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Podcast · June 25, 2026

Has the role of an engineering leader changed?

Gregor Ojstersek has built a community of over 200,000 engineering leaders through his Engineering Leadership Newsletter, talking to teams across the globe every day. He has a grounded take on what's actually working right now and what's just noise. In this episode, Gregor and host Emma Webb get into why the best engineering leaders aren't chasing shiny new tools, why the identity shift happening right now is harder than people admit, and why the skills that made you a great engineering manager are exactly the skills AI needs from you.

Transcript

040 —.520 · Speaker 1 Great culture will always be the biggest productivity hack. From 1 to 2 years ago to today, there hasn't been any change in the engineering leadership position. Engineering is serving the business. Business is not serving engineering..520 —.680 · Speaker 2 I think we're at peak token maxing..720 —.

320 · Speaker 1 A personal brand is like, what people think about you when you're not in the room..360 —.280 · Speaker 2 Lead with empathy. Code with curiosity..320 —.600 · Speaker 1 Yeah. We don't know exactly what the titles are going to be in the future, but in general, engineering leaders should be doing what's the best for the team, what's the best for the organization, what's the best for the business..

240 —.200 · Speaker 2 You're listening to We Built What? — the podcast for engineering leaders building in the agentic era. I'm your host, Emma Webb from Augment Code. And today I'm joined by Gregor. Gregor, it's so nice to have you. Thank you for coming..240 —.640 · Speaker 1 Yeah, it's really great to be here..640 —.

300 · Speaker 2 So you write the Engineering Leadership Newsletter. Can you tell me a little bit about how that started?.420 —.780 · Speaker 1 It started a bit more than three and a half years ago. There were no plans with it, it's more or less just me sharing what I know about engineering and engineering leadership, what I learned throughout the years.

But then over time, let's say six months, and after people started to read a lot more, that was kind of like the start. Now it's becoming like a really important part of what I do on a daily basis..780 —.460 · Speaker 2 And you've built this really thriving community of over 200,000 engineering leaders across your Substack and your LinkedIn.

And one thing I'm really curious about is who in your community, who is thriving in this moment, who is like, we're in such a time of change. We're in such a time of everything that we thought was true might not be true in the future. Who is thriving through this moment, and what do they have in common?.500 —.390 · Speaker 1 First of all, I mean everyone.

We are all learning all the time in this era. Nobody has everything figured out, right? Curiosity is a really important skill these days, to kind of like be curious to find out what are the skills that you need to learn in order to be successful. But when I'm talking with different companies and also engineers and engineering leaders across the industry, there's a common denominator in terms of like people hiring for great, great generalists and exceptional specialists.

Great generalists, meaning that they can do work end to end, from an idea to building a product, and own the full spectrum from start to finish. They also have good communication skills, obviously the human-related skills on a good level, like empathy. And they also have a good understanding of many different technology stacks, frameworks, in order to be successful.

And then on the other side, you have great exceptional specialists who, for example, may be really good in a certain rare technology and they have a deep understanding of that particular technology. They can make performance improvements, they can debug really hard issues. They can make sure that everyone is building with best practices in mind.

And those two things I believe are the ones that have the most opportunities these days..630 —.310 · Speaker 2 As you look across your community, what are teams and leaders who are approaching this moment with confidence, with curiosity, with enthusiasm? What are they doing differently in this moment that other people can learn from?.

350 —.580 · Speaker 1 You know, one of the number one misconceptions at this time is that you need to be using either 20 agents, or you need to be using those shiny new AI tools, or you need to be adopting this new technology or this new product. If you're not doing that, you're missing out, right? Fear of missing out is very, very big in everyone, especially when we have a lot of sensationalistic takes across the industry.

They're saying, okay, you need to use this product, you need to use this in this way. But the reality is different, right? It's all about solving business problems. It's all about, you know, making the team better. It's all about doing what is the best for the company. That is what I see the best leaders, the best teams are doing.

They're focusing on how can we provide as much business value as possible? Not, we are going to be adopting like three, four, five, six, seven new shiny tools. We're going to have 20, 30, 40 AI agents working in parallel. The problem is that our mind can't handle the context switching and the cognitive energy that we need in order to actually make sure that all of these agents are productive.

