Unlocking Reddit's Secrets of Successful Hiring with Chris Slowe, CTO & Founding Engineer at Reddit.

(Joel Beasley at 00:00:00) Hello, my friends. I'm curious to know how many of you have a leadership pipeline. We know that great leaders grow companies because we talk to them here on the show every day. But what are you doing to create great leaders within yours? If you're a CTO, it is 100% your responsibility to grow and improve your people beyond just their coding abilities.

(Joel Beasley at 00:00:20) We've built a tool that improves your people in their craft and in leadership. Visit leaderbits.io to learn more. Today, we are talking to Chris Slowe, the CTO at Reddit, and we discuss ways to ensure you always hire the right person, empowering your brightest minds to make decisions, and important tips for getting the most out of your one-on-ones. All of this right here, right now on the Modern CTO podcast. Here we go.

(Joel Beasley at 00:00:48) This is the Modern CTO podcast. Alright, you feeling good today?

(Chris Slowe at 00:01:01) Yeah, yeah. No complaints. I just came from—this morning was my youngest, my youngest preschool graduation, which was a delightful experience. He was wearing a tiny little bow tie. It was very cute.

(Joel Beasley at 00:01:14) Oh, like a little gentleman.

(Chris Slowe at 00:01:16) Exactly. A gentleman, at least in appearance.

(Joel Beasley at 00:01:22) How old?

(Chris Slowe at 00:01:23) He's five, and he has an older sister who's eight.

(Joel Beasley at 00:01:26) Okay. I got one that's two and three, and then one that's three months.

(Chris Slowe at 00:01:30) Okay, you're just at the start of things. So, good luck, and there is a light at the end of the tunnel. There is a time after diapers, I promise.

(Joel Beasley at 00:01:43) I'm looking forward to that. We'll cherish that. So the oldest is a girl and then a boy? That's the same, that's what we got.

(Chris Slowe at 00:01:51) Does your oldest—is she in the obsessively mothering phase, or which way did she go?

(Joel Beasley at 00:01:58) She's dancing. She doesn't care. She doesn't even care. She's like—my wife texts me videos every day because all she does is run around the house and, like, hears her. Right?

(Chris Slowe at 00:02:11) Check with that.

(Joel Beasley at 00:02:12) So, alright, hold on. Come on. She grabs her foot and, like—

(Chris Slowe at 00:02:21) Yep. Oh, man. See, that's the difference. Well, mine are three years apart, and so I think that extra year, you know, she was actually aware that she had a brother, and so it's been like this, it's been a thing ever since then. That's adorable.

(Joel Beasley at 00:02:34) Then you can have one hold the bottle for the other, right?

(Chris Slowe at 00:02:36) That's the dream. It never worked out, but—

(Joel Beasley at 00:02:42) Oh, man. So are you out in San Francisco?

(Chris Slowe at 00:02:46) Yep. Guilty as well.

(Joel Beasley at 00:02:48) Nice. Where, like, what streets?

(Chris Slowe at 00:02:51) We are in the Tenderloin. So we're on Taylor and O'Farrell.

(Joel Beasley at 00:02:55) Okay. Cool. Yeah. For some reason, being in technology, I just happen to be in San Francisco a lot.

(Chris Slowe at 00:03:02) Where are you located normally? Or where are you now?

(Joel Beasley at 00:03:04) Florida.

(Chris Slowe at 00:03:05) Florida. Okay. Yeah.

(Joel Beasley at 00:03:06) Yeah. But so many things happen out there. And so I like it. The last time I was out there, I ran from, like, I can't remember the exact area, but I ran the bridge, like, all the way down and then to the bridge. I kept getting closer and closer and closer to the bridge, and my thirty-minute run turned into a three-hour thing.

(Chris Slowe at 00:03:25) It's deceptively far away. Like, it's actually, if you start off in the Marina and you're running along the coast, you're like, oh, I can totally run to the bridge. And it's about a three-mile stretch just to get there.

(Joel Beasley at 00:03:35) Yep. I was in a hotel, and then I was like, I think if I go down that street, you could actually see the water. And then I get to this observation area. I'm like, oh, that looks like a thirty-minute run over there, and it's an hour later. And then I'm like, alright, now I'm at the bridge. I gotta go over it. I get all the way over it, right?

(Chris Slowe at 00:03:49) Yeah. Me too.

(Joel Beasley at 00:03:50) And then there's this other area, vending area, sightseeing area.

(Chris Slowe at 00:03:54) Mm-hmm.

(Joel Beasley at 00:03:55) And so I was like, alright. My meeting—I was speaking at Williams Sonoma, which is down there. And so I was like, alright, I gotta give a talk in two hours. I gotta be back. I need to Uber back. So I flip open Uber, but where I am and the way the roads are, nobody—Uber forces them to loop around the bridge and pay a toll to come get me, so every ride just kept canceling on me.

(Chris Slowe at 00:04:16) Geez. Yeah, yeah.

(Joel Beasley at 00:04:17) I know. So then I'm like, alright, well, there's really no other place to go because most people have cars that get here. And so I was like, alright, maybe if I just run another mile that way down the road, it'll allow me to get an Uber. And it did. And I made it to the talk on time, but it was very scary, and my feet hurt a lot after that day.

(Chris Slowe at 00:04:40) Yeah. If you go down that—I know which path you went down, and there's actually a children's museum down there, going back to kids. So I actually live in Marin, on the north side. And so we spent a lot of time in that area, especially with two kids.

(Joel Beasley at 00:04:55) Yeah. Yeah. Because you can't be in the city city, right, with kids. You don't want to be in the city city with kids.

(Chris Slowe at 00:04:59) We lasted until we had the two kids in a two-bedroom apartment situation, at which point things just fell apart rapidly.

