In this episode of the groCTO Podcast, host Kovid Batra is joined by Ben Matthews, Senior Director of Engineering at Stack Overflow, with over 20 years of experience in engineering and leadership.
Ben shares his career journey from QA to engineering leadership, shedding light on the importance of creating organizations that function collaboratively rather than just executing tasks independently. He underscores the need for cross-functional teamwork and reducing friction points to build cohesive and successful teams. Ben also addresses the challenges and opportunities presented by the AI revolution, emphasizing Stack Overflow’s strategy to embrace and leverage AI innovations. Additionally, he offers valuable advice for onboarding junior developers, such as involving them in code reviews and emphasizing documentation.
Throughout the discussion, Ben highlights essential leadership principles like advocating for oneself and one’s team, managing team dynamics, and setting clear expectations. He provides practical tips for engineering managers on creating value, addressing organizational weaknesses, and fostering a supportive environment for continuous growth and learning. The episode wraps up with Ben sharing his thoughts on maintaining a vision and connecting it with new technological developments.
Kovid Batra: Hi, everyone. This is Kovid, back with another episode of groCTO podcast. And today with us, we have an exciting guest. This is Senior Director from Stack Overflow with 20 plus years of experience in engineering and leadership, Ben Matthews. Hey, Ben.
Ben Matthews: Thanks for having me. I just wanted to cover you there.
Kovid Batra: All right. So I think, uh, today, uh, we’re going to talk about, uh, Ben’s journey and how he moved from a QA to an engineering leadership position at Stack Overflow. And here we are like primarily interested in knowing how they are scaling tech and teams at Stack Overflow. So we are totally excited about this episode, man. But before we jump on to the main section, uh, there is a small ritual that we have. So you have to introduce yourself that your LinkedIn profile doesn’t tell you about.
Ben Matthews: Okay. Uh, well, that’s not in my LinkedIn profile. Well, um, So I am the Senior Director of Engineering at Stack Overflow for our community products, but something about myself that’s not, uh, I, I love to snowboard. I’m a huge fan of calzones and I’m a total movie nerd. Is that what you had in mind?
Kovid Batra: Yeah, of course. I mean, uh, I would love you to talk a little more, even if there is something that you want to share that tells about you in terms of who you are. Maybe something from your childhood, from your teenage, anything, anything of that sort that you think defines you who you are today.
Ben Matthews: Uh, yeah. Um, yeah, that’s a great question. Of, of really just getting into tech in general, a lot of that did come from some natural inclinations, uh, that have kind of always been there. For the longest time I didn’t think I would really enjoy technology. There was the stereotype of the person who sat in the corner, just coded all day and never talked to people like kind of the Hollywood impression of what a developer was. That didn’t seem very appealing. I like interacting with people. I like actually making some tangible differences, but once I actually dug into it and actually saw like there was that click that a lot of people have the first time that you compile and run your code and you’re like, wait, I made that happen. I made that change and that’s what kind of the addiction started. But even after that, I still loved interacting with people. Um, and I think we were very lucky. I came at a time where the industry was starting to change, where it was no longer people working in isolation. This, this is a team sport now, like developers have to work together. You’re working with other departments. And that’s actually kind of what I really enjoy. I love, I love interacting with people and building things that people like to work with. So, um, that’s really kind of what sings to me about tech is it’s a quick way to build things that other people can interact with and bring value to them. And I get to do it together with another team of people who, who enjoy it as well. So I would say like, that’s kind of what gets me out of bed in the morning of trying to help people do more with their day and build something that helped them.
Kovid Batra: Great, great. Thanks for that intro. Um, I think, uh, I’m really interested to start with the part, uh, with your current role and responsibility at Stack Overflow. Uh, like, uh, like how, uh, you, you started here or in fact, like, we can go a little back also, like from where you actually started. So wherever you are comfortable, like, uh, you can just begin. Yeah.