Focusing on building the right things is more important than ever, because we can move faster with coding and building things. It's a lot easier to build these days, but focusing really on what problems to solve. I mean, tools are really important as well, but let's not go overboard. I like to also say that you can't replace a great culture with any of the AI tools.

Great culture will always be the biggest productivity hack for many companies..740 —.500 · Speaker 2 You sound to me like an AI pragmatist, an AI realist, not an AI-in-everything-we-do. Tell me, like, where do you fall just on the AI tool trend in general?.540 —.590 · Speaker 1 Yeah, we see two different spectrums. One is adopting all the AI tools and really saying like, okay, we need to use this tool or we're going to be replaced.

And the other part is not using AI tools at all, right? But I'm kind of in the middle. You know, the problem with going too much overboard on one side is that you're not correct. And it's not the right way to go. And also, of course, every company is different, every organization is different. And what may work for one may not for the other.

I'm always looking from the perspective of what's going to be the best in this scenario, right? And also I lived through the industry shift with, you know, the new JavaScript frameworks. I was kind of like leaning always toward the new shiny thing. I was trying to learn new things all the time. But what this taught me is that the new thing is not always better.

The same thing is with AI tools. Pick a certain tool that helps you, pick a certain tool that is going to make you more productive. But don't try to change your tooling like every day, every two days, completely change your stack because you see a certain X post or a certain LinkedIn post that is promoting a certain new product.

Always work on what's going to be the best in your case..630 —.230 · Speaker 2 So we're recording here in San Francisco. We are in the heart of AI land, the heart of the bubble. You probably noticed when you came in from the airport. You're based in Slovenia. You have a very global community. Do you notice that kind of difference in opinion or the difference in mindset?

Tell me about kind of just your perspective on how engineering teams that are differently located geographically are thinking about this. What's your observation?.390 —.530 · Speaker 1 The companies here are very prone toward making fast decisions, making fast changes, trying out new things, while in Europe it's a lot more prone toward stability and making sure that we have long-term success, because many people will be reluctant to make a change.

So that is the first thing. The second thing I would say is risk taking. In European companies, there is a lot less incentive to do that. In the United States, especially in San Francisco, it's a lot easier to raise funding. So once you have more funding, you are able to take more risks in general and be able to make changes faster..

690 —.730 · Speaker 2 Some clear differences. Sounds like you think there's maybe a happy medium that we could hit somewhere in between those..770 —.570 · Speaker 1 The balanced part is the best way to go. And also, you know, it's great to have different cultures inside an organization, because you need diversity. Because if there are too many people that are the same, you lose on that creativity.

And also, people cannot learn as much from each other..570 —.970 · Speaker 2 So you mentioned that you started your community about three years ago, really focused on that transition that a senior technical IC engineer is going to have where they want to get into the management, the leadership level. Three years ago, I definitely see why that makes a ton of sense.

Does that transition still make sense today? Do we still have demand for those engineering managers in this world?.970 —.160 · Speaker 1 We see the trend of a lot of engineering managers and engineering leaders becoming ICs. The way I look at engineering leadership is not management versus IC. I always looked at staff engineers and beyond, because they are more focusing on organizational challenges and less on just their own individual contribution.

This hasn't really changed as much, but what I do see — a really, really important trend — is a lot of engineering managers go back to being ICs, and they are sought after because they have a lot of the skills that you need in order to thrive in the AI era. For example, in order to do AI-assisted engineering well, you need to be good at delegating things.

You need to be good at managing the context. You need to be good at dissecting the bigger tasks into smaller tasks. You need to be patient with AI agents. You need to make sure you give proper feedback and things like that. And all of the skills that you learn is basically what engineering managers have been doing. Directors of engineering, VPs of engineering have been doing.

So those kind of people that have like a builder mentality, that can also build things and own things and have good engineering fundamentals — there's always going to be a place for people who are going to make things better..200 —.540 · Speaker 2 Yeah. Being an engineering leader isn't about being a manager. It's about true leadership skills, and those are more important than ever.

That makes a ton of sense. You know, speaking of that, though, like what do you think has changed in the engineering leader role in the past few years? It's been a pretty tumultuous and turbulent time. Is there something that you think was less important and is now very important, or vice versa? Like, what would you say if you look broadly, even from the level of like a role description or how you think about leadership — what's different now?.

