338: Meticulously Wrong

Episode 338 · May 17th, 2022 · 45 mins 52 secs

About this Episode

Chris switched from Trello over to Linear for product management and talks about prioritizing backlogs.

Steph shares and discusses a tweet from Curtis Einsmann that super resonated with the work she's doing right now: "In software engineering, rabbit holes are inevitable. You will research libraries and not use them. You'll write code just to delete it. This isn't a waste; sometimes, you need to go down a few wrong paths to get to the right one."

This episode is brought to you by BuildPulse. Start your 14-day free trial of BuildPulse today.

Curtis Einsmann Tweet
Louie Bacaj Tweet

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CHRIS: Good morning, and welcome to Tech Talk with Steph and Chris. Today at the top of the hour, it's tech traffic hits.

STEPH: Ooh, tech traffic. [laughs] I like that statement.

CHRIS: Yeah. The Git lanes are clogged up with...I don't know. I got nothing.

STEPH: [laughs]

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? Actually, I have a specific new thing that I can share, which is, as of the past week, I would say, switched from Trello over to Linear for product management. It's been great. It was a super straightforward transfer. They actually had an importer. We lost some of the comment threads on the Trello cards. But that was easy enough to like each Linear ticket has a link back to Trello. So it's easy enough to keep the continuity.

But yeah, we're in a whole new world, a system actually built for maintaining a product backlog, and, man, it shows. Trello was a bunch of lists and cards and stuff that you could link between, which was cool. But Linear is just much more purpose-built and already very, very nice. And we're very happy with the switch.

STEPH: I feel like you came in real casual with that news, but that is big news, that you did a switch.


CHRIS: How are you going to bury the lead like that? You switched project management...[laughter] I actually didn't think it was...I'm excited about it but low-key excited, which is weird because I do like productivity and task management software. So you would think I would be really excited about this. But I've also tried enough of them historically to know that that's never going to be the thing that actually makes or breaks your team's productivity. It can make things worse, but it can't make you great. That's the thing that I believe. And so it's a wonderful piece of software. I'm very excited about it but --

STEPH: Ooh, I like that. It can make you worse, but it doesn't make you great. That's so true, yeah, where it causes pain. Well, and it does make sense. You've been complaining a bit about the whole login with Trello and how that's been frustrating. But I haven't even heard of Linear. That's just...that's, I mean, you're just doing what you do where you bring that new-new. I haven't heard of Linear before.

CHRIS: I try to live on the cutting edge. Actually, I deeply try to not live on the cutting edge at this point in my life. That early adopter wave, no, no, no, that's not for me anymore. But I've known a few folks who've moved to Linear. And everyone that I've spoken to who has moved to it has been like, "Yeah, it's been great." I've not heard anything negative. And I've heard or experienced negative things about every other product management tool out there. And so, it seemed like an easy thing.

And it was a low-cost enough switch in terms of opportunity costs or the like, it took the effort of someone on our team moving those cards over and setting up the new system and training, but it was relatively straightforward. And yeah, we're super happy with it. And it feels different now. I feel like I can see the work in a different way which is interesting.

I think we had brought in a Chrome extension for Trello. I think it's like Hello Epics or something like that that allows...it abuses the card linking functionality in Trello and repurchases that feature as an epic management thing. But it's quarter-baked is how I would describe it, or it's clearly built on top of existing things that were not intended to be used exactly in that way. So it does a great job. Hello Epics does a great job of trying to make something like parent-child list management stuff happen in Trello. But it's always going feel like an afterthought, a secondary feature, something that's bolted on.

Whereas in Linear, it's like, no, no, we absolutely have the idea of projects, of course, and you can see burndown charts and things. And the thing that I do want to be careful about is not leaning too much into management. Linear has the idea of cycles or sprints, as many other folks think of them, or iterations or whatever you want to call them. But we've largely not been working in that mode. We've just continued to work through the next up list; that's it. The next up list should be prioritized and well defined at the top and roughly in priority order. So just pick up the next card and work on it. And we just do that every single day.

