343: Opt-In To Oversharing
Episode 343 · June 21st, 2022 · 30 mins 31 secs
About this Episode
Chris is weathering through a slight lull, a holding period, where his team waits for new features to become available with some of the platforms they integrate with, and as they think out new facets of the platform they're building.
Steph has been thinking recently about working in isolation. It's a topic that Joël Quenneville pointed out to her and mentioned. Can engineers work in isolation and be successful?
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CHRIS: Always be singing.
STEPH: I can't remember if I've shared the story with you. But I had a beautiful little human moment with someone at airport security. Because when I travel with my mic, I always get stopped because there's the middle long, thin piece that looks like what you would screw on to a gun like for a silencer. And so [laughs] as he was going through, the person was looking at it, and then he called over a buddy. And then they called over another buddy, and there's like three TSA agents all looking at the X-ray screen. And finally, they're like, "Yeah, we need to flag it." So they moved it over.
And then he was digging through, and he pulled out the big metal piece. And I said, "It's for a microphone." And he's like, "Okay," and he kept looking, and then he finally found the microphone. And he lit up because I guess he wasn't really sure to believe me at first when I said it. But he lit up, and he was like, "Karaoke?" [laughs] I was like, "No, it's for podcasting."
CHRIS: But not 100% no because we do sing plenty on this show, so...
STEPH: I think that's what made me think of it. It was your singing. [laughs]
CHRIS: Yep. My wonderful, wonderful singing.
STEPH: Hello and welcome to another episode of The Bike Shed, a weekly Podcast from your friends at thoughtbot about developing great software. I'm Steph Viccari.
CHRIS: And I'm Chris Toomey.
STEPH: And together, we're here to share a bit of what we've learned along the way. So, hey, Chris? What's new in your world?
CHRIS: What's new in my world? We are in sort of a...what's the word? There's a bit of a lull right now, not like a big lull, but we had a bunch of clear work that came into the team, did a bunch of iterations, some testing, built some new features, et cetera. And now there's a small holding period basically where we wait for some new features to become available with some of the platforms that we integrate with and also as we think out some new facets of the platform that we're building.
So we've got this little bit of time here where we're not necessarily building out as many new novel features. But instead, as a dev team, we're taking this moment to be like, oh, cool, let's tie down. I want to make a sailing analogy here, but I don't know sailing. It's like tie down the somethings and batten the hatches, maybe. That sounds like a thing. [chuckles] But so we have a couple of projects going right now. We want to really accept the truth and lean into Sidekiq. So right now, we have a mix of ActiveJob and Sidekiq jobs. And they're confusing, and et cetera, et cetera.
So we want to kind of lean into that, upgrade dependencies, that sort of thing. We are, again, doing a little bit of work on the observability foundation of our system. so how do we know what's going on at runtime? Also, working on just some core features and functionality. We have done a little bit of an exploration into the event processing stuff, some of that that I've been talking about. It's actually been very interesting. So we're working with Customer.io as a platform, which is omnichannel communication behavior-based messaging sort of thing. So when a user does X, send them an email and then wait three days. And if they haven't responded, then do this other thing.
And I think I've said this in previous episodes; I'm so wildly impressed with that platform. They have done such a good job. And I know that good software doesn't happen in a vacuum. In fact, if we're being honest, a lot of the software out there is not very good. And not only do they do a good job, but it's across...there's a ton of functionality in Customer.io.
And it's interesting because we're finding ourselves leaning into it even more because it is such a solid platform and because it connects into our event system. Like, it's a segment destination, so all of our analytics events get piped into Customer.io, and then we can action on any of them. And the actions can be quite complicated.
And this is where we're getting into good idea, terrible idea space. And to be clear, this is still just an exploration. But we basically wanted a way to do more. There are a bunch of different actions that you can take so, like send an email, send an SMS, or there are a couple of other slightly fancier ones. You can trigger an event within the Customer.io system. You can actually do an arbitrary HTTP POST, PUT, PATCH, whatever, any web requests you want to make. So if you want to integrate with essentially anything else out there, you can do that. You can send some structured data over the wire.
And so we've now been like, okay, what if, and stay with me here, what if we use our analytic system and we send events whenever a user does something, and then that event eventually trickles down to Customer.io? Within that, we allow ourselves to respond to that event by emitting a different event within the system, within Customer.io. And then, via the webhook functionality, we fire that back to the Rails application. And then there we can do whatever we want.
