There’s a lot of talk about AI killing engineering jobs. Some jobs will change, and some will disappear. But we’ve been automating engineering work for decades, and somehow we keep finding more engineering to do.

At Web Summit 2026, I talked about how AI can raise the floor for developers, and what that means for juniors trying to break into the industry.

If you'd rather read than watch, the full transcript is below.

Transcript

0:03 Hi. Hello. Thanks so much for joining us and I'm so delighted to have this opportunity to speak with Avery because you know, I hear from young developers all the time as well as employers who are trying to figure out what it even means to build a tech career or to manage a team of developers in this world where

0:29 you know, I'm a I myself have no CS training and I now make software and of course there are lots of companies all over the world where people are vibe coding in ways that change what it means to be a developer. So Avery, you obviously have had a whole career. You're an engineer yourself. You've managed engineering teams and now you're in the position where you're I assume well, I went and looked at Tailscale's

0:52 current job ads. How how do you think the role and experience of building a career as an engineer has changed over the course of your career and in particular with the advent of AI? So yeah, you talked you talked about young developers. I'm I'm clearly not a young developer. I'm an old developer. So I've seen a lot of stuff. When I was

1:14 when I was going to university in the late 1990s, there was a program that I didn't take called software engineering that was competing with computer science. I actually ended up taking computer engineering, but we had a lot of discussions about what what is software engineering? This is like a new thing. Yeah. And we're in Canada and it's like engineering is actually a protected legal term in Canada. If you work for a company and you don't have an

1:36 engineering license, they have to call you a software developer. You can't be a software engineer in Canada unless you like meet these certain criteria. And so like at the time the joke was like look, there's no such thing as software engineering. Like if you're an engineer, right? And you're building a bridge and the bridge falls down, people are going to sue you, right? And if you're selling software, you just put in the license agreement. Yeah, sorry, it's not my fault. Haha,

1:59 you know, as is. Yeah. Right? And that that's the difference, right? But over time, we have actually figured out what real software engineering is in the intervening years, in the last like 25 years since then. Like, engineering is taking responsibility for your work and understanding that like everything's going to break eventually. And like, monitoring that and deciding when is it going to be okay for it to break and what are you going to do about the fact

2:20 that it's going to break. And so, to me, like software like software engineering is new. Right? What's different now is is suddenly the part of the job that was used to be called you called computer science or used to be called software developer, like a lot of that's disappearing, right? But the engineering part is exactly the same as it always was. Like, that's what people want to buy. They want to buy the guarantee that this thing is is when it if it and when

2:42 it falls apart is not going to kill people. So, I mean, I feel like that's a distinction that a lot of people are missing, as you can see if you use five-coded software. The it won't break thing seems to be a loosely held goal. Um you know, for folks who are are building and managing teams of developers now, where people come into the field, um you

3:08 know, how how much do you think developers still need to prioritize I almost want to call them like it's weird to describe coding as an old-timey skill, but it's starting to feel that way. I mean, do you still think that when you're hiring, you want somebody who knows how to write the lines of code or is the guarantee that it won't break about a different sort of a different

3:32 lens? So, I should say that the guarantee that it won't break is not is more like, you know, deciding how likely you want it to be to break, right? But my first year engineering class, I remember we did a uh they made us do this experiment where they gave us like a bunch of paper clips and you had to just bend it back and forth and then write down how many times it took before it snapped. And then you did that with like 20 paper clips, and then you had to like plot it on a curve,

3:55 right? And then and the guy like combined all of our answers, and he was like this like beautiful Gaussian curve. He was like, "Hey, this is reality. There is no paper clip that doesn't break. Some of them break in one bend, right? You have enough of them, like some of them are going to break in one bend, and some of them like didn't break until like 20 or 30 bends." And he said like, "You need to understand, they don't make paper clips that won't break until 100 or 1,000 bends because nobody

4:18 would buy them cuz they would be too expensive, right? The paper clips people want to buy are the ones that break, right? And so, that's what engineering is is understanding those constraints. And so, as somebody who's like building software, it's like, "Okay, like it's okay if I write code some crappy stuff that barely works if that meets the specification. If I'm writing an app for myself, right? No, it doesn't