620 —.230 · Speaker 1 Yeah, I'm going to give a bit of a controversial opinion here, which is basically, from 1 to 2 years ago to today, there hasn't been any change in the engineering leadership position. And the reason why I'm saying that is that engineering leaders should be doing what's the best for the business, for the team, for the organization, for the people.

Right? So that, on the high level, hasn't really changed. The only change that has been was basically the focus, the tools, you know, the processes, everything around what we should be doing, right? But the overall mentality and the high-level mindset that great engineering leaders have been incorporating hasn't really changed.

As you mentioned before, title is just a title. The mindset and the attitude of the engineers is very, very important. But I like to put it as two different distinctions, which is human-related skills and problem-solving abilities. Right? Those two areas are more important than ever. It's not, you know, about being really good in a certain technology, because you need to be more technology-agnostic these days.

Going back to human-related skills, like communication. Empathy is very crucial in terms of understanding the customers, understanding your team as well, what the team needs. Of course, business understanding, product understanding is really important and more important than ever. On the problem-solving abilities — you know, being resourceful, being able to talk with other people about what they're using, what they're building, what tools are they using, having a good network of people.

Like, for example, the event that we are doing is exactly what we need in our industry, which is so that engineering leaders can talk with each other and see how we can help each other and how we can, you know, utilize the knowledge of each other and use that in our organizations. With organizations, there's a lot of hidden rules and unspoken motivations behind different things.

Like, for example, a certain executive might have a motivation to do this, but AI doesn't understand that. Right? But you, you as an engineering leader, you have that pragmatic view of everything, that you see all of those hidden insights. And you can manage those expectations the right way..270 —.330 · Speaker 2 The hidden skills that you need in an organization is really fascinating to me.

And I think it's really fascinating to me because if you think about engineering, it's often, you know, it's very linear. It can be, you know, this happens and this, and in this order. And in an organization there is, to your point, so much that's unspoken. One of the things that I think about a lot is, as a leader — this may be my hot take, but I think the most important skill is to be able to think through what is the information that different groups of people need to know, and in what order do they need to know it to be successful?

Like, who do I need to tell what when, so that they're motivated to go do the thing? And that is not something I think you can teach AI. But maybe I'm wrong..370 —.760 · Speaker 1 No, no, you're completely right. Those are kind of things that you need a pragmatic approach and also like a human touch in order to do it. A really good similar example is building a narrative around your work, because what I like to say is you can do the best work in the world, but if it's not aligned with the expectations, it's not going to be perceived that way.

And a lot of engineers are thinking that the emotional aspect is not important, but the emotional aspect is crucial. In terms of like, okay, we are doing this amazing work — how can we make sure that everyone is going to perceive this to be amazing work? And it's all about building kind of like a good narrative behind it, and you can only do that with a good human touch.

And also kind of like having a good feel for people, and what is the appropriate thing to say. Reading the room is a really important skill for engineers and engineering leaders. So when you're speaking with executives, you're speaking more in terms of like business, and their motivations. When you're speaking with engineers, you're speaking more in technology terms.

But it's a really important distinction to make, because if you're just going to speak in technology about, okay, this framework, this AI agent and so on with other executives, they're going to be like, okay, we don't really trust what they're doing because we can't understand what actually they're doing. But if you speak in a way that, okay, if you do this project, we're going to increase the revenue by this amount of percentage, we're going to increase the daily active users by this amount of percentage — that's automatically going to be perceived from other leaders across the organization a lot differently..

800 —.100 · Speaker 2 I think to the point about those generalist skills are so important. I think when you first said that, I was thinking about kind of generalist engineering, generalist technology skills, and now I'm thinking, no, it's actually like generalist business skills. Like, do I really understand the shape of this business?

Do I really understand how it operates, why it operates, what's important? And that piece, I think, has — because the engineering, the technology part has been so consuming and so difficult, hasn't been as top of mind, I think, for some folks. But now, because of the speed at which we can build and operate, is even more critical.

If you can't articulate the context of the shape of like what you're in, how do you possibly build the right thing when we could build anything so quickly?.140 —.550 · Speaker 1 Exactly. It's all about articulating the requirements. What I like to say is what we're building is a lot more important these days because we can move faster.

And if you can frame the problems the right way, if you can think about what are the business problems that you're trying to solve, the customer's problems. And you can create like a spec — spec-driven development is a really kind of like a good standard these days that a lot of teams are focusing on. You can really solve a lot of problems ahead of time.