And in a way, that sounds absurd because we're starting from our app, and then we're sending some events down, processing them in certain ways, sending it back to the app, and then maybe doing something. In particular, one of the things we want to do is richly formatted Slack alerts. And Customer.io has a Slack alert functionality, but they can't have any of the fancy stuff. They can't link to our customer in the admin dashboard. So we found that that functionality is particularly useful for our admin team. And so we're like, ah, this feels weird.
But if we were to do this loop out and back, then ideally, we get the power of Customer.io for non-technical users or non-engineering team users to configure workflows and to say, "When a user does this, I actually want to alert the admin team via Slack." And we want it to be rich and have buttons that you can click and all that kind of stuff. And although the thing that I just described seems complicated, is a word that I'll use for it, confusing at times, it isn't...like, I don't want to do all of that in the app.
I don't want the app to have to think about how do I wait three days? We technically can do that with Sidekiq, but it gets us in trouble and whatnot, whereas Customer.io that's a core concept for them. And so, again, very much exploration. This will probably be a future good idea, terrible idea segment. But that's been an interesting one to explore.
STEPH: You have quite a talent for you preface something as a bad idea, and you do a very good job of making it sound reasonable and good. [laughs] So it's interesting to be on that side of like, good idea, bad idea. It's like, I'm looking for the bad. And I have questions, but overall, [chuckles] you do a very good job of being very thoughtful and walking through why it makes sense or what are the benefits of it. So you answered some of my questions around why still send it to Customer.io versus just having it all in-house. So the fact that the admin team has access to it makes a lot of sense.
I want to clarify one point. So when you send it to Customer.io, Customer.io then needs to send a message back to your application. And then that's when you customize the Slack message. Do you need Customer.io to send that message, or could you just fire off an event to Customer.io to say, "Hey, capture this, but don't do anything with this. And then we're going to send the Slack message because we want to customize it."?
CHRIS: I think the key is that we want to leverage the fact that Customer.io is the platform that our operations team really is now becoming comfortable with and using for this behavioral automation workflow type logic. So that idea of when this event, you know, when this triggering event happens, if this condition is true, then respond in this way.
And so because Customer.io is the platform that A, is quite good at that and B, is where our admin team is now thinking about doing that, one thing that we might do let's say a user completes some action within the application. So they fill out a form to submit their interest in some new platform feature. Initially, what we might want to do there is alert ourselves to say, "Hey, this happened. Take some action." And then eventually, we may want to instead switch that over and send an email to the customer with the next steps that they need to do.
And the ability to gradually transition across that spectrum is really interesting to me, and again, Customer.io being the platform, sort of the hub for how we respond to these events. At the same time, I know that this feels like a generic message processing system that might be a Kafka queue somewhere else. And so I've got that in the back of my head of like, is this weird? I think it's a little weird. But it also, thus far as we're exploring it, is very approachable for the admin team, very familiar for them, and reasonably powerful.
And also, there's a drag and drop editor for the events and the payloads. And it knows for this event, here's the stuff that's available to you. And so the ability for our admin team to interact with that interface is really great. And we don't have to build it. We don't have to think about it. But I will say I've worked at so many different companies that have their ad hoc system that makes it easy to do generic X, Y, and Z. And it's bad, and it falls down. And it's impossible to know when anything happens.
And so, I've got a lot of concerns in the back of my head, which I will want to at least think through and understand the trade-offs that we're making if we pursue this path, but it is very interesting to me. So right now, a lot of this logic does live in the app. But it means that it requires a code change for anything that we want to do like this. We want to have a Slack alert whenever X happens. Now, the developers are in the loop for all of that. And really, it's the operations team that owns the decisioning on that.
And so if they can also self-serve and instrument the action, the alert, the follow-up, the whatever it is, if we can give them those primitives in a platform that they already understand, that sounds nice. I'm intrigued, is what I'll say. So anyway, while we're in this lull period, we are trying out some fun stuff like that and exploring those sorts of things.
STEPH: I like that perspective that you're putting on it, or at least the one that's standing out to me is the concept of ownership is like who gets to own these actions. But then beyond that, that's the part where I feel a little squirmy is, so we are using this third-party tool because it makes life easier. But then, at what point when we start building software around this third-party tool to then customize it back on our own side. Then if someone is in Customer.io, so if an admin user is in there and then they trigger an event, is there going to be confusion as to what's going to happen? And can they retry an event?