4:42 matter. It can break and I'll just tell Claude to fix it again, right? If I'm trying to sell something to a billion users that searches the internet or whatever, it's like, "Hey, it it needs to work." Well, I I love this analogy because I I feel like as a user, my special power is I know how to bend the paper clip to break very quickly. I feel like I should That should be a monetizable service

5:04 that I provide to software companies. But I'm also really struck that um when I I I do hire uh developers uh for different kinds of projects, and that the ability to anticipate when something is going to break is part of how I antici- like is how I evaluate, like how do people handle the fragility of what they're what they're building, and how do they

5:26 detect it. And I guess what I'm curious about is as AI becomes more and more how people navigate the development process, um do you think that we're losing some of those skills around understanding like the user interaction, understanding the um security implications, for example. we

5:49 were talking about that a little bit. I I'm I'm curious about whether you think that people who are kind of essentially growing up and learning um learning the field while these tools are already available, are they missing some of those basics now? Yeah, it's it's an interesting question. I think it it's hard to tell like exactly what the value of those basics are. Like when I was growing up, uh I started programming and we had like this

6:12 little computer at home that cost a few hundred dollars. Yeah. And allowance. And like that the time they sold the like the assembly language assembler for like a hundred dollars. And then there was a C compiler for another hundred dollars that we depended on the assembler. And I could not afford the second hundred dollars. And so I bought the assembler. No way. And I'm like, well, that's that's what's going to happen. I'm going to read the because programs actually came with books at the time. So I read the book

6:34 and I learned assembly language. And so I know how the guts of computers work, right? And then like by the time I'd saved up another hundred dollars, my computer had been obsoleted and like the last copy of the compiler they'd thrown it out at Radio Shack. And I could never get a C compiler. So then we had to switch to long story. But the the point is that I know assembly language. Since that time, I've written almost zero assembly language.

6:57 Right? It's just it's obsolete. Compilers have like eliminated the need to write assembly language. And yet the fact that I learned assembly language gives me a like a leg up on a bunch of people who have like come out since then have never had to write a line of assembly language in their lives. Right? Does that mean those people are obsolete? Does it mean they can't get a good job? Does it mean they can't write good software? Like, no. Right? I can write some software that they can't

7:18 write. But also they can write software that I can't write because they learned something different instead. Mhm. Right? And like the lines of code are just not that important, right? Like stuff you listed about like understanding user needs, right? And reacting to feedback and debugging things and architecting things, like none of that's going away. Like AIs are not doing that stuff for you, especially the user feedback. AIs have no idea what the user experience of your program is.

7:42 And that's like the defining element of engineering. Like what does the user need, right? Does it need to be good? Does it need to be fancy? Does it need to be expensive? Does it need to be cheap? Does it need to scale? Does it need to have a button over here versus over there? The AI can't tell you any of those things, right? And if you're distracted by lines of code, you're not going to think about those things as much as you should. It's It's interesting to hear you say that because one of the things that I

8:06 really struggle with at this point is how how much do you think um folks in those early stages of their career should be investing in Okay, I'm going to say assembly language, maybe not not so much, but you know, in the um nitty-gritty of being able to write a complete program, let's say, what you know, in whatever language, but versus like an a a you know, a young developer

8:31 who maybe has primarily focused on figuring out the requirements and the IA and those sorts of pieces and then is using you know, various AI coding agents to do the I don't want to call it the heavy lifting, but like the rote work, all of the generating of the code. Like if you're hiring a developer or if you're advising somebody who's new in the in the field, are you encouraging them to learn the line-by-line

8:56 code review skills or are you encouraging them to like go manage a team of a hundred virtual coding agents? Well, the funny thing is like all this stuff is valuable skills, right? Like, you know, to this day, if you learn assembly language, there are jobs you can get that nobody else can get because like the people who run these LLMs on GPUs are doing stuff in assembly language to optimize those LLMs on GPUs and train them faster, right? Those are

9:20 very very very high-paying jobs because so few people know how to do them, right? If you want a job that like if you want some skills that'll make it easy to get a job like anywhere, you should probably learn how to train a hundred LLMs or like manage a hundred LLM agents cuz that's what everybody's trying to hire right now. But like both are fine, right? So my advice to people is like if you think it's fun, you should probably learn it cuz