Ben Matthews: Yeah. Um, so the, the full journey has its interesting and boring parts altogether, but how it really started was out of school, I still had that feeling of I didn’t know if development was for me because of the perception I had. But I actually got my first job as a quality assurance engineer for a small startup. Uh, now the best part about working at a small company is that you’re forced to wear multiple hats. That, you know, you don’t just have one role. I was also doing tech support. And then I also looked at some of the code. I helped to do some small code reviews. And from there, I thought like, you know, I would love to take a shot at doing this development thing. Maybe, maybe I would like it more. Um, and then I did, I kind of got that high of like, I pushed this live and people are using it and you know, that’s mine and they’re enjoying it and that kind of became addictive to me, of where I really liked being a developer. So I really leaned into that. Um, and then enjoying that startup and having a great mentor there, uh, that really kind of, I set a foundation for how I view, how I want to develop and the things I want to build, uh, of really taking the point of view of how I’m creating value for the users. And my, and my next role, I actually worked for a marketing agency doing digital marketing. Um, and that took that up to 11 of the number of things I had to interact with and be prepared for. Like every week or every couple weeks I had a new project, a new customer, a new problem to solve, and I had to use usually with code, sometimes not with code. We’re solving these problems and creating value and getting that whole high level view of working on databases, kind of doing QA for other people doing development front and back, and I got to see what I really like to do. But I also got an insight into how organizations work, how pieces of a company work together, pieces of a development team work together, and how that really creates value for, for users and customers, which in the end, that’s what we’re here to do is to create value for people.
Um, so my next role after that is my first foray into leadership. I went to another digital agency leading a small development team. And, um, it had its highs and lows. There was definitely a learning curve there. Um, there, there was that ache of not being able to develop of, of enabling other people to develop.
Kovid Batra: Yeah. And this was, and this was a startup or this was an organization like, uh, medium or large-scale organization?
Ben Matthews: This was a medium-sized organization, much more, uh, founded, they, they were trying to start up a new tech department, so I had a little freedom in setting some standards. But it was a mature organization. Um, they kind of knew what they wanted to accomplish. Um, so like then I had a big learning curve, excuse me, of what it’s like to work there, how do I lead people, how do I set expectations for them, um, how do I advocate for myself and others, and, you know, I had plenty of missteps that like looking back now, there’s a bunch of times I wish I could go back and say, “Nope, this is totally the wrong direction. Your instincts are wrong. You need to learn and grow.” Um, and then after that I went to a couple of other organizations of doing leadership there, some very, very large, some smaller, getting that whole view of kind of ins and outs and the stacks of what I would like to be. Then I landed here on Stack which has been a terrific fit for me of, of getting to work directly with users and, uh, and knowing that the people I’m leading are customers, of Stack Overflow just as much as they are employees here, which is very satisfying. We really feel like we’re helping people. I get to have a big impact on a very large application and, um, there’s still a lot of freedom for me to, to execute in the vision. Working with the other leaders here has been a joy as well, since we’re kind of like-minded, which I think is very important for people looking for a place to land. Uh, I know in a lot of interviews, you rarely get to interact with people who will be your peers, but when you do, like really see how well do you bounce off of each other, um, are you all alike? Cause that’s not great. Or are you all different? That’s not great either. You want to have like a little bit of friction there so you can create great ideas. And I think that’s what we have at Stack and it’s been wonderful.
Kovid Batra: No, I think that’s great. But, uh, one question here. Like, um, you were very, uh, passionate about when you told how you started your journey, uh, with the, with the startup, you got an exposure, uh, from the business level to, uh, product teams to developers, and that really opened your mind. Um, would you recommend this for anyone who is beginning their journey in, in, in tech, like, uh, would this be a recommended way of going about how you, uh, set your foundation?