And if you create a great specification before you start developing, you're going to be, you know, really close to actually providing AI a really good platform to create the generated code that is needed. Of course, the important part is also setting the right architecture, setting the right systems. Those are all very important and so on.

But framing the problems and understanding what needs to be built is more important than ever. And of course, being able to work with cross-functional people from the other departments — especially crucial skills for engineering leaders. And what I'm also going to say is, also a really extremely important topic is managing expectations, especially these days.

A lot of leaders across the company have — of course, we talked about fear of missing out — they're seeing a certain, you know, post on certain social media or certain video about this tool is going to be the best in the world, and then it's automatically, okay, why are we not utilizing this tool? And then it falls down to engineering leaders and engineers to be able to manage those expectations.

So you need to be extremely, extremely good in building a really great relationship with other executive, more type of folks, and also being able to articulate what are the pros and cons of certain tools. And also you need to position yourself in a way that you're going to be an authority on this field. That's also why my recommendation to a lot of engineering leaders these days is to write online.

Public speaking is very important, and you need to make sure that you are put in a position to be an authority on this field. If you're not, the problematic part is going to be that you might not even get invited to the room to speak about AI adoption — but you need to be the one who is driving the adoption across the company..

590 —.330 · Speaker 2 Yeah. I was going to ask you about the kind of personal brand building for engineers, because I don't think that was your goal when you started the community. But definitely, you know, it has been, I would say, a side effect of all of the writing and speaking and kind of community building that you've done.

I find even working with our own engineers, some of them are super excited to tell me about what they're building and to do talks and things like that. And some people are like, please leave me alone. I'm busy. I don't have time for this. How do you kind of tell the story about why that piece is important? Yeah, what should I tell the folks who are like, Emma, I don't want to write a LinkedIn post?.

370 —.260 · Speaker 1 Yeah. You know, more important than ever, especially for engineering leaders, you need to be a role model for others. The expectation is, the more you grow in your career, the more you're expected to also attract talent and also retain talent. That's also where personal branding comes in. It's very important.

I'll give you a good example from my experience. When I was a full-time CTO, I started as a VP of engineering, and then after six months, I got asked if I wanted to become a CTO. And one of the reasons was basically writing online and building a personal brand and building that social presence, social proof. Because, you know, we are still human, and we value what others are saying about certain people, right?

And, you know, I found out, especially when I was getting a lot more traction with my writing and what I'm sharing that people find to be interesting — it was a lot easier for me to get buy-in on certain ideas, certain approaches, certain tools, certain directions than before. And also, people trusted me a lot more in what I'm saying, what kind of decisions I'm making.

And also my team were a lot more happy to be a part of the team, to be working, and so on. It all kind of connects together, right? Especially these days, it's important to be able to influence, especially across the business. What I like to say is a personal brand is like what people think about you when you're not in the room.

It's not what I'm focusing on. You know, I focus on sharing what is going to be valuable for engineers and engineering leaders, and also what I'm learning personally, what I want to learn as well. But at the same time, this helps me to be able to, you know, say things to certain engineering leaders, to certain company leaders, and they will take it a lot differently than maybe some other people who are not sharing so publicly about, you know, what they're learning and things like that..

260 —.820 · Speaker 2 I wonder about this, and you can tell me if this is right or wrong, but I think because AI is such a hot topic, I imagine engineering leaders are getting a lot more questions about technology from non-technical folks than they ever have before, where people are really trying to dive in and be like, oh, are you using this or that tool?

But what underlying model, what have we thought about, building this way? And you're like, you never asked me that before. Like, why are you in the — why are you in the how? You know what I mean? Like, kind of get out of here. But I feel like that attitude maybe is not going to help people be productive in the long run either.

You know, if you have your peers or your leadership coming in and saying, Gregor, have you tried this new workflow tool? It's going to change your life. And you're like, come on..860 —.100 · Speaker 1 Yeah..140 —.810 · Speaker 2 You know, it's hard to like avoid that initial reaction that's like, please stop bugging me about AI.

Does that make—.810 —.630 · Speaker 1 Sense? Definitely, definitely makes sense. But what I suggest to engineers is to embrace the feedback, because a lot of people who are outside of the field, outside of engineering, have a lot of creative ideas and a lot of the kind of like out-of-the-box thinking, because a lot of us engineers, we are in the box.