Because I'm realizing my initial suggestion where it was like, hey, notify Customer.io that this is there but then also manage sending the Slack message that would prevent them from being able to have that retry capability. And that may be very much worth preserving. So then it's understood that hey, if you want to manage this, we are giving you full access to manage this work. We may customize it, but this is still the interface in which you go through to have three tries or to manage that workflow or these actions that get sent to users.
CHRIS: Yeah. I think you've perfectly highlighted the why this might not be a great idea or at least the concerns to explore before adopting this more thoroughly. And even just the idea of adopting it more thoroughly, like, how tied into the system are we? How business-critical does this new external piece of software become? Because I've seen that to be really problematic where there are organizations that I've worked with that are like, "Oh God, we would love to move off of system X. But unfortunately, it's basically the one thing holding this business up." And I'm like, yeah, I get that. And that happens. So yeah, being really intentional with that.
And that's why we're very much in an exploration place. But we have a bunch of stuff that we've done that required engineering work. And we're now seeing like, actually, could we map this into this other tool? And can we build the set of primitives in that space that now this team can own that whole experience? And then critically, can they debug it? Will we know when something goes wrong, et cetera? Those are always parts. At this point, I don't think I can just imagine a happy path. And I hope this isn't true for the rest of my life.
But the work as a software developer, especially after having done a couple of rounds of it and as a consultant, I just imagine failure modes. It's all I do. I'll be like, okay, we just need to wire X up to Z, and then we need to fire off a request. And then, once we get the message back, then we can process them. I'm like, right. You just described 13 things that can go wrong. Now let's imagine each of the different failure states because that's all I'm going to do.
Who cares about the happy path? Those are easy. Those write themselves. It's all of the failure modes that I need to think about. And someday, when I retire, and I go to a log cabin in the woods, and I don't talk to people for a while, maybe I'll go back to a place of only happy paths. But that is not my truth right now.
STEPH: I can't tell you how many people in my personal life I have annoyed so much [laughs] because all I see are failure modes. And one, that's a delightful t-shirt. [laughs] I'd love to have that. And then yeah, I feel you because there are so many times where someone is...like, I'm with someone who's like a big idea person. And so they're just launching into what-ifs, and we did this. And I can't help it, and I have learned to help it.
But it has been a struggle with some strong feedback from family and friends to reel it in. Because then I will start to think through okay, well, what's the details? And I have some questions. What happens when this happens? And yeah, all I see are failure modes. [laughs] It is very true for me too, and not always...not so great. So I, too, shall get a log cabin one day and try to forget all of that.
CHRIS: I will say I painted that as a particularly glib version of myself. But some of what I'm doing right now, particularly joining an early-stage startup and taking the role of CTO, was very much to try and intentionally resist that. Because right now, I have to be really careful with how much of the potential edge cases and whatnot. I'm considering exactly how robust of a platform are we building? Very is the answer. But what about extremely? Because extremely is an option but extremely costs four times as much. Mostly in time being the critical element there.
And so part of the work that I'm doing now is just trying to push on those edges, push on those boundaries, find the places where we can move quickly, and still build a robust platform because frankly, we're building...Sagewell is a financial platform under the hood, and I can't be flippant with that. We as a team have to be really careful with the thing that we're building. But we also have to move quickly.
We have to be able to iterate. We have to be able to build something and try it out and see if it works. And then, if it doesn't, maybe shelve it and pull it out of the codebase. And it has been a real challenge, but it was the challenge that I wanted here. And so I've been enjoying that work, but it has been a stretch, a growth moment, let's call it.
STEPH: I don't know if you've shared that particular goal with me in transitioning to a CTO role, but I really, really like it. One, it's very aligned with who you are. You're very thoughtful, and you look for areas to push and ways to do that. And then I also struggle in those areas, and thoughtbot specifically and consulting has helped push me in directions, push me out of my comfort zones but still in a safe space where I have other people to talk to as I'm making those decisions and pushing past the comfort areas that I have.