Ben Matthews: Yeah, that’s a great question. I think a lot of people are going to have very different journeys. Um, that I think, you know, one thing that really stuck out to me actually just recently talking to someone when I was, I was at a panel just this past weekend and the variety of journeys that people took of where they started. I think one of the most fascinating ones was someone who was not in tech at all. They’ve been a teacher for 15 years, teaching parts of computer science and design, never professionally worked on one. And now they’re breaking into it now and having a lot of success. Um, I mean, I think my advice to people is like, like your journey is not right or wrong, whatever you’re trying to get to, I think there’s plenty of ways to get to it. What I would say that you do want to focus on though, is that you keep challenging yourself of what I thought I would be working on now is certainly not, uh, what I’m actually working on today, uh, even, whether, I think that’s at all levels, whether at senior, uh, executive, down to like junior engineer, uh, from year to year, the technology landscape changes. How we organize people and execute on that changes. Um, so whatever that journey is, whatever you think it’s going to be, I’m 99 percent sure it’s going to be different than what you envisioned and you have to be prepared to shift that way and keep learning and challenging yourself and it’ll be uncomfortable but that, that’s part of the journey.
Kovid Batra: Yeah, I think that’s the way to go, actually. Then that’s the area when you learn the maximum I think. Uh, so yeah, totally agree with that. Uh, when, uh, when you reflect back, when you see your journey from a QA to a Senior Director at Stack Overflow, I’m curious to know, like, do you know what is that quality in you, uh, that made you stand out and grow to such a profile in, in a, in a reputed organization?
Ben Matthews: Yeah, I think, um, I had a great mentor that pointed out a lot of things that weren’t obvious to me. Um, and I think being a developer, um, I think sometimes for, for us being a people leader is it doesn’t come as naturally sometimes because we tend to think more functionally, which isn’t a bad thing. But there’s some things that at least for me, it didn’t jump out, obviously. I remember one great piece of feedback that took me from just a team manager to get me into a higher level piece was really advocating for yourself. Uh, that didn’t come naturally to me. And I don’t think that comes naturally to a lot of people in our industry. Um, some like to just label it as bragging or see it as bragging, but if you’re not being proud of your successes, other people won’t know they’re there. But it’s not even just for you, but you should be bragging and, and communicating the successes of your team, communicating the successes of your organization. That’s a big part of letting people know of what’s worked, what hasn’t. So one that you can keep doing it. But also other people can emulate it, emulate it and other people in your organization can see you there. There needs to be a profile there. You need to be visible to be a leader. Uh, and I separate that from manager. Being a manager, you don’t necessarily have to be visible. You, there’s very good managers that don’t like to be in the limelight. They’re still supporting their people and moving things forward. But if you’re going to be a leader and set an example and set hard expectations of the vision of where things are going to go, you need to be visible and part of that is advocating and communicating more broadly.
Kovid Batra: Sure. Makes sense. Okay, coming back to your, your current, uh, roles and responsibilities at Stack Overflow. I’m sure working with developers, uh, who know, uh, what the product is about and they are themselves the users. What is that, uh, one thing that you really, uh, abide by as a principle for leading your teams? How, how you’re leading it differently at Stack Overflow, making things successful, scalable, robust?
Ben Matthews: Yeah. Um, and that’s a great question. Cause every organization is different, I’ve had to tackle this problem in different ways at different places. At Stack, I’ve been very fortunate that, uh, there’s already a very talented group of people here that I’ve been able to expand on and keep growing. Um, people tend to be very passionate about the project already, the project and products that we build. That’s a great benefit to have as well. You’re not really trying to talk people into the vision of Stack Overflow, that they were users before there were customers. So that, that was great. But, um, but with that also comes like a different way of how do you leverage the most out of people given this hand? Um, and I know it’s partially a cliché, but with that vision that’s already there with already talented people, um, kind of the steps of making sure you’re setting clear expectations for your folks, setting that vision very loudly, broadly, and clearly to them, um, and then making sure they have all the resources they need to do that. Sometimes it’s time, sometimes it’s, it’s some money or equipment. And then lastly, kind of getting out of their way and removing all the roadblocks. Those three steps are kind of the big parts that I think are general rule of thumb, but, um, given that a lot of other friction points were out of the way, I could really lean into that.