(Joel Beasley at 00:05:07) Yeah. You gotta let them run outside too, right? And you can't do that when there's people on the sidewalk.

(Chris Slowe at 00:05:14) I know. I know.

(Joel Beasley at 00:05:19) So, CTO Reddit, very cool, right? But you didn't start there. You didn't just wake up one day and you're CTO Reddit. Where did you start? Where did you—speaking of kids, right—when did you first fall in love with technology? Was it video games, computers?

(Chris Slowe at 00:05:33) Oh, boy. So if you want to go way back. Yeah. So I think, so I am of a slightly older vintage. I'm 40, which means, actually, that makes me, wait, Gen X, I think, technically speaking. I had my first video game system was an Atari 5200, which I got when I was about maybe six or seven, which was a heck of a lot of fun. And my first exposure to computer wasn't until I was in high school. So we had a 486 when I was 14 that I really just kind of fell in love with and started immediately trying to figure out how to program against it. I think at the time it was I was writing in QBasic and trying to write very simple video games. The whole time, though, I was actually much more of a science nerd than a tech nerd. I mean, this is the early nineties. And so I originally went to—I went to school actually not for computer science, but for physics. Did physics and math for a while and actually got involved in the tech scene when I was in my fourth year in grad school, and went through a pretty standard experimental degree burnout that happens right around that time. Grad school and experimental science is this discovery that you spend maybe, if you're lucky, three to 4% of your time doing actual science and then the rest of your time doing everything else. So I spent a third of my time in a machine shop building stuff. I spent a third of my time on a computer analyzing some results that I had or building models. And I spent a third of my time doing all the other miscellaneous stuff involved in the experiment. The nice thing is it was actually like nerd finishing school. So I can weld. I know how to do plumbing. I used to legitimately walk around, non-ironically, with pliers on my belt for most of my time in grad school for the full seven years. Because at any given time, there was a potential of me having to hold something together while it was falling apart, and having a pair of pliers available at all times really helpful. So, to make a long story short, what ended up happening was around that time is 2004, 2005. I had a friend of mine who was also a scientist pitch me on this idea. I will use modern words. He pitched me on what turned out to be a startup, but at the time, it just seemed like, hey, you know what's really annoying? It's really hard to find stuff on my hard drive. And this is at a time when the state of the art desktop search was like that dog that would come up on Windows XP and ask you what you were looking for.

(Joel Beasley at 00:08:03) Not the paper clip? Dude, you switched from Clippy to the dog?

(Chris Slowe at 00:08:06) Well, I just remember that being one of the stock ones that came up. Originally, I think, Microsoft Bob was the origin of it that they kind of ported into being the help system. And I just remember thinking, yeah, this is going to be a simple solution for this. And like most things, the first mistake is always that initial ignorance of not knowing how hard the problem really is. It's like, oh, this is like, I'm just going to write a thing that searches for files on my computer. That turned into a startup and then actually turned out into me getting into the first Y Combinator batch in summer of '05. So we ended up pitching this—me and my cofounder pitched this idea of solving desktop search. And this is pre-Spotlight. This is pre-Google Desktop, and pre everything being on the cloud on the web anyway. And so that was kind of my origin story on getting into tech. It was totally circuitous. So, I mean, I ended up actually finishing my degree and continuing down some of the science path. But I think part of the discovery of doing a startup at that point was that I was able to find that the outlet that I liked in academia was this kind of, there's a problem that's hard. And if I break it down into pieces, I can solve it and then have something to show at the end and achieve something and further humanity, right? And I think that tech, the roots of tech, are very much in the same thing, which is that there's a set of fundamental problems. There are things that we're good at, and there are things that computers are good at. And if we can make the computers do our work for us, our lives can get better. And that was really, I think, the root of the journey.

(Joel Beasley at 00:09:34) Now I'm one of those people that whenever I hear something I don't understand, I have to ask about it.

(Chris Slowe at 00:09:38) Yeah.

(Joel Beasley at 00:09:38) Sure. Tell me about that word you use, circuitous.

(Chris Slowe at 00:09:42) Oh, circuitous. Just like, circuitous is, like, not taking the direct path, but taking the long meandering path and ending at the same place.

(Joel Beasley at 00:09:53) Oh, man. Yeah. That sounds like a lot of decisions in my life.

(Chris Slowe at 00:09:56) I know. The nice thing about getting older is you get a chance to have some hindsight and discover how many things in your life are just the side effect of some random event that happens, right? It's the John Lennon quote, I think, the Beatle, not the communist, who I think said that life is what happens when you're making plans. And I think that's sort of true here. It's like, you know, I ended up getting involved in the—the roots of me getting involved in startups was, legitimately, you know, the way that my original startup kicks off was I happened to randomly go to a talk while at grad school. And I happened to run into this person, Zack, Zack Stone, who ended up being my cofounder. We knew each other. We weren't friends at that point. And we ended up striking up a conversation. And it was one of those—that random conversation turned into effectively the catalyst for my entire career. Because otherwise, I was kind of not necessarily dead set on being an academic for my whole life, but at least was on that trajectory.

(Joel Beasley at 00:11:02) And so today, Reddit is essentially a household name, right? But it's not just a clear, perfect, beautiful path from let's cofound Reddit to it being the behemoth it is today. Tell me a little bit about how your role evolved, what you learned. You were—I guess, were you ever a team lead or anything like that prior to being the CTO of Reddit? Tell me about that.