But one of them is that I will initially think things have to be perfect or really planned. And I had a really nice conversation with Chad Pytel, who is one of the Founders of thoughtbot and also COO and host of the Giant Robots Smashing Into Other Giant Robots Podcast. And we were chatting about a new offering that thoughtbot is bringing to the market. And it's one that I've been involved with. And I started getting really in the weeds of like, but we really have to plan out how this is going to look and all the actions that need to take place before then we can really sell this type of engagement to a new client.
And as I was going through this list of worries, when I was done, he mentioned he's like, "All of those are valid and something to consider." He's like, "But we don't have any customers yet." So the first part is we feel that we are in a space that we have enough of information to get started. And it's something that we've done before. And then, we'd like to see where customers align with us on this need because we're going to end up shaping this work in response to what their needs are. And so, we can't really begin that shaping until we understand more of what people are looking for.
I was like, oh yeah, that's such a nice point. It just reminded me in regard to pushing those boundaries of yes, we need planning upfront, and we look for failure modes. But then there's also an important aspect of then finding ways to keep moving forward and getting more feedback and then balancing those two.
CHRIS: Yeah, I think that's definitely right the as always, anchoring it to the customer. What is it that they need? How do we connect with them and hear from them? And ideally, keep those feedback loops as short as possible. That's the game, and everything else fits around that. But yeah, so we're trying some stuff. We'll see how it goes. I will certainly report back, depending on how it plays out. But that's a little bit of what's up in my world. What's up in your world?
STEPH: I have been thinking recently about working in isolation. It's a topic that Joël Quenneville, who's another thoughtboter and has been on the show a number of times, it was a topic that he'd actually pointed out to me and mentioned. And so, I wanted to bring that here and share it with you because I'd love to get some of your thoughts on this as well. But I've typically had the viewpoint that when developers are sent off to work on a large, nebulous task, that it's a recipe for disaster, and almost everyone's going to lose in that scenario. And it tends to be a combination of isolation, very distant due dates, and loosely defined scope that leads to those really poor results.
However, as developers, it's not inconceivable for us to land in that position. And it's very similar to my current project, who I'm working with Joël on, where we were given a very fuzzy project with some really aggressive goals, and the engagement is going really well. So that led Joël and I to wonder why is this working? This is the thing that we said that people should never do, but it's actually going quite well for us.
So reflecting upon some of the things that are working well for us, even though we are in more of an isolated state than we would typically work, some of the things that I've been reflecting on or some of the strategies I should say that we've applied to this situation is number one, we did work hard to plug into an existing team. So when we joined, we joined more of an ad hoc volunteer team.
And in everybody's spare time, those individuals were then contributing to the CI process in terms of trying to speed things up and improve things for the rest of the team. But otherwise, there wasn't really a team. There wasn't much structure to it. So it felt like everybody was very much off in their own world doing their own thing, occasionally putting up some code changes for review. And then you had to gain a lot of context to understand what it was that they were doing.
So one of the things that I advocated for early on that I thought was more of just my personal preference but I think has actually worked well in regards to the success of the project as well is to plug into an existing team. So even if you are not working with that team on their day-to-day tasks, but you want to have more people to interact with and more people to share your context with. So you are essentially reducing the isolation of you're no longer these two people who are off in a corner working on something, and nobody has any idea what you're doing, and only one person is getting a status update.
There is now a whole channel or team of people that have some insight as to what's going on. And they can also really unblock you for when you get stuck because then if you do have a question, but there's that one person who has been like your go-to person for this whole project, if they're out on vacation, or if they leave, or just something happens, you're suddenly blocked.
And you don't know who to go to because you've been part of this larger company, but you haven't interacted with anybody outside of that one person. So at least if you're plugged into another team, you've immediately got some friends or some other people to go to and say, "Hey, I'm not sure who can help me with this, but I have this problem." And then, from there, you can get more help.
CHRIS: This is super interesting. To start, I really like that you're framing this in terms of this is a thing that we often recommend against or see as an anti-pattern, and yet in this particular case, it's working. Let's look at that. Because I think the things that you're like, huh, that's interesting. That phrase "Huh, that's interesting" is very interesting. It often highlights like oh, something is behaving counter to how we would expect it to, so let's dig in and explore that. And so I love that that was the reaction and then sort of the conversation that spilled out of that.
I'm also not super surprised that the combination of you and Joël were able to find a way to make this successful because you are two of the most capable developers that I've worked with but also particularly excellent communicators and advocates for the work that you're doing and the way that one should do the work. So the idea that there's a situation that may not be the ideal mode of working and that you're able to take that and say, "What if we shift it just a little bit and make it a little bit more manageable and whatnot?" So unsurprised, frankly, that you found a way collectively to make this a little bit better.
And then I think yeah, it sounds like you're doing the things...so just like, we're in isolation, hmm, that doesn't seem great. Let's unisolate and connect to some people, and that just feels so true. I'm very interested to hear, though. I'm guessing there's more to this story or other things that you've done. Are there other tactics or ways that you've shifted this around?
STEPH: Yeah, there's a couple more. So this is one that (And thank you for the kind words.) this was one that I think Joël is really exceptional at. So Joël is really good at building diagrams and graphs and then sharing that with the team as sort of like we've spent a couple of days understanding this big, messy concept. Here's a nice condensed graph that shows how we went about understanding this. And then here's the big overall picture of what we've learned from this, which has been wonderful for so many reasons.
And every time that we share something with the team, one, it just helps build camaraderie, especially in remote days, it just builds camaraderie on hey, we're all online. And we're working. And here's the thing that I'm working through or struggling with or something that I learned. I often do that, especially when I get frustrated and something goes wrong. I love to share the I did this today. It went terribly. [laughs] Let me tell you about it, so you're aware of it in case it helps you.
And specifically, the diagrams are really nice because then other people can just see and appreciate it, or they can point something out that we didn't know. Or they'll see a different angle because they're more familiar with the system. So they can say, "Oh yeah, that totally makes sense," or "I had no idea that was happening." So that's been a really nice way to engage with the team.
And so, essentially, the little title for that strategy is just overshare. Just share all the things that you're doing and find ways to make it digestible for the team so then they can go along on this big, nebulous journey with you. And you can also put it in threads so that way, you're not flooding a channel, but then people can opt-in to that oversharing if they would like more insight into the work that you're doing.
CHRIS: Opt-in to that oversharing. [laughs]
STEPH: Exactly. I mean, it's not forced oversharing; it's just it's here if people would like it. That was a really nice compliment that some other thoughtboters received from their client team is someone had mentioned that there's so much information that's getting shared from the thoughtboters that they had trouble keeping up. And they really liked that. They really appreciated that they could then go check out this channel or these threads and see exactly the type of work that was happening and the outcomes of it. And then they could just check it maybe beginning of the day, end of the day and get that knowledge dump.
Some of the other strategies that we've used are giving ourselves mini-goals to accomplish as part of the larger, more nebulous task. So as we have this very large goal in mind, it's like, where's the small piece? Where's an entry point? What's a task or a goal that we can define? And then we want to break that down into what questions do we need to ask? How can we start moving in this direction? And we want to find something that has an answer.
So each time that we start researching once we've gotten to that point...and this is hard. I feel like people may know that, but I should just say that this is hard to take something nebulous and then find the entry point and break down some goals. And that has been one of the wonderful parts of then having a buddy for this type of project because then we can bounce ideas off of each other.
And we can also help the other person not go too deep into an area. Because I have definitely had moments where I've been very passionate about like, "We need to do this," and Joël is just like, do we? And I'm like, "Yeah." And he's like, "Do we though?" And I'm like, "I guess not. I just really, really want to." [laughs] It's been very helpful to have a partner balance some of those feelings.
And once you can break down some of that amorphous problem into those smaller goals, then you can also create tickets, which is also a really nice way to then surface the work that you're doing. You can document how you're researching, document the question. And then once you have that question of what you're in search of, it's so nice because then once you find the answer, that's immediately a good moment to pause and reflect.
So I think in a recent episode, we were chatting about this where Joël and I were trying to understand why the tests weren't being balanced properly across each process that was available. And we found the answer, and we started immediately digging into fixing it or solutions. And then it took us a moment to go back and say, "Actually, this ticket is really just about understanding the problem, not fixing the problem." And so that was a nice; now that we understand the problem, let's go back high-level to define our next goal from this big, nebulous task because maybe fixing that balancing is the right thing to do, but maybe not, and we just need to reconsider.