A great example was, uh, I had a team that, uh, was trying to work on a brand new product that, uh, no, it didn’t quite work out before, but we were going to give it another try. We were starting over. And looking at some of the things that went well and what didn’t, it was honestly just a clear lack of vision was their problem. They kept changing directions often. And I was talking to product of like, “Hey, what went wrong?” And they had their own internal struggles. We had our struggles and just aligning that saying like, “Hey, this is going to be a little bit more broad. We’re specifically trying to accomplish this. How do we do it?” And from a bottom-up approach, they set the goals, they set what they think the milestone should be, and that was so much more successful. Um, like that formula that doesn’t work everywhere, but it really thrives here at Stack of like, “Hey, what do you think? How is the best way to execute this?” And we tweak it, we manage it, we keep it on the rails. But once they started moving into it, um, it actually launched and became very successful. So that’s another way of like, kind of reading your team, reading the other stakeholders and, and leveraging their strengths.
Kovid Batra: But what I feel is that, uh, it’s great. Like this approach works at, uh, Stack, but usually what I felt is that when you go with the bottom-up approach, uh, there is an imbalance, uh, like developers are usually inclined towards taking care of the infra, managing the tech debt and not really intuitively prioritizing your, uh, customer needs and requirements, even though they relate to it at times, at least in case of Stack, I can say that. But still there is a, there is a bias in the developer to make the code better before looking at the customer side of it. So how, how do you take care of that?
Ben Matthews: That’s a, that’s a great point. Um, and just to be clear to other developers listening, I love that instinct if you have it, it’s so valuable that you want to leave code better than you found it. But, uh, to what your point, I think that goes back to setting those clear expectations again of, “Hey, like this is what we’re going to accomplish. This is how we need to do it. Um, if we can address tech debt along the way, you need to justify that. I give you the freedom to justify that. But in the end, I, I’m setting these goals. This is what has to happen by then and I’m happy to support you and what we need to get there.” Um, and then also sharing advice and, and, and you know, learning where the minds are on some of those paths. Uh, some people have experience in making these mistakes like I have. I’ve, uh, tried to say, “Well, we could also do this and then also do this and then also do our goal.” And then we’ve taken on too much, and we’re, you know, we’re trying to do too many things at once that we can’t execute.
So you’re right in that. Just kind of not giving any clear direction or expectations, things can kind of go off the rails and what they want to work on isn’t always what we need to focus on. I think there’s a balance there. But, uh, yeah, I mean, setting those expectations is a key part to those three steps, I would say arguably the most important part. If they don’t know which way they’re supposed to be aiming for, they can’t execute on it.
Kovid Batra: Makes sense. Okay, um, next thing that I want to know is, uh, in the last few, few, not actually, actually few years, it’s just been a year or two when the AI wave has like taken over the industry, right? And everyone’s rushing. Um, I’m sure there was a huge impact on the user base, but maybe I’m wrong, on the user base of Stack because people go there to see code, uh, libraries and like code which is there. Now, uh, ChatGPT and tools like that are really helping developers do like automated code. Uh, how you have, uh, taken up with that and what’s your new strategy? I mean, of course you can say everything here, but I would love to know, like how it has been absorbed in the team now.
Ben Matthews: Now, um, I think for the most part, we’ve kind of worn our strategy on our sleeve. Our, our CEO and Chief Product Officer and our CTO have talked about this a bit of, I mean, Stack is, is there to help educate and empower technologists of the world. This is a new tool that’s part of the landscape now and there are a lot of companies that are concerned about it or feel like it’s a doomsday. Um, we’re embracing it. It’s a new way for information to get in and out of people’s hands. Uh, and this is something we were going to try to be a part of. I think we’ve made some great steps of leveraging AI, uh, we’re trying to build some partnerships with people to kind of get a hand on the wheel to make sure that like this is going in the right direction. But, um, there’s technical revolutions every couple years, and this is another one. Uh, and how Stack fits into it is we’re still going to try to provide that value to folks and AI is a new part of it. Uh, we’re building new products that leverage AI. Um, we actually have a couple that are hopefully going to be launching soon that try to improve the experience for users on the site, leveraging AI. We’re going to try to find new ways for people to interact with AI to know that Stack Overflow is a part of what that experience is and to kind of create a cycle there. Um, But it’s changed how people work. But I think Stack Overflow is still a big part of that equation. Uh, we are a big knowledge repository, uh, like along with Reddit or, or news articles, like all of these things need to be there to even power AI. That, that’s sort of the cycle. Like, um, that has to go there. Without human beings, without a community generating content, AI is pretty powerless. But, um, so there has to be a way for us to keep that feedback loop going. And we’re excited that of all the opportunities to be a part of that and find new ways to keep educating people.