And now we're in a piece of software that has the idea of cycles, and I'm like, oh, this is vaguely interesting. Do we want to do that? Oh, but if you're going to do that, you probably do some estimation, right? And I was like, oh no, now we're into a place that's...okay, I have feelings. I got to decide how to approach that. And so, I am intrigued. And I wonder if we could just say like ten carts that's how many come into a cycle, and that's it. And we use the loosest heuristics possible to define how we structure a cycle so that we don't fall into the trap of, oh, what's our roadmap going to look like six months from now? JK, what's anything going to look like six months from now? That's not a knowable fact.

STEPH: I was just thinking where you said that you're moving into sprints or cycles, and then there's that push, well, now you got to estimate. And I just thought, do you? Do you have to estimate? [laughs]

CHRIS: We need a burndown chart through 2024, and it must be meticulously accurate down to the hour.

STEPH: I think meticulously wrong is how that goes. [laughs]

CHRIS: Which is the best kind of wrong. If you're going to be wrong, be meticulous about it.

STEPH: Be thorough about it. [laughs] Yeah, the team that I'm on right now, we have our bi-weekly planning, and we go through the board, and we pull stuff in. But there's never a discussion about estimation. And I hadn't really appreciated that until just now. How we don't think about how long is this going to take? We just talked about, well, what's in-flight? And how much work do people still have going on? And then here's the list of things we can pull in. But there's always a list that you can go back to.

Like, it's very...we pull in the minimum and knowing that if we run out of work, there's another place to go where there's stuff that's organized. And I just love that cadence, that idea of like, let's not try to make guesses about the future; let's just have it lined up and ready for us to go when we're ready to pull it in. Although I know, that's also coming from a very developer's perspective, and there are product managers who are trying to communicate as to when features are going to get out into the world. So I get that there's a balance, but I still have strong feelings and hesitations around estimating work.

CHRIS: Well, I feel like there is a balance there. And so many things in history are like, well, this is an overcorrection against that, and that's an overcorrection against this. And the idea that we can estimate our work that far out into the future that's just obviously false to me based on every project I've ever worked on that has tried to do it. And it has always failed without question.

But critically, there is the necessity to sync up work and like, oh, marketing needs to plan the launch of this feature, and it's a critical one. What's it going to look like? When's it going to be ready? You know, we're trying to go for an event, it's not just know...we developers never estimate anything past the immediate moment where like, that's not acceptable. We got to find a middle ground here. But where that middle ground is, is interesting. And so, just operating in the sort of we do work as it comes up is the easiest thing because no one's lying about anything at that point.

But sometimes you got to make some guesses and make some estimations. And then it gets into the murky area of I believe with 75% confidence that in three weeks, we will have this feature ready. But to be clear, I said with 75% confidence that means one-quarter of the time; we will not be there at that date. What does that mean? What does that failure mode look like? Let's talk about that. And can you have honest, open, transparent, useful conversations there? That's the space that it becomes more subtle if you need to do that.

STEPH: You're reminding me of a conversation that I had with someone where they shared with me some very aggressive team goals. And it was a very friendly conversation. And they're like, "How do you feel about aggressive goals?" And I was like, "Well, it depends. How do you feel about aggressive failure?" Because then once I know where you stand there, then we can talk about aggressive goals. Now, if we're being aggressive, but then we fail to achieve that, and it's one of those, okay, we didn't meet the goal that we'd expected, but everything is fine, and it's not a big deal, then I am okay. Sure, let's shoot for the stars.

But if it's one of those, we are communicating these goals to the outside world, and it's going to become incredibly important that we meet these goals, and if we don't, then things are going to go on fire, people are going to be in trouble, and it's just going to be awful, then let's not set aggressive goals. Let's not box ourselves into a space where we are setting ourselves up to fail or feel pain in a meaningful way. I agree that estimations are important, especially in terms of you need to collaborate with other departments, and then also just to provide some sense of where the product is headed and when things may be released.

I think estimations then just become problematic when they do become definite, and they're based on so many unknowns, and then when I don't know is not an answer. So if someone asked, "What's your estimate for this?" And the very honest real answer is I don't know, like, we haven't done this type of work before, or these are all the unknowns, and then someone's like, "Well, let's just put an estimation of like two weeks on it," and they just sort of try to force-fit it into being what they want, then that's where it starts to just feel incredibly problematic.

CHRIS: Yeah, estimation is a very murky area that we could spend entire episodes talking about, and in fact, I think we have a handful of times. So with that, Linear has been great. We're going to see just how much or how little estimation we actually want to do. But it's been a very nice addition to the toolset. And I'll let you know as we deepen our usage of it what the experience is like, but that's the main thing that's new in my world. What's new in your world?