9:41 learning is a skill on its own and the more you learn, the more value you're valuable you're going to be. I know so much random stuff about so many random things. [laughter] And like each day, I'm like, wow, it's surprising that this dumb thing I learned cuz I was interested when I was browsing Wikipedia just paid off in my job as the CEO of Tail Scale. And I just like it occurred to me, it's like, oh, this is like that. I can do it like this, right? And that skill is actually going to be more and

10:04 more valuable cuz like cuz there's going to be weirder and weirder problems. I I mean, I I buy that, but again, I feel like the actual nature of learning is changing so quickly because of AI and how people learn like not just tech technical skills, but any any skill. And I will admit like I do think of this partly as a parent because um

10:26 you know, I have a kid who I thought would be you know, worst case scenario, work from home as a kind of coder by the hour. And those jobs are already gone. Like they're gone now. So, those jobs are not going to be there. So, you know, what what should people invest in learning and what are the like learning strategies that are going to give somebody some longevity as the field of

10:53 um technolo not just I don't I was about to say software development, but it really goes beyond software development as like all of these tech jobs get totally reimagined as AI becomes a bigger and bigger part of the production process. So, the funny thing is like again, I don't I don't know that you need to like over optimize up front, right? If it's something you hate, like I don't think you should force yourself to learn it

11:16 for the most part, right? And because like as the world is progressing, not only is more stuff automated, which is like one thing, but it's it's becoming easier and easier to learn stuff when you need it. Yeah. Right? I got my four-year-old a little stuffed dinosaur. There's a startup in San Francisco that's making these stuffed dinosaurs and it's like an AI stuffed dinosaur, right? And it's fine-tuned for kids. You can like dial your child's age, and it'll talk to them like at that age. But you can ask

11:39 anything you want in the world, and it will it will explain that to you, right? And I didn't have that when I was four, right? But he he asks like difficult stuff, and it can explain it in kids' terms. Like so, if you want to learn assembly language today, you don't have to go through what I did, where like every [laughter] every compile took like 5 minutes, and if you make one typo, it's like, "Whoops, another 5 minutes." Right? Now

12:01 it's like instantaneous. You can ask Claude, "Teach me assembly language, right? Quiz me on assembly language." And you can learn what you need to learn so much faster. So it's so much more important to just like, "Look, be interested in stuff. Learn what you're interested in." Because everybody in the world is like suddenly been up-leveled like two levels, right? Where you weren't a programmer before, like now you're by default. Everybody in the

12:24 world is suddenly a programmer. Just install this thing, and 5 minutes later, you're writing programs. Like that is not obsolete. It's not like you your skills have gone away. But if you know things, you're up-leveled even more, right? The more stuff you know, the more stuff you can do with the same tool. I I I mean, I'm I'm not 100% sold on that, because one of the things that we're observing very quickly is this phenomenon of cognitive offloading, where

12:47 because AI can do these tasks for you, you don't really it it's sort of like a veneer of learning rather than real learning. And again, if you think about that different like those stages of the first job, where maybe you can get by with that versus where you're going to be 10 years into your career, and with the with the hopefully the goal of managing projects

13:10 or managing teams, if you skip over that deeper learning in those earlier stages because AI is kind of answering too quickly, um then you have to make up for it later. And so I'm wondering what you know, what what do people do to challenge themselves in those earlier stages so that even if they're doing kind of the wrote parts of of tech projects, they're building the skills

13:35 that are going to support them over over time. Yeah, I mean I I actually I don't really believe in cognitive offloading as a phenomenon. I think people said the same thing when calculators came out. Like, "No, you need to learn how to do long division on paper." Right? And it's like, you know, I learned that in grade school. I have never once done long division on paper since grade school. And and my my brain has not atrophied, right? But what's what's what's really

13:59 dangerous, the thing that is is truly bad for you, is so-called decision fatigue. Right? And so the danger they talk about this with self-driving cars, right? If you have a self-driving car where you like a supposedly self-driving car where you must keep your hand on the steering wheel because every now and then it's going to make a fatal mistake that would cause an accident and it's your job to prevent that fatal mistake. Right? You're going to be like, "La la la." I'm thinking about something else.