(Chris Slowe at 00:11:27) Oh, yeah. No. It's been a long journey. So the other rest of the story is, my start at Reddit was I was Reddit's first employee. And so I got involved with—so, you know, Reddit was founded by Steve Huffman and Alexis Ohanian in summer of '05. And they were also in the first Y Combinator batch, which is how I met them in the first place. And so another one of those kind of totally random events that changed my life was, yeah, at the end of the summer, my startup failed. And I had an apartment with two free bedrooms, and I was friends with Steve and Alexis. And so they moved in. And then two months later, I was working on Reddit. And, you know, at that point, that was very much the—I mean, it was the in a crappy Somerville apartment version of the bunch of nerds in a garage or in a basement just kind of working on something. Like, we had this office that—our office. Our office was our living room, and we're in this third-story walk-up in Somerville, Mass. And the floor in the office was nothing even close to level. Like, if anything, it was actually kind of V-shaped. So if you're sitting in a chair with wheels and you let go of one of the desks, you would just fall towards the middle of the room. Like, it was really, really janky. And so it was—the startup was very scrappy. The whole experience was, you know, learning how to develop a functioning web app live while you're doing it. And so that was much of the experience for the first, you know, five years. It was a very, very small team. We got acquired originally by Condé Nast in '06 and kind of got pulled in to that company and just kind of were mostly left to our own devices to kind of continue to iterate the product. And it was really just, we were doing what we thought was best, not really knowing what was right or what was wrong or how to actually do it. So, for me, the path to CTO was actually much later. So, you know, after four years working at Reddit, post-acquired, so Steve and Alexis left in '09 to do other things. I left in '10 and ended up joining back up with Steve to work another startup. And that was where we did a startup called Hipmunk, which is a travel startup.

(Joel Beasley at 00:13:38) What? The hip chipmunk? Yeah. Yeah. I know the Hipmunk.

(Chris Slowe at 00:13:44) Okay. Well, that was Steve—Steve was CTO at that company. And so I kind of jumped back over to work with him, and that was where we actually got a chance to do all the other things that a company needs to do to become a successful company. Like, so Reddit was always kind of in a state where it was very small staff. We never really had to do things like grow it. The traffic was totally organic and it always grew. And in fact, one of those pitfalls we had with starting Hipmunk was we just had this preconceived notion that, you know, the way that you launch a product is you just kind of put it on the web and these people just come. Because, like, that's—I don't know what you're talking about. There's a lot marketing and launching. Like, what? You just put it up.

(Chris Slowe at 00:14:29) And then we discovered really quickly that, oh, no, that's not a normal behavior. And so then you gotta learn really quickly how magical Reddit is as an experience. But what Reddit was lacking was we never built the actual company around Reddit. We got acquired as a very late startup and we were always small.

(Chris Slowe at 00:14:46) And so Hipmunk was great because it gave us an opportunity to learn all the rest of it, right? Like, how to grow and scale a team, how to actually hire good managers, how to be a good manager, the importance of getting good talent. When is it important to have an HR person? You know, what exactly do these PMs actually do? Why do I care? Oh, and designers. You mean somebody makes things look good for you without you having to figure it out? That's just wonderful.

(Joel Beasley at 00:15:12) I know.

(Chris Slowe at 00:15:14) And so it was really enjoyable and enlightening. And, you know, we grew that company up to about a hundred employees. And so at that point, I was doing engineering management and had gotten the—I was running the back end team there. And then switched over to—decided that, you know, Reddit was going through some tough times in mid-2015 and came back in early 2016 to—I'll say I thought I had mentally divorced myself from the company in a lot of ways, from the product, but then I discovered that actually, no, I felt like a parent still. Like, I wanna make sure things are okay.

(Chris Slowe at 00:15:52) So came back originally. I was doing IC work and then just started building teams. What ended up happening at that point?

(Joel Beasley at 00:16:00) I'm curious about the building teams part, right?

(Chris Slowe at 00:16:02) Yeah. So one of—

(Joel Beasley at 00:16:03) One of the things that I've found to be true is that your vibe attracts your tribe, right? Like, the people who you are, you'll attract as you get this mass. You'll start attracting other people that are similar to that. Was that true for you as you started growing your teams?

(Chris Slowe at 00:16:21) A little bit. So I think what happened initially was the state of Reddit in 2015, 2016 was still very small given its reach, right? So, you know, the company at that point had 215 million monthly active users and the total size was around, I wanna say, 60 or 70 employees, which means engineering was only about 30, right? So very, very small team. And that was basically split down the middle of, like, half back end, half front end, a little bit of mobile in there mixed in. So just enough of a team to be able to keep the ship running, but not really to evolve the product. And so, you know, the original mission and the job upfront was actually turn the company into a functioning business and turn it into an actual working company. And the first thing to do there is hiring.

(Chris Slowe at 00:17:11) Like, actually getting people in, working through the fact that, you know, there was a lot of stagnation in the meantime. There's a lot of things that hadn't really been developed. It was actually gonna—it was a little funny coming back for me, especially because, and I think for Steve as well, because, you know, we had spent five years building another company and learning a bunch of things. And then coming back to Reddit, it was a little bit like coming back to this parallel universe where they chose a different path. Like, we're like, oh, oh my goodness, they never invented that here. You have to, you know, figure out how to apply these things we learned. I can't bring you fire. And so the initial version of that was starting to structure into engineering teams as opposed to being ad hoc groups. We had a lot of tech leads and not a lot of actual managers.

(Chris Slowe at 00:17:56) And we had a whole bunch of very clearly identifiable gaps. And so my original role was, like I said, I was doing IC work, and then I started to basically—I was talking to our CTO at the time, Marty Weiner, and I kind of gave him my list of things we need to get built. And he's like, great. Why don't you go start one of those teams? And so the first team I started when I went back was this team that does all of our site integrity work called—that has a great name—Anti-Evil.

(Chris Slowe at 00:18:25) It is their job to build tools to make sure that users remain safe and that the site has a certain amount of integrity to it. Very, very important job on a social platform like Reddit. And so really just carved out a couple engineers and started building that team. And then it quickly turned into—through no fault of my own—accumulating teams. So I think my, you know, whatever the opposite of a land grab is, it was just like that. It was like, okay, it's going right over there. So here, Chris, have another team. So I quickly assumed the role of director of most of our back end teams, platform.

(Chris Slowe at 00:19:01) In the meantime, we also hired a VPE, great guy by the name of Nick Caldwell, former Microsoft. And he came in and also helped us level up in terms of figuring out what engineering org structure should look like when you have, you know, eventually a hundred-plus engineers, to start to get some structure in place. And so I started as CTO two years ago now. So it was a very rapid ramp up over the course of a year. And then all of a sudden discovering that I'm now in charge of the ship, which is, you know, existentially terrifying, but also very gratifying.

(Joel Beasley at 00:19:43) On that climb, what are some of the biggest takeaways, the biggest—or just we could just pick one. Like, what's one huge lesson that you've learned over and over again?

(Chris Slowe at 00:19:53) Oh, I mean, I think that the real importance of hiring and finding the right people. You know, I think that there's a couple big lessons there. One is we've always driven to make sure that we hire people who are passionate and who also have a certain amount of humility with the work. And I find that just from personal experience that, you know, there's this thing called the—actually, there's a well-known effect called the Dunning-Kruger effect that I didn't mention before, but I will bring up now. The Dunning-Kruger effect is that when you're confronted with a new problem, your first response is usually to say, oh, this is totally easy. I know exactly how to solve this, right? And you are invariably 100% wrong. Like, you invariably—so if you look at your level of confidence as a function of time, you're immediately very confident. And then you discover how quickly that you're incorrect, and you end up plummeting into this chasm of despair, is usually what it's called in the graph. So the peak is called Mount Stupid, and then you have the chasm of despair. And then you spend the rest of your career climbing back up, and you never achieve the level of confidence you had in that first few minutes of, like, oh, this is totally easy. Because the more you know, the more you know, and the more you know your own gaps. And so I find that one way to short circuit that is if you've been through that experience enough, you realize that most things are not actually easy. And that incurs a certain amount of global humility in your approach of, like, this will be hard, but I will deal with it, you know, as the upfront thing.

(Chris Slowe at 00:21:24) And so I find that that is definitely an important characteristic to be able to suss out early on. I also think the function—a little bit of stage of the company—is important, right? Like, having a bunch of very determined hotshot people is extremely valuable at the startup stage of the company, and it can be very, very difficult at a larger stage company where everyone has much more specific roles, right? You know, if I've got a 10-person engineering team, everyone has to know what they're doing and has to be self-driven, and there's no way possible for me to—they will work it out. When you get up to a hundred people, you have to have a lot more structure in place just because you don't want people stepping on each other's toes, and you need to make sure that there is clear coordination and clear communication as opposed to, oh, I don't have to worry about it because I know, you know, she's working on it over there. I might not even know who she is. Like, there's an entire team that's in charge of something that might be out of my control. So that's been a big one.

(Chris Slowe at 00:22:21) And I think that the other part of that is really when it comes to mentoring and making sure that people are able to progress in their careers, you know, it's much more worth everyone's time if you're working to improve the people who you have that are already good as opposed to trying to salvage a situation that went wrong because you hired incorrectly or because there wasn't a fit upfront.

(Joel Beasley at 00:22:47) Yeah. That's investing in your people and turbocharging the existing people who are already running is a super, super valuable use of time. So as a CTO currently, where—if you were to make a pie chart of the top three ways that you spend your time, what would that look like?

(Chris Slowe at 00:23:06) Well, I should mention right now that I'm currently dual-wielding as CTO and VP Eng. So I probably have two distinct pie charts.

(Joel Beasley at 00:23:15) Okay. Let's start with the CTO pie chart.

(Chris Slowe at 00:23:18) The CTO pie chart—I think that most of the—so the CTO role at Reddit is primarily one of being a chief architect. And so I have a small office of CTO group of four engineers who are company-level architects, very senior folks. And their job is usually described—I describe it usually as extreme tactics and extreme strategy. So either their job is to drop in and add a whole bunch of help and firepower to something that is falling apart or it's on fire, or start to make sure that we have a plan for making sure that we don't have a fire six months from now. I'd say the current intermix that I have for that work is probably still about 80% firefighting and, you know, 20% making sure we don't have fires in the first place.

(Chris Slowe at 00:24:07) And, you know, my job is to start to shift that function up towards strategy to make sure that we really do have a long-term plan, strategy. Another important bit there is that, you know, as the company gets bigger, one of the natural states of affairs is that it gets a little bit more siloed. Everyone has their role. But we're a single company, and there has to be some way to connect together all the initiatives into an overall goal and to make sure there's a place to land work that is pan-engineering. And so that work ends up landing either up on my plate or at least up on OCTO's plate to figure out. So that would be probably the biggest part of the CTO role. For the VP Eng role, I mean, the clear part is execution, figuring out how to take the product plan and the engineering plan and turn them into the plan and make them into something that is actually executed and trackable. Wrangling OKRs, making sure that people have clear goals, expectation setting, management, of course. You know, I have a team of eight directors who are keeping the ship afloat.

(Chris Slowe at 00:25:16) I think the fun and terrifying part about being both VP Eng and CTO is that, you know, the natural state of affairs—I think it's not as extreme as for being CEO—but the natural state of affairs is that I wanna make sure that everyone who reports into me is far better at their job than I would ever be, right? Like, they need to be just great at their thing. And so my job is to facilitate them being as productive and as enabled as possible and to get out of their way or provide air cover. I think the joke I usually bring up is that, you know, all orgs end up naturally being shaped like a pyramid in a hierarchy. I think the right way to set that up is to actually have the point on the bottom. So you wanna be there to support everyone who's above you and make sure they can be their best.

(Joel Beasley at 00:26:07) I like that. We'll have you teach a class called, like, the upside-down pyramid.

(Chris Slowe at 00:26:15) It's reading for a book or potentially a band. I'm not really sure which one I wanna go with.

(Joel Beasley at 00:26:19) The upside-down pyramid? Yeah. I like that. Well, talking about management and engineering, I was talking with the CIO of Atlassian. You're familiar with them, right?

(Chris Slowe at 00:26:31) Yep.

(Joel Beasley at 00:26:31) And we were talking about engineering performance management and this concept, like, sales has metrics and they look at—they're very metric-driven now, right, with the software. Marketing is very metric-driven with cost to acquire things. And then they were looking for, like, where are the metrics in engineering? And I came across this company, this whole—this new category, sort of an emerging category called engineering performance management. Have you heard about this yet?

(Chris Slowe at 00:26:56) I've seen some companies that are getting into this. Like, I think the ones that come to mind are usually tools that write on top of GitHub or tools that write on top of Slack and try to do a little bit of, like, um—I can't not say the word creepily—you know, kind of keep track of everything that's going on and figure out where there's inefficiencies in the process. But I'm curious to hear some of the ones you've seen.

(Joel Beasley at 00:27:21) Yeah. So I had this guy on my show from—he did Appcelerator previously. Remember that company? And now he's doing this thing called Pinpoint. And very, very cool. Him and his cofounder have had this amazing relationship for the past 19 years, which is really cool. Like, to do multiple companies with the same person over 19 years is really interesting because, you know, we're always talking about trust and cofounders. And so I was like, this is a picture-perfect relationship. So I was actually interested after we spoke. And so I was like, hey, like, let's see what it actually does after the interview. He gave me one of his—his cofounder and then he did a product demo with me so I could see it. Dude, it is so—like, this stuff is really cool. I can't even describe all of it. I'm not even gonna try. But all I'm saying is that that category of software is definitely something that I believe is going to—there's gonna be a hundred of those companies right now. I think there's only a handful, but I believe in the next three or four years, there's gonna be a hundred of them.

(Chris Slowe at 00:28:21) Yeah. I mean, you know, it's something that I definitely struggle with or at least as an org, we struggle with a little bit because, you know, it is a little bit harder to define engineering productivity if only from the standpoint of—I think what's underestimated for engineering work is that it is ultimately a creative endeavor, right? Like, you can't just say, like, work harder or ship more lines of code or have a straightforward, you know. There's an old—I mean, there's an old story about—I always forget, I'm terrible with names in general, and I'm gonna butcher this story, but I'll give it anyway.

(Chris Slowe at 00:28:52) The story about how early on, I believe it was Apple, used to measure productivity just by straight up lines shipped. Right? It was very early in their career as a company, and they hired this guy who knew—let's just say he knew what he was doing. He's very good at his job.

(Chris Slowe at 00:29:12) And his first commit was a negative 10,000 line plus 200 line commit. And it was just this demonstration of, like, oh, actually, okay, so this guy just has, therefore, negative productivity by our measurement, even though he effectively made this thing faster and more efficient. And so I think that the one way we're trying to actually solve some of this is we're just looking at things like, almost developer happiness is the first thing to touch. Right? Like, do developers themselves feel that they're being productive, or are they being bottlenecked on things? So, you know, good old-fashioned survey of like, did you think that you were stuck on, or what do you think we could have improvements? And that at least has helped with facilitating starting to find, like, yeah, we know that our developer setup is not optimal right now. Right?

(Chris Slowe at 00:30:10) But also identifying that, oh yeah, it's actually really easy for a developer to break the build on our developer version machine. And then find out, like, okay, so if they break the build, that means every engineer in the company has to spend an hour fixing their broken build. Well, that's a lot of time wasted when you add up—you know, that's an entire engineer month at our scale.

(Joel Beasley at 00:30:30) Yeah.

(Chris Slowe at 00:30:30) And that only gets worse. And so, being cognizant of that kind of level for us, I think, is the starting point.

(Joel Beasley at 00:30:38) Sounds like a project for your super team.

(Chris Slowe at 00:30:40) Yeah. That'd be like, oh man, if I had more capacity for my super team—I should rebrand them as super team. That would be a good idea. Do they get capes for that? I think they probably get capes.

(Joel Beasley at 00:30:52) Either capes or snuggies.

(Chris Slowe at 00:30:55) Capes and snuggies.

(Joel Beasley at 00:30:56) Capes and snuggies? Just let them pick. Every battle they win, they get a new accessory.

(Chris Slowe at 00:31:03) What about, I mean, maybe like a sash?

(Joel Beasley at 00:31:06) A sash.

(Chris Slowe at 00:31:07) Badges that they can accumulate. I think that would be a good way to go. Like, almost like, you know, military regalia to make it feel very—well, military might be too extreme, but we'll figure something out.

(Joel Beasley at 00:31:15) It also gives more flexibility when like, a snuggie would confine you a little bit. You know? So you want the ability to move because you have to run to the emergency. I assume that that's what they do. They run with their laptops to the location.

(Chris Slowe at 00:31:28) Yeah.

(Joel Beasley at 00:31:28) Yeah.

(Chris Slowe at 00:31:29) Actually, we have fireman's poles and parachutes. It's very dramatic. We had flash powder for a while, but it was a bit of a fire hazard.

(Joel Beasley at 00:31:38) Yeah. And somebody—Bob had allergies. So—

(Chris Slowe at 00:31:42) Don't get me started on Bob.

(Joel Beasley at 00:31:47) Oh, man. This is good. No, I really like you. You're a pretty great person, man.

(Chris Slowe at 00:31:52) Thank you very much.