Right? And we think from what we see and what we are working on on a daily basis. But a lot of people outside, let's say from HR, from finance, from marketing, from all the other departments, they have a lot of creative ideas and they have a lot of potential problems that they can solve with AI. Right. So it's really important for you to be a good listener and kind of like get the feedback the right way.

And you can get the feedback via forms, and then you can use AI to actually digest that feedback the right way. But it's important not to be that dismissive as well, because every opinion is very valuable. And at the same time, you as an engineering leader — it's not only how you can help your team and how you can help the engineering department, but also how can you help the other departments.

The important thing I like to say is engineering is serving the business. Business is not serving engineering. Yeah. So how can we make sure that the business is going to be successful, that the organization is going to be successful, that other departments are going to be able to do things better? When you're framing things like that, it's a lot more inclusive.

It's a lot more different mindset. And people are going to view you a lot more differently, because you're trying to solve their problems, not only focusing on your problems. Right. That is more important than ever, I believe..670 —.430 · Speaker 2 It's cool too, because the underlying technology, with all of the foundation models, with all of the tools, is changing so quickly that someone who's non-technical might come and be like, can we do it this way?

And you're like, well, I don't know. Maybe — like, we don't really know. It's like moving so fast. Let's go find out. We can explore together. So that's kind of a fun, creative moment that we're in as well..470 —.620 · Speaker 1 Let's do a quick proof of concept and let's try it and see how it works. Nobody really has all the answers right at this time.

It's all about how can we try it out as fast as we can, so we have the answers in order to build it the right way..660 —.620 · Speaker 2 We recently went out and surveyed a bunch of engineering leaders in our community at Augment, and one of the things that we found out was that there's no shared definition of AI native.

What does being an AI-native engineering team or an AI-native leader mean to you?.700 —.580 · Speaker 1 What AI native means is totally different from one company, one organization, to another, right? In some cases, companies, you know, you need to use 500K a month AI tokens per engineer, right?.060 —.780 · Speaker 1 Yeah, exactly.

You need to be token maxing..980 —.740 · Speaker 2 I don't think that's going to persist. I think we're at peak token maxing, and it's gonna—.780 —.360 · Speaker 1 Yeah. The problem with this is that the AI tokens are going to get just more expensive as time goes on. And then it's becoming more and more important to be able to minimize the token spend as much as possible.

And we can see a lot of companies are already focusing on building things in order to decrease the amount of tokens that companies are spending. It's all about solving the problems that your team, the organization, and the business have, right? And utilizing the tools, let's say AI tools, in order to do that. And it's all about, you know, how can we continuously improve the way we work, the way the processes are.

Nothing really is sacred — like the process that we have right now, it should be continuously improved and get better. We should always look to kind of reinvent the way we work. Also, you know, if you see that something is not working, let's remove that. It's no big deal if some AI tool is not working. Okay, let's not use that anymore..

400 —.640 · Speaker 2 Gregor, anything you wanted to talk about, or that I should have asked you that I didn't?.680 —.990 · Speaker 1 One important message I want to say is, you know, nobody has all the answers at this time. The shift is quite hard for many people because of the identity shift that you need to make. A lot of engineers have been identifying themselves with certain tools, with certain frameworks, like for example, being a Rust developer, being a JavaScript developer, being a React developer.

That is less important these days, and it's more about you being able to solve problems, rather than identifying with a certain bit of a certain framework or technology. The sooner you accept that, the better it's going to be. But I can really see how emotional this shift can be. My recommendation is, you know, evolve as time goes on.

See what's really important. Don't be too much into what's been working for you in the last five years, last ten years. Continuously evolve and see what's going to be beneficial for the team..030 —.150 · Speaker 2 Lead with empathy. Code with curiosity. Yeah, exactly. Exactly. Awesome. Well, thank you so much for joining.

This has been such a pleasure and delight to talk to you. I've learned so much, and I can't wait for other people to hear this too..190 —.550 · Speaker 1 Thank you. Thank you for having me..590 —.030 · Speaker 2 You've been listening to We Built What? If you liked what you heard today, please like and subscribe. Share with a friend.

Share with an agent. If there's someone you think we should talk to, reach out and let us know on LinkedIn or X.

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