So for that portion of breaking down a big, nebulous task and then identifying smaller tasks that you can achieve, time-boxing has been huge for us in regards of what’s something that we can accomplish this week, or what's something we can accomplish today that will then move us forward? And then making sure that we are setting deadlines for ourselves. So normally, this is another area where it's like, huh, that's interesting. I'm a big believer in deadlines. But I do think self-imposed deadlines are really helpful.
CHRIS: I'm intrigued to hear you say that you're not a big fan of deadlines because I assume we're actually more aligned on this. But deadlines that are arbitrary and also come with fixed scope and other immovable things, yes, those are the worst in the world. But deadlines that we set for ourselves, and then we use that as a mechanism to hone and refine the scope that we're going to get out the door by that deadline, I find those incredibly useful. And that sounds like that's the same sort of thing you have going on here is like by saying we're willing to expend this much to get a result, that defines the work going into it.
STEPH: Yeah, that's fair. Everything that you said is true, too; in regards to, I'm realizing I default that when I hear the word deadline, I'm so used to teams having deadlines that are defined by other individuals that are not part of the work. And as you said, the scope has already been defined, and it can't be changed. And it's all of the bad things that then go with it.
So when I think of deadlines, I immediately think of that type of deadline versus the more self-imposed, yes, we can revisit, yes, the team has bought in and understands why this is important. Those types of deadlines are very helpful. It's that first part that I default to that I think of immediately, and I need some reassurance that that is not the type of deadline that I'm looking at or being forced to meet.
I have a very similar feeling for estimates. Like, those both fall in the same category for me is; as soon as I hear estimation and deadline, I get nervous. And then I just need to understand the purpose of both and who is setting both of those and the communication around them. And then what does that failure mode look like, the one that we're always looking for? So yeah, deadlines and estimations fit into that. Initially, I'm very hesitant and cautious, but I think they're both very good tools.
CHRIS: Yeah, I feel like those are very closely related. And they're definitely tools that can be used for great good or for great evil. And so, ideally, we advocate for the great good usage. But more generally, I love, again, the sharing around the process and what's worked for you in this less typical or often somewhat problematic workflow. I will say, again, so I gave you the series of compliments earlier, and I stand by those compliments for you and Joël.
But I think also the sort of related aspect is that you two are both quite senior, very capable, very comfortable suggesting changes, suggesting workflows. So I think the potential dangers of isolation are still very much there. And the fact that the two of you have been able to find a way to work more effectively and perhaps change the terms of things just a little bit to make this effective is A, unsurprising but B, not something that I would expect of every team.
I think you've described a wonderful list of the specifics as to how you did that. And ideally, if folks that are perhaps a little earlier on in their career are sent out for a month with a wild project, and they're sent to do it in isolation, hopefully, they can borrow from that list. But again, I do think this is a thing that, from an organizational perspective, we should be very careful with when we're imposing this isolation on it because it takes two fantastic folks like you and Joël to break out of the shackles of it.
STEPH: The more we're talking about this, the more apparent it's also becoming that I started with this; how do you manage isolation? And my answer is you get out of it. [laughs] Get out of isolation as quickly as possible. Someone thought it was a good idea to put you there or a good idea to structure it that way. Or maybe they didn't mean it intentionally, but that's how things then shook out. So that's really what a lot of those strategies are about is, then how do I get myself out of this corner that you put me in? Because nobody put Stephanie in a corner.
So it's essentially that's all the strategies are looking for ways to say, hey, I'm isolated, but I really don't want to be, and it's dangerous for me to be isolated in this way. Even as a more senior capable developer, it's more likely that things could go wrong, and miscommunications, misaligned expectations. So I need to find ways to then bring the work that I'm doing to make it more relevant to other people on the team. So then we can have more overlap, or at least I can share a lot of the work that's being done.
CHRIS: Yeah, absolutely. I think with that wonderful summary and, frankly, utterly fantastic movie reference, what do you think? Should we wrap up?
STEPH: Let's do it. Let's wrap up.
CHRIS: The show notes for this episode can be found at bikeshed.fm.
STEPH: This show is produced and edited by Mandy Moore.
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STEPH: If you have any feedback for this or any of our other episodes, you can reach us at @_bikeshed or reach me on Twitter @SViccari.
CHRIS: And I'm @christoomey.
STEPH: Or you can reach us at email@example.com via email.
CHRIS: Thanks so much for listening to The Bike Shed, and we'll see you next week.
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