Kovid Batra: Definitely. I think that’s a very good point, actually. Like, without humans feeding that information, at least right now AI is not at that stage that it can generate things on its own. It’s the community that would always be driving things at the end. So I also believe in that fact. My question, uh, a follow-up question on that is that when such kind of, uh, big changes happen, how, how your teams are taking it? Like, at Stack, how people are embracing it, particularly developers? I’m just saying that if there are new products that we are going to work on or new tech that we are going to build, how people are embracing it, how fast they are adopting to the new requirements and the new thought process which the company’s adopting?
Ben Matthews: Uh, through the context of AI or just in general?
Kovid Batra: Just, just in the context of AI.
Ben Matthews: Oh yeah. Um, well, in a fun way, there’s been a wide range of opinions on how for us to embrace or to try to channel the AI capabilities that are now very pervasive in the industry. Um, um, so first part of it starts with a lot of that we’re trying to gather as much data and information we can. Again, we have a good user base. So we’re able to interact with them and ask them questions. We’re looking at behavior changes. And so from there, we try to make a data informed decision to our teams of like, “Hey, this is what we’re seeing. So this is what we’re going to try.” Um, I mean, the beauty of data is there’s a bunch of ways to interpret it and our developers are no different. They have some thoughts on, on the best ways to go about it. But I think this also goes to a general leadership technique is you’re never going to get unanimous consent on an idea. If that’s what your requirement is, you’re never going to move forward. What you do have to get is people to at least agree that this is worth trying or like understand that I might be wrong. And a lot of people feel like this is the best way, so we’ll give it a shot. Uh, and that’s something I’ve been proud of to be able to achieve at Stack. It’s something that is very important for a leader of saying, “Hey, I know you don’t agree, but I need you to roll along with me on this. I understand your point. You’ve been heard, but this is the decision we’re making.” Um, a lot of people agree with the idea. Some don’t, but trying to get the enthusiasm and I think also connecting the dots on those ideas with the larger picture. I think that’s also something people miss a lot during these revolutions of if you start out with like vision A. And then something big happens and now you have vision B, um, you still have to connect the dots in like, “Hey, we’re still trying to, to like provide value the same way. We’re still the same company. We’re in this new thing that you’re doing. This dot still connects to what we want to do. There’s still a path there. We’re not like totally pivoting to block chain or something like that. It’s not a huge change for us.” So I think that also motivates people like we’re still trying to build the same vision, the same power for the company. We’re just doing it in a different way. And what you’re doing is still really creating value. I think that’s a big part for leaders to, to keep people motivated.
Kovid Batra: Makes sense. When it comes to, uh, bringing developers on board and nurturing them, I think the biggest challenge that I have always heard from managers, particularly is, uh, getting these new-age, uh, junior developers and the fresh ones coming into the picture. Um, any thoughts, any techniques that you have used to, uh, bring these people on board, nurture them well, and so that they can contribute and create that impact?
Ben Matthews: Yeah. Uh, onboarding people is a huge thing that I try to give the other managers that work for me that are bringing on new team members. Um, uh, I mean, a big part of it, it goes back to empowerment, but I think a lot of it is also the same challenges we’ve had I think for decades, of me even having my own Computer Science degree. In my first development job, there was a huge gap of what I learned in school versus what I’m doing day-to-day as an actual developer. Uh, as far as I can tell, that hasn’t really changed that much. People come in from bootcamps or not. Uh, funny we’ve had a really good experience of people that don’t have formal degrees coming in, who have just been coding their whole time. They tend to actually have an easier time working within a team. That’s not to disparage any Computer Science degree, it’s still very valuable, but it’s just to highlight the gap between what you actually do and what they’ve been training. A great example is, um, of what we try to get junior engineers to really focus on initially, it’s like just doing code reviews. That is a huge part of what we do in modern development. It’s a great way for you to understand the code base, understand how your team works, understand like kind of the ins and outs and where some of the scary parts of the code are. And, um, and even though that can be intimidating, the best thing I think you can do in a code review is just ask questions of like, “Hey, I see you’re doing this. This doesn’t make sense to me. Can you explain why?” And after time, even a senior engineer will read them and be like, “You know what? That is kind of confusing. Why did we do it that way? Let me..” And they’ll even update their PR. I think that’s one of the best tools to get a junior engineer up to speed is just like get them in the code and reviewing it.
Um, the other part of kind of the unsung hero of all of software development that never gets enough love is just documentation, of having them go through some of the pieces of the product, commenting and documenting how things work. That, one, it helps onboard other people, but two, that, that forces them to have an understanding of how parts of the code work. Uh, and then from there at their own pace, here at Stack, we, we try to have people push code to production on day one. Uh, we find something small for them to do, work them through the whole build pipeline process so they can see how it works and like, kind of get that scary part of the way. Like something you wrote is now in production on Stack Overflow in front of hundreds of millions of people. Congratulations! But let’s just get that part out of the way. Um, but then how they can actually understand the code and keep building things, take on new tickets, work with product, size, refinement, all of that, we just ease them into that in their own pace, but keeping them exposed to that code through documentation and PRs really shortens the learning curve.
Kovid Batra: Cool. Makes sense. I think, uh, most of the things, uh, that I have seen, uh, working out for the developers, for, uh, the, the teams that are working well, the managers play a really, really good role there. Like the team managers who are leading them play a very good role there. So before we like end this discussion, I would love for you, uh, to give some parting advice to the engineering managers who are leading such teams, uh, who are looking forward to growing in their career also, uh, that would be helpful for them. Yeah.
Ben Matthews: Yeah. I, I, I, uh, I would say three big points that were big for me from that mentor. One, I’ve already spoke on of advocating for yourself. And, um, and for you, your team and your people, that’s a big part of getting visibility to, to try to grow, to show that you’re being successful. And, and, and honestly, just helping your other peers be successful. It’s a great way for people to see that you’re good at what you do. Another thing that, that I think people could focus on is building an organization that functions and not just executes. Those are kind of two different things, though they sound similar. For I can have a front end team that is great at pumping out front end code or building a new front end framework, and that’s valuable. They’re executing. But they have to work in concert with our back end team or DBA team, with product to align things, getting those things to work together, that’s an organization that functions. And though it may seem like you might be slowing down one to get them to work in tandem or in line with another one, um, that’s actually what’s really going to make your organization successful. If you can show that you have teams working together, reducing friction points and actually building things as one unit, that shows you’re being a good leader, you’re setting a clear vision and you’re, you’re creating the most value you can out of that organization. Um, and last I would say is, um, really identifying friction points or slowdowns in your organization, owning them and setting a plan on how to tackle them. There I had a natural inclination as I was moving up to hide my weaknesses, like to hide what was not going well in my organization. Um, and because of that, I wasn’t able to get feedback from my fellow leaders, from my manager or help. Um, but I would say if you have a problem that you’re tackling, own it and be like, “Hey, this is what’s going on. This is a problem I’m having here. So I’m going to address it.” And welcome any thoughts, but that’s another success story to share that you can tackle problems and things that are going wrong and also advocate for those. Uh, show that you can address problems and keep improving and making things better.
Uh, those three things I think have really helped me move forward in my career of kind of that mindset has made my organizations better, made my people better and let people know that, um, you know, I’m there to try to create the most value I can in the organization.
Kovid Batra: Makes sense. Thank you, Ben. Thank you so much for such a, such a great session, uh, and such great advice. Uh, for today, uh, in the interest of time, we’ll have to stop here, but we would love to know more of your, uh, stories and experiences, maybe on another episode. It was great to have you today here.
Ben Matthews: Thank you, Kovid. It was great to be here.
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