TECH TITANS: The Power of Big Decisions with Chris Slowe, CTO & Founding Engineer at Reddit

(Intro Narrator at 00:00:00) Today, we're bringing you an episode of Tech Titans. Chris, the CTO of Reddit, joins us in this episode to share his best advice and how he thinks through big decisions as a leader. You're listening to Joel Beasley, Tech Titans.

(Joel Beasley at 00:00:18) First question, how do you do one-on-ones? What's the cadence? How do you approach that?

(Chris at 00:00:23) Okay. So I think for having had a lot of different hats over the last five years, I'd varied a little bit by level. But I'd say that one-on-ones, it depends on the level of person you're doing one-on-ones with. I think when back when I was an engineering manager, my general rule of thumb was I would do bi-weeklies with all of my 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-required doc.

(Chris at 00:00:59) I like having a place to refer to for what we're going to talk about, and it's only because it enforces a certain amount of structure on the discussion. You know, it means you can do things like say every four weeks we're going to talk about your professional development, which is something that I think is easy to let 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 ways to make progress. And so I've gotten very much into that approach of let's have a doc, the good, the bad, and just miscellaneous topics. And I think, you know, as I with more senior talent, with directors, there's a section that also involves OKRs specifically in the one-on-one doc.

(Chris at 00:01:44) Not because 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 at 00:02:09) 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 is 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 of it.

(Chris at 00:02:46) 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. 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. I think, you know, I'm sure that one of the things you hear the most is just getting candid feedback is just the hardest, most valuable thing you can get. And it kind of goes back to the humility part.

(Chris at 00:03:11) 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. 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. It doesn't have to be always constructive feedback. I mean, literally, it is actually good to hear stuff that's going right.

(Joel Beasley at 00:03:41) Yeah. I actually had one of those today. You know how you told me about designers? Right? Well, we had a designer start about three weeks ago, Pam.

(Joel Beasley at 00:03:52) And she's straight killing it. She's doing so good. And I did that thing where I had an idea, 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 hers. And I was like, just thank you.

(Joel Beasley at 00:04:07) Thank you so much because that means you can self-organize, and I can just keep feeding you stuff, and you can organize it. I don't have to worry about having a special "Pam, don't tell her this now" list and all this stuff. And yeah. So I was that's amazing. I'm super glad that you have that skill. And so that was my feedback with her today.

(Chris at 00:04:27) Yeah. And, you know, it is really easy to just kind of dwell on the problems and not really take the wins. You do have to actually recognize people for the good stuff, and it's kind of important.

(Joel Beasley at 00:04:39) You make a lot of big decisions. What advice do you have in the decision-making space? What's some of your good nuggets of knowledge there?

(Chris at 00:04:45) 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?

(Chris at 00:05:07) 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 it's okay for them to do that.

(Chris at 00:05:47) Or at least, you know, they just need to talk it out and convince themselves they're right and commit 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, go do it. It's not because I'm just saying that I don't have an opinion in the matter. It's I'm saying that your opinion is probably more informed than mine and why aren't you even talking? Go do it.

(Chris at 00:06:07) And it is, of course, it varies a lot by, it varies by experience. It varies by level. I mean, I have the luxury of having a bunch, you know, very senior leadership also reporting to me. I think when it comes down to, you know, rank and file, we'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 become experts at their job and therefore be allowed to make decisions and not feel like they're going to be honored. 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. Yeah, this sounds like a really good idea. Is it a now kind of idea or, you know, how does it compare to these other 30 things that you need to do?

(Chris at 00:06:50) And if you tell me it's number one, then we can have that debate, then, yeah, let's 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. Or why I want to deprioritize it in some cases.

(Joel Beasley at 00:07:05) 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? You're welding. You're studying. You've got the belt on, the pliers. You're welding at Harvard.

(Joel Beasley at 00:07:20) You can go back to this exact moment, and you can gently whisper some advice into your ear. And that's it. That's it. Just this little whisper of advice. What would it be?

(Chris at 00:07:31) Oh, that's a tough one. So this is going to slowly wreck my, well, so going back to my career feels like it was a series of fortuitous events that kind of accumulated into two results. How much of the card castle am I destroying by whispering something to myself? I mean, my joke answer would be probably, buy Bitcoin in 2009. Right?

(Chris at 00:07:58) It's straight up this will fix everything. I think, oh, God. That's a tough one. I think a lot of the stuff that's been most valuable has been by experience and the actual, maybe that's the main advice is that the journey is kind of the point. Right?

(Chris at 00:08:17) The destination is less important than the journey, because I think that, especially getting into my own head in grad school, I was all about, yeah. If I get my degree, then I can start working on my postdoc, and then I'll work on getting a professorship and these big milestones and a layout for yourself. When in actuality, life's a heck of a lot more complicated than a bunch of milestones that you end up making for yourself. So I'll stick with that one. I'll say it's about the journey, not the destination.

(Joel Beasley at 00:08:43) I love it. And it's good. And it's true. Right? It's a great piece. But you did bring up a question in my mind. It's like the, 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? I mean,

(Chris at 00:09:04) 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 the, I'd say to answer your question directly, yes. I think that having a destination in mind is always important because otherwise, you can go, what is the point? And it kind of comes back to one thing we bring up a lot here has been this potentially totally false anecdote about NASA in the '60s where, you know, all of NASA was set up in the '60s to be about putting a man on the moon. 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 cleaning the floor, what is your, what are you doing here?

(Chris at 00:09:51) 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 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. Right?

(Chris at 00:10:12) Sometimes a goal is a means to a better goal, and you just don't have the insight to figure out you're going in the wrong direction.