STEPH: Well, before we bounce over to my world, you said something that has intrigued me that has also made me start reflecting on some of the ways that I like to work. And you'd mentioned that you have this prioritized backlog that people are pulling tickets from. And I don't know exactly if there's a planning session or how that looks, but I have recognized that when I am working with a team, and we don't have any planning session, if everybody is just pulling from this backlog, that's being prioritized by someone on the team, that I find that a bit overwhelming.

Because the types of work being done can vary so drastically that I find I'm less able to help my colleagues or my teammates because I don't have the context for what they're working on. It surprises me. I'm like, oh, I didn't even know we're working on that feature, or I don't have the context for what's the problem that we're trying to solve here. And it makes it just a lot harder to review and then have conversations with them. And I get overwhelmed in that environment.

And I've recognized that about myself based on previous projects that were more similar to that versus if I'm on a project where the team does get together every so often, even if it's high level to be like, hey, here's the theme of the tickets that we're working on, or here's just some of the stuff, then I feel much more prepared for the work that is coming in and to be able to context switch and review. And yeah, so I've kind of learned that about myself. I'm curious, are you similar, or how does that work for you?

CHRIS: I'm definitely similar. And I think probably the team is closer to what you're describing. So we do have a planning session every week, just a quick 30-minute scan through the backlog, look at the things that are coming up and also the larger themes. Previously, Epics and Trello now projects and Linear. But talking about what are the bigger pieces of work that we're moving on, and then what are the individual tickets associated with that that we'll be expecting to work on in the next week? And just making sure that everyone has broad clarity around what that feature set is.

Also, we're a very small team at this point. Still, we're four people total, but one of the developers is on a break for a couple of weeks this summer. And so there are really only three of us that are driving on the code. And so, with three of us working on the projects, we try very intentionally to have significant overlap between the various...like, we don't want any one person to own any portion of things at this point. And so we're doing a good amount of pairing to cross-pollinate and make sure everyone's...not everyone's aware of everything, but at least one other person is sufficiently aware of everything between the three of us. And I think that's been working well.

I don't think we have any major gaps, save for the way that we're doing our mobile architecture that's largely managed by one of the developers on the team and a contractor that we're working with to help do a lot of the implementation. That's a known we chose to silo that thing. We've accepted the cost of that for now. And architecturally, the rest of us are aware of it, but we're not like in the Swift code writing anything because I don't know how to write Swift at this point. I'd love to learn it. I hear good things about the language.


So yeah, I think conceptually very similar to what you're describing of still want to have people be able to review. Like, I don't want to put up a PR and people be like, I don't know, that looks like code, I guess. I'm not sure what it does. Like, I want it to be very...I want us all to be roughly on the same page, and thus far, we are.

As the team grows, that will become trickier to maintain because there are just inherently probably more things that are moving, more different feature areas and surface area that we're tackling in any given week, or there are different ways to approach that. I know you've talked about having a limited number of themes for a given cycle, so that's an idea that can pop up. But that's something that we'll figure out as we get further. I think I'm happy with where we're at right now, so yeah, that's the story there.

STEPH: Okay, cool. Yeah, all of that resonates with me, and thinking about it a little more deeply in this moment, I'm realizing I think something you said helped me put this together where when I'm reviewing someone's change, I'm not necessarily just looking to see does your code work? I'm going to trust you that your code works. I may have thoughts about design and other things, but I really want to understand more what's the change to the product that we're making? What's the goal that we're looking to achieve? How are we measuring this?

And so if I don't have that context, that's what contributes to that feeling of like, hard context switching of not just context switching, but now I have to level myself up to then understand the problem that's being solved by this. Versus had I known some of the themes going into that particular cycle or sprint, I would have felt far more prepared for that review session versus having to then dig through all the data and/or tickets or talk to someone.

Well, switching back to what's going on in my world, I have a particular tweet that I want to share, and it's one that Joël Quenneville brought to my attention. And it just resonates so much with all the type of work that I'm doing right now. So I'm going to read the tweet, and then we'll link to it in the show notes as well. But it's from Curtis Einsmann, and Curtis wrote: "In software engineering, rabbit holes are inevitable. You will research libraