yeah, I think sometimes that's important to remember is to still be able to contribute in certain ways. If we go back to a part at the beginning of this conversation, you mentioned having to learn to put down some things that you used to do as an IC. I've seen CTO calendars before, so you might not have any spare time these days. Do you still get to contribute at all?

Do you ever get to code or do anything fun kind of to go back into your IC role, Or is it just all spreadsheets these days?

Speaker 0: If if if I touch production, like, the team would be like, smack. Get out of here. Come in. What do you what are you doing in here? So no.

But no. I do on-site. Like, we're there's always cool stuff coming out. Right? Do I do it at work?

Mostly on the architectural level, I do a lot of, design work implementation and and that piece of it. But day to day, like, I get to I I have to try it out. Like, we release something. I'm the first person that's going down there, and I'm like, oh, look at this new Astro template. And I'm a terrible web developer.

Let me just be really real with y'all. Like, not my forte. More back end. But that's why I love doing web development because I'm so bad at it. And all these tools for they they they make it a little easier.

So I'm always trying that stuff out. I'm the 1st to give it a go. I'm like, oh, but, you know, I think you have to know what you're doing and pushing. Like, Netlify, we're always pushing out these core primitives that are really kind of nascent to specific things that you do within, how data transmits from the Internet to your computer and so forth. And there's so much to do on.

And so to really get that deep, you you gotta kinda get in there and know what's going on on on different levels of the stack. And so I think, again, you know, for myself, it can't just be all the fun soft stuff. As I say, I'm basically Napoleon Dynamite's brother Kip. I love people, but I love technology too. And so on my free time, because I get my peoples at work, believe it or not, I do a lot of stuff on the side and I'm always trying it out.

But, yeah, I mean, it's like bits and bobs there. I've gotten really good at macros though. So if you do need some spreadsheet food, like, you know, like, call me.

Speaker 1: You're entering those, Excel competitions. You're like, I know how to do that.

Speaker 0: Shoot. No. I'm like and now I'm I'm telling you, this is one area where I'm like, thank you AI. I'm like, no more. No more.

No mas. I mean, I could do it, but why would I? When I can be like, the train left the station at 2 PM and the other train left at 3 PM. And there's a person that gets I mean, I love it. AI is good at that kind of stuff.

Speaker 1: I hated those questions in school. It just was like, I don't it doesn't matter. Are they gonna crash into each other or not if they're not?

Speaker 0: It's like spreadsheets. You're like, if I take if I take column e and then I divide it by c and then I pivot it to your yeah. I know. I don't

Speaker 1: do it. Yeah. So so what's what's some of the favorite things that you've learned in your climbing to CTO? You know, what's some I guess, since this is kind of a podcast on leadership, what are some of the best leadership things that you've learned that you had no idea you would need to learn or maybe some things that you knew you weren't good at, but you've honed that that skill set? So what are some of the favorite things you've gotten great at over your your time?

Speaker 0: I would say, really, just I don't know if I'm great at it, but effective communication, I feel like I got a sweet spot for it. It's it's not been good. I mean, like I said, like, a a 1000000 miles a minute. So really practicing that focus, which I'm always still trying to refine my talking points. That's been one that I've been, like, you know, I feel kinda proud about where I've I've started at because it was a lot more.

Public speaking, like, you know, you never like, getting up and talking to a 5,000, 10000 person audience is is scary. Like, it is so scary. You're like, what am I doing up here? Some people are natural at it. There's like, put the mic on, and let's go.

And, like, you know, I play a natural at it, but I'm like, I'm scared. Every time I'm like, oh my god. Even this podcast this morning, I'm like, oh my god. Why am I doing a podcast?

Speaker 2: Couldn't tell when you're when you're giving a talk at the the Netlify conference. How

Speaker 0: was it? I know. I'm always scared. Always scared. But I would say, you know, public speaking is is one to crack over and, like, that's a hard one for leadership.

Public speaking alone, I just think it's it's not, you know, not natural to a lot of people and especially, like, hardcore technology is not very natural, but as leaders, you gotta be great at it. You gotta refine it. So it's all in that communication vein. And, the other part is just, like, humility. Right?

I'm a driven person. Like, we all have ego. We all wanna, like, crush it, win and be the best. Man, it don't take nothing but a big smack to show you, like, yeah, you ate perfect. You broke stuff and, like, it ain't all roses.

And I try to be, you know, I try to really have self reflection on how to show up and be better, but it takes a lot of humility because your ego can get in the way of your decision making. And, you know, sometimes when you're doing something so excited, you know, you you you you get that that tunnel vision. And I think as a leader, like, really taking those moments, self reflecting on how you show up, honing your communication, and putting your ego at the door is gonna make you effective. And, really, there's no secret recipe except, you know, continue to be smart, hungry, and humble with everything that you do, and and learn. You know?

Speaker 2: Yeah. That that's amazing. And, you know, being that we we kinda have a technical audience that views this podcast, individual contributors looking to make their way towards, you know, leadership and management. Are there any other, like, kinda as we come to the the end of this conversation, like, are there any other pieces of feedback besides the one that you've just given that that you'd like to leave with with the audience?

Speaker 0: I would tell the I would tell these ICs, like, talk to your freaking manager. Build that rapport. Be transparent about your goals. Like, don't listen to me. If you wanna be a manager to because you just wanna be a manager, like, go explore it.

Like, go. Even if it is for some reason that may not align with the reality, you're gonna learn by having that conversation out in the open. And if you're not sure, you can always start picking up some advanced things to give you those skill sets. Like, a lot of us have engineering levels and leadership levels, and they're in plus. As you go up and you get better, you get more natural leadership behaviors on your engineering levels as an IC and definitely on your manager levels.

And so there's this expectation once you go across the chasm of senior engineer, like, you should have some leadership capabilities because your job is not just to execute, but it's to break down and execute. And to be able to break down and execute, you have to talk to people, you have to motivate them, and you have to align them. You may not be their manager, but believe me, you are just as influential, if not more. And if you really want to drive towards a position where you have more strategic input from a wider scale, again, it's about bridging into those things that you hadn't done before and honing those crafts while you have them right now. Do it now and and and and, you know, form that relationship.

Managers aren't all scary. Some are pretty good. Most of them are pretty good. And if they're terrible, do what everybody else does. Leave them.

It's alright.

Speaker 1: Well, yeah, it's it's I think that's important. Communication is big no matter no matter whether it's at work or relationships or family or whatever it ends up being. I've I've really appreciated the conversation. I'm sure Pedro has as well. Is there any last minute things that you want to promote?

Maybe Netlify or your Etsy art store or analog tape backups?

Speaker 0: Oh, man. Analog tape backups. Yes. Come see me at veritas.dl. No.

No. Oh, I'm gonna go Google that after this. No. I do. As Pedro said, he saw me at the Netlify conference.

Netlify is having our own developer focused conference, October 2nd 3rd at the amazing Fairmont Hotel in San Francisco. So if any of y'all are listening and wanna come out and hang out with me and and see me pretend that I'm not scared even though I'm absolutely scared, apparently, Pedro said I was good at it. Thank you. That really actually helps. Come on down.

Come hang out with us. Tickets are on sale right now, and there's also, I heard, some codes out there. If somebody, you know, doesn't have all the cash to spend and still wants to come and hang. Awesome.

Speaker 2: Well, thanks so much for your time, Dana.

Speaker 1: Yeah. I really appreciate it. Don't think I've smiled as much in any of these podcasts. You're just amazing to talk to. So definitely appreciate the time.

Speaker 2: Thank you.

Speaker 0: Well, I had a great time too, y'all, and I hope you have a wonderful day. Thanks for having me on.