14:21 You're not actually paying attention the way you would be if you were actually driving the car. Yeah. Right? You're only left to be like super hyper alert supposedly for this like one of hundred chance that it's going to screw something up. And you're not going to be paying attention and that's when it gets fatal. And this happens like this can happen if you apply AI to all the supposedly easy stuff or the low-level parts of the job, but you're constantly it's popping up these like

14:44 benign questions. Yeah. Right? And like Claude Code does this when you don't run it in dangerously mode, right? It's like, "Hey, can I do this?" Yes. "Can I do this?" Yes. "Can I do this?" Yes. Here's a 10-line bash script. "Am I allowed to run this?" And I'm like, Yeah. Yes. Right? [laughter] I know. you're not actually making decisions anymore. Now your brain is just like turning to mush. Right? But you don't have to run it that way. Right? What you can do instead is you can have it

15:07 eliminate a bunch of stuff and only bring you the things that are important sometimes, right? But when they come in they're like, "Oh, that's an interesting question. I hadn't thought of that." Right? And that is the opposite of your brain atrophying. It's like, "Oh, that's an interesting question that I I have never even thought of because I was too busy writing lines of code, right? I I'm I So So I totally agree with what you're saying and I also observe that not everybody opts to keep challenging

15:31 themselves. And you know, this is one of the things that I find interesting about, you know, having just written a book about neurodiversity in the workplace and really seeing how um the kind of prototypical programmer brain, you know, people have I mean, I think this has changed, but people used to go into software with a very certain kind of like problem-solving mentality. And so now, you know, you can apply that

15:56 problem-solving to higher order problems. But for folks who were entering the world of software development because it was less secure job and not like an itch at the back of their head, there is that ability to go on autopilot. So, you know, how do you encourage developers, I don't know if we're talking about on your team or people you're talking to, how do you know when you're in autopilot and how do

16:20 you know when you're continuing to challenge yourself? What are some habits you could put in place that ensure that continued growth? Yeah, so one thing I think there's research now that shows this, we saw it in our team as well. Like there's really it turns out there's two kinds of software developers. There's the kind that learns software development cuz they really like typing lines of code into a computer all by themselves in a room for hours at a time. It's really meditative and it is really meditative.

16:42 I love that process, right? Like when I got into coding, I'm like, I love this. It gives me an excuse A not to talk to any people and B I'm doing something useful and it is it's so quiet and I can clear my head and I can get some stuff done. And some people that is the goal is to like have that feeling all day, right? And it's great that you can get paid for it. Um and in the early days of computing like famously people who like people were like, "Huh, I can't believe

17:05 they're paying me to like babysit the mainframe at the university when I would obviously do this for free cuz it's so fun, right?" And then the other kind of person is like, "I just like solving problems, right?" And so the the people who just like meditating at their computer, they are a little bit at risk, right? Like let's be realistic, there's going to be less jobs meditating at the computer because that's actually the thing that isn't using your brain. It's

17:30 meditation is like the opposite of using your brain, right? It's like how do I get the rest of the stuff out of my brain? Stopping and having to ask the like hard questions, like what is the problem that I'm trying to solve and how do I do something useful to solve this problem? Those questions are scary for some people. Now, I found out luckily for me, uh I'm in category two. I just It turned out I just really love solving problems. I actually don't miss typing

17:52 code into a computer at all, right? I thought I would. I thought this was like my whole identity, but it's like, nope. What's really fun is like, oh, I identified a problem, I can create a computer system that will solve this problem and then a whole bunch of people benefit from the thing I created. Like that's awesome, right? But I have to get my meditation somewhere else, right? Like that that part of the job is not there. And I know we have people even at our company that like their identity is,

18:15 you know, this is what I am. I'm a programmer who types code into a computer and I love it. This is being taken away from me. It's like it kind of is. Um and there are there are nevertheless programming jobs that AIs cannot do that you can still do. Uh but it's that's that's where you're a little bit at risk. If there's a specific thing you just love to do over and over again, I don't know. But solving problems is never going to be obsolete.