(Joel Beasley at 00:31:54) But you never know when you're going to these interviews, right?

(Chris Slowe at 00:31:58) I think, you know, don't forget one of the features of the job is having to spend a lot of time on Reddit. And I would like to say that I'm actually—one of the side effects of being on Reddit for so long is I'm actually much funnier in text form. So I apologize if this is the version you get.

(Joel Beasley at 00:32:16) It's adequate. Okay. Let's go back. Let's get the audience some love. So we get people to write us, like, write and ask us questions, and then I ask them to the guest. First question: How do you do one-on-ones? What's, like, the cadence? Like, how do you approach that?

(Chris Slowe at 00:32:36) Okay. So I think, having had a lot of different hats over the last five years, I've varied a little bit by level. But I'd say that one-on-ones, it depends on the level of person you're kind of doing one-on-one with. I think when back when I was an engineering manager, my general rule of thumb was I would do biweeklies with all of my kind of established people and then weeklies with anyone who was very junior or new to the team until there was a good notion of a cadence. Generally, one change I've made over the years has been I've gotten much more into being a little bit of an agenda, like, you know, required doc. I like having a place to refer to for what we're going to talk about. And if only because it enforces a certain amount of structure on the discussion, you know, it means you can do things like say, like, every four weeks, we're going to talk about your professional development, which is something that I think is easy to fall by the wayside otherwise. It also gives you a chance to take what can be a very unstructured discussion and turn it into actionable things that you can do before the next meeting or as, like, ways to make progress. And so I've gotten very much into that approach of, like, let's have a doc, the good, the bad, and just miscellaneous topics. And I think, you know, with more senior talent and with directors, there's also sections that involve OKRs specifically in the one-on-one doc.

(Chris Slowe at 00:33:57) Not OKRs necessarily for their org, but for them and their org kind of combined. Like, what do they want to achieve? And then it provides an outlet for checking in. And so I think that—and the last bit is actually, over the last few years, I've definitely gotten very much into making sure there's an outlet for feedback and for candid feedback as part of a one-on-one. And making sure that it's as bidirectional as possible is important.

(Chris Slowe at 00:34:22) I would say that I've definitely learned that written feedback, though harder, is also generally more effective. And the structure that seems to work for me is, when it's come up, if you have it as part of the one-on-one, then there's always an outlet for it in the doc. And it means you have to kind of collect your thoughts and get it down first. It also means there's less room for ambiguity as long as the purpose is to inform the other person and to have the chance to talk about it live. Right? So it's not like I'm going to send you an email with a bunch of feedback, and then I hope you do the best with it. It's like, no, we're going to sit in this meeting, and we're going to read the feedback, and we'll talk about it and try to figure out a solution to it. I think that's had a very—you know, it's had a little bit of structure to meetings, but at the same time, the structure is generally good because it means that there's an outlet for that kind of information. But I think, you know, I'm sure that one of the things you hear the most is, like, just getting candid feedback is just the hardest, most valuable thing you can get.

(Chris Slowe at 00:35:21) And it kind of comes back to the humility parts. Like, if you're not a little humble, you're not willing to accept feedback, then you're not going to really internalize it or progress from it. Like, the person is giving you a gift by giving you feedback. And maybe the gift is we have poor communication and we have things to talk about. Or maybe the gift is like, hey, you're actually doing a great job. Thank you for being so good at your job. Like, it doesn't have to be always constructive feedback. I mean, it is actually good to hear stuff that's going right.

(Joel Beasley at 00:35:56) Yeah. That's—I actually have one of those today. Yeah, I was giving feedback to—you know how you told me about designers, right?

(Chris Slowe at 00:36:01) Yeah.

(Joel Beasley at 00:36:02) Well, we had a designer start about three weeks ago, Pam, and she's, like, straight killing it. Like, she's doing so good. And I did that thing where, like, I had an idea, and then I had another idea, and she didn't jump and adjust and do the thing that I was most excited about. She finished her work and prioritized it herself. And I was like, just thank you. Like, thank you so much because that means you can self-organize and I can just keep feeding you stuff and you can organize it and I don't have to worry about, like, having a special Pam, don't tell her this now list and all this stuff. And, yeah, so I was like, that's amazing. I'm super glad that you have that skill, and so that was my feedback with her today.

(Chris Slowe at 00:36:40) Yeah. And, you know, it is really easy to just kind of dwell on the problems and not really take the wins. Like, you do have to actually recognize people for the good stuff they do, and it's kind of an important part.

(Joel Beasley at 00:36:50) Right. Recognition makes people feel good. And it's true. And when it's true, when you have an opportunity to allow someone to feel good, like, do it. Let it happen.

(Chris Slowe at 00:37:02) Look, it also goes back for me to the creative element question and the stuff around making sure that you're actually fostering people who are good at their job. Right? You know, somebody actually is legitimately killing it and you can help them to kill even more, then that's a way to do it is to say, like, yes, you are doing the right thing. Continue doing the right thing. And that's speaking as somebody with a huge amount of imposter syndrome.

(Joel Beasley at 00:37:30) Oh my god. I don't even know what to say right now.

(Chris Slowe at 00:37:32) Yeah. It's the end of the day.

(Joel Beasley at 00:37:33) I'm like, I'm all excited. I don't know. I've got a—

(Chris Slowe at 00:37:35) I've got a couple extra hours on you. It's only 2:00 here. So—

(Joel Beasley at 00:37:37) It's only 2:00?

(Chris Slowe at 00:37:38) Yeah. Okay.

(Joel Beasley at 00:37:42) Next question. I don't even know how to do it. I'll just text it to you. No. You make a lot of big decisions, right? Or we'll just say that you do. And yeah, you're a senior leader at an enterprise, you said. And so decisions, things that come up, what advice do you have in the decision-making space? Like, what's some of your good nuggets of knowledge there?