18:37 It's it's it's a really helpful distinction because I I just had this conversation with a young developer recently who was basically saying, I don't want to do by coding. I like the sitting in the meditative and I was just like, well, I'm I'm sorry you were born 20 years too late for that career. Like I don't even know what to tell young people in that Yeah. What do you do? Do you just

18:59 totally change fields or Yeah, well, I think, you know, getting a little abstract. Like, you know, I still do spend my time quasi meditating. I don't I don't meditate in the official sense of like sitting there and listening to your particular kind of music and folding my legs in a particular way or whatever, [laughter] right? But like sitting there and thinking is is suddenly an extremely valuable skill. Yeah.

19:19 Right? And it's like hard for me as a CEO cuz usually my calendar is filled absolutely to the brim with meetings, but sometimes I just have to clear out meetings for like a week. Yeah. And my job is to sit there and like process all this stuff and like have like one insight. It's like, "Oh, this is the thing that will solve the problem." And the the neat thing now is that like some for for many people that one insight is like, "Okay, now I can bring this to Claud and it can come true

19:43 an hour later, right?" Oh. And before it's like, "Well, I had this great insight. Now I need to build a company to build the thing so I can tell people to set up a team so that they can solve this problem in 6 months or a year, right?" And it's like the the distance from like you can have that meditative state to like I have this brilliant idea that now has come true. It can be like a day. You know, but I mean it's So so

20:06 the the flip side of that as somebody who used to not be able to do all my crazy ideas is now you can do all the crazy ideas. Like because it's so easy to make the thing, it's really easy to make like an endless array of crappy software products. I mean, it brings us back to our paper clips. So again, if the goal is to have developers who are capable of creating and delivering

20:32 actual functioning software that breaks after 20 bends instead of two bends and that actual human beings might want to use and that aren't just like a stick-a-fantic AI's like idea of good software. How do you as a as a developer who's working with your 100 LLMs on a day-to-day basis and not in the guts of the code,

20:54 you know, what do you think are the most fundamental um abilities to cultivate so you have that kind of judgment? So like you know, where do where where do How do engineers become great engineers? Yes, that. Experience. Right? I've been programming for like 40 years. And like I've had to go I've gone through different company or different companies, different teams, different jobs, and like building stuff over like 2 or 3 years, and then after 2

21:18 or 3 years, we finished building it, we send it to the customer, and we find out all the stuff we did wrong. Yeah. Like that's that is a slow learning process. Yeah. Right? The cool thing about LLMs is that the people at Tailscale are doing this right now. I I know this, right? They're like, I want to build this thing. I don't know how. So, I'm going to try 10 different ways of building this thing. Yeah. Right? I'll ask Claude, like give me some ideas for how we might want to build a product like this. And it gives

21:40 you 10 ideas, and I'm like, okay, I'm going to open 10 windows, and I'm going to have Claude build me 10 things. Yeah. Right? And then I'm going to compare to see which one's better. And I just got 10 years of experience in 1 week. Wow. Right? And I've tried all the different things, and I know the pros and cons, and like this is how you become a good engineer is you try stuff, and you see what doesn't work and what does work. Like if you want to experiment with paper clips, I can now try like building

22:04 new kinds of paper clips in a virtual world Yeah. that I never like never could have gotten funding to even experiment with this like way out there method that everybody thinks is going to fail, right? So, when you make things super cheap, like yes, you're going to produce lots of garbage, Yeah. but you can finally do all these experiments and find out which things are surprisingly not garbage, right? One of the worst things about getting old is realizing I actually don't take as many

22:28 risks as I used to when I was 20 because now I know why things are going to fail, Yeah. right? And so, I used to assume they're going to fail, and then I don't do them. And then some startup person who's 20 doesn't know this, and they start a company is like, yeah, well, that would have failed 20 years ago, but the world's different now. That thing you thought was going to fail isn't going to fail, right? And you can find this out so much faster. Like that's how you gain this experience.

22:49 I I really appreciate your perspective. I want to go home and build like 50 pieces of software right away. Um and and thank you so much for sharing with us your perspective on, you know, what it means to be a developer in this world where now the tools are so different for us. Thank you. Yeah, thanks for being here. e.