(Chris Slowe at 00:38:09) Well, I'd like to go back to my statement before about that, you know, one of the things about being a senior leader is that, ideally, the people who work for you are even better at their job than you would be. Right? And I think that in that case, part of the role of being a leader is actually to get out of the way of people and let them do their job. I think it kind of comes back to—you're talking about your designer and her ability to prioritize, right? Like, if I am doing too much micromanagement of anyone on my team, something is pathologically wrong. Right? I mean, the whole purpose of having a team to start with and the fact that we're not a 10-person startup is because we want to have a whole bunch of people with different perspectives and with different ideas be able to organize and solve problems. And so, if anything, I find that one of the roles of being the kind of leader in a room when there's a discussion or meeting or debate is that oftentimes, your people know what the answer is. They just need somebody to tell them that, like, it's okay for them to do that.

(Chris Slowe at 00:39:06) Or at least, they just need to talk it out and convince themselves they're right and convince somebody else in the process. And so just kind of being there to—I usually joke it's like a rubber stamp for me. It's like, just go do it. It's not because I'm just saying that I don't have an opinion in the matter. It's them saying that your opinion is probably more important than mine. And like, why are we even talking? Like, let's go do it. And then, of course, it varies a lot by—it varies by experience. It varies by level. I mean, like, you know, I have the luxury of having a bunch of very senior leadership also reporting to me. I think when it comes down to, you know, rank and file, when you're talking about ICs and EMs, it's the same kind of direction that happens. People become experts at their job, or they should be allowed to be experts at their job and therefore be allowed to make decisions and not feel like they're going to be countermanded. And that's not to say that we're always going to say yes to everything or that I always say yes to things that are presented to me. Sometimes things are timed wrong or have to be delayed or it comes back to prioritization.

(Chris Slowe at 00:40:04) Like, yeah, this sounds like a really good idea. Is it a now kind of idea or, like, you know, how does it compare to these other 30 things that we need to do? And if you tell me it's number one, then we can have that debate. Then, yeah, let's go do it. If it ends up being number 29, which is usually the case, then usually that discussion helps to foster the reasoning behind why we're not doing it now or why we're not doing it at all in some cases.

(Joel Beasley at 00:40:26) What's, like, the biggest priorities on your mind right now?

(Chris Slowe at 00:40:30) Oh, man. So I think the big one for me right now is—so last year, we did a major desktop overhaul for the website. You know, it was a very quiet thing. Nothing really happened from it. It's Reddit. Nothing ever happens on Reddit. And that went really well overall. It took a good year in the making, and it took a good year and change to kind of roll it out gradually to make sure that we listened and provided outlets for feedback and encouraged—speaking of feedback—we're doing the same right now in our back end. Our back end is mostly a 10-year-old now monolith. It has a lot of my fingerprints all over it. And so I am actively working to get all of my blame off of the code base. I mean, by the thing, I'd say, you know, we're doing the kind of standard things. We're moving to services. We're starting to build out a more modern stack while the whole thing is flying and making sure we don't break anything in the process. So it's a very exciting and delightful and terrifying experience.

(Chris Slowe at 00:41:29) And I actually—it goes back a little bit to productivity on our side. You know, a monolith is a great thing and it's a stable thing. It's not a great thing when you have 160 engineers who need to work on things on it.

(Joel Beasley at 00:41:40) When you said you're going to bring it back, I thought you're going to bring it back to kids because you said terrifying. I was like, so you're going to bring it all the way back to the beginning? I was like, this is great. I was like, you're wrapping up the show for me, man. This is awesome. Okay. I got to run a hypothetical past you.

(Chris Slowe at 00:41:55) Yeah. Go for it.

(Joel Beasley at 00:41:56) Alright. You're in San Francisco. Alright? You're driving down the street. Alright? Not in an interview. Not in a podcast. You're driving down the street. And at the red light next to you, guess who pulls up next to you?

(Chris Slowe at 00:42:08) Who?

(Joel Beasley at 00:42:09) Elon Musk.

(Chris Slowe at 00:42:12) Oh, yeah. Okay.

(Joel Beasley at 00:42:14) You like this? Okay. He's like, rolls down the window. It's like, "What up?" And he's like, "I just built this new invention. You want to come check it out? Follow me to my house." So you're like, "What the heck? Let's follow Elon Musk."

(Chris Slowe at 00:42:27) As anyone does. Yeah, yeah, yeah.

(Joel Beasley at 00:42:30) He regularly does this, by the way.

(Chris Slowe at 00:42:32) He does that. I do that. Yeah. Yeah.

(Joel Beasley at 00:42:33) He's known for this. Yeah. Yeah. And so you follow him. You're at his house, and he shows you this, and he takes you in his room.

(Joel Beasley at 00:42:40) He's got a time machine. But here's the deal. You go into the time machine, and you can only go back to Harvard, right, where you were studying. You're welding, right?

(Joel Beasley at 00:42:51) You're welding. You're studying. You've got the belt on, the pliers. You're welding at Harvard. You can go back to this exact moment, and you can gently whisper some advice into your ear. Some, and that's it. That's it. Just this little whisper of advice. What would it be?

(Chris Slowe at 00:43:07) Oh, that's a tough one. So this is going to totally wreck my, well, so going back to my career feels like it was a series of fortuitous events that kind of accumulated into the result. How much of the card castle am I destroying by misadvising myself? I don't know.

(Chris Slowe at 00:43:26) I mean, my joke answer would be probably buy Bitcoin in 2009, right? I mean, yeah. I'm definitely straight up, this will fix everything. I think, oh god, that's a tough one. So I think a lot of the stuff that's been most valuable has been by experience. And the actual, maybe that's the basic advice, is that the journey is kind of the point, right? The destination is less important than the journey.

(Chris Slowe at 00:43:56) Because I think that, especially getting to my own head in grad school, I was all about, yeah, if I get my degree, then I get my degree and I can start working on my post doc, and then I'll work on getting a professorship and these big milestones that kind of lay out for yourself. When in actuality, life's a heck of a lot more complicated than a bunch of milestones that you kind of accumulate for yourself. So I'll stick with that one. I'll say it's about the journey, not the destination.

(Joel Beasley at 00:44:19) I love it. And it's good. And it's true, right? It's a great piece of advice. But you did bring up, you did bring up something in my mind. Is the, here's the question. I'm going to try to form it right now. Is the journey more special having a milestone, having a destination?

(Chris Slowe at 00:44:40) I mean, I think, you know, it's funny because actually, this is something that we do think a lot about as a company right now, which is, you know, we talk a lot about North Stars in the company and goals. And to answer your question directly, yes. I think that the having a destination in mind is always important. Because otherwise, you know, what is the point? And it kind of comes back to one thing we bring up a lot here, which has been this potentially totally false anecdote about NASA in the sixties where, you know, all of NASA was set up in the sixties to be about putting a man on the moon.

(Chris Slowe at 00:45:17) And they'd set up their culture in such a way where if you asked literally anybody at NASA, down to the janitors who are mopping the floor, what is your, what are you doing here? They would respond, I am working to put a man on the moon. And they were able to connect their story up to that goal. I think that that part is important. I think that the learning for me is that the result might not be to achieve that goal, but that doesn't mean that the original goal was false.

(Chris Slowe at 00:45:49) Right? Sometimes a goal is a means to a better goal, and you just don't have the insight to figure out that you're going the wrong direction.

(Joel Beasley at 00:45:57) I like it. What's the big mission do you have for Reddit? And we don't have to, we could edit this part out because we already have the answer. We already had the great answer at the end about the advice you give your past self. The interview is over, but I just want to know, what's the big thing at Reddit?

(Chris Slowe at 00:46:12) I mean, you know, I think we're always just trying to make, honestly, just continue to grow the platform and make it better. It's a really, I mean, it's a mundane response. But honestly, I think for, one of our biggest learnings over the time here, you know, Reddit is this wonderful beast now that's almost 14 years old. It'll be 14 years old this month. It's gone from being a small hosting board effectively into a giant collection of network communities.

(Chris Slowe at 00:46:42) Right? And one of the lessons we've learned over the years is that, fundamentally, our users are always more creative than we are. And so our job is to build things and build tools that allow our users to express creativity in ways that surprise and delight us and helps kind of foster the platform. So, you know, for me, I just want to continue to see that happen. And I think that, you know, being a technologist, I have at my disposal the tools needed to build those tools and build that technology that makes it work.

(Joel Beasley at 00:47:12) Yeah. So build communities or serve the community. I mean, that's essentially what you guys do. You serve the Internet. You're a portal. You're a filter for the Internet.

(Chris Slowe at 00:47:23) Yeah. I mean, I think we've tried to figure out exactly the best way to describe what Reddit is. And I think the one that we've been settling on recently has been, Reddit's a city. It's a giant city that has neighborhoods, and the neighborhoods all have their own flavor. And as a city, it's going to have every aspect of humanity present. And so you're going to see the good and bad. And the point of a city is that you do get a chance to see the good and bad, right? Everything's out in the open. Nothing's hidden.

(Joel Beasley at 00:47:50) There's your North Star. What are you doing? You go up to the janitor. What are you doing? They say, we're building the city.

(Chris Slowe at 00:47:56) I like that a lot, actually. That's a good one.

(Joel Beasley at 00:47:58) Build the city.

(Chris Slowe at 00:47:59) The city. That's good, actually.

(Joel Beasley at 00:47:59) That's it. That's what you guys are doing.

(Chris Slowe at 00:48:01) Yeah, right? Yeah. Actually good, actually.

(Joel Beasley at 00:48:05) I'll send you a bill. Marketing and advertising branding. Sorry. Oh, man. Dude, we did it, Chris. We made a podcast.

(Chris Slowe at 00:48:18) That was fun.

(Joel Beasley at 00:48:19) Awesome. Dude, this was fantastic. Thank you so much, and your team and everything for putting it all together. Jake and Chloe, they're going to let you know when we're going to release the episode and we'll put clips and I'll connect to you on LinkedIn so we can post and be like, look at this awesome professional advice from Chris.

(Chris Slowe at 00:48:34) Sounds great.

(Joel Beasley at 00:48:35) Awesome, man. Have a fantastic day. And the next time I'm out in SF, I'll let you know and maybe we can hang out, grab a bite or tea or something.

(Chris Slowe at 00:48:43) Yeah. At least I can show you the office and give you some swag.

(Joel Beasley at 00:48:47) Show me the city.

(Chris Slowe at 00:48:48) Show you the city.

(Joel Beasley at 00:48:49) Yeah. And my time machine.

(Chris Slowe at 00:48:50) And my time machine.

(Joel Beasley at 00:48:52) Oh, come on, Musk. Don't get me excited about that. I want to meet the superheroes, though. Definitely want to meet the superheroes. Alright, buddy. You have a fantastic day. I'll talk with you soon.

(Chris Slowe at 00:49:06) Sounds good. Bye.

(Joel Beasley at 00:49:07) See you, bud. Thank you so much for listening. If you'd like to help, please take a moment right now to open up the iTunes app and leave a review of the podcast. If you take a screenshot of the review and text it or email it to a friend who needs to listen to the podcast and then CC me, [email protected]. If you CC me on the email, I'll send you a copy of the Modern CTO book or give you a shout out on the podcast, whichever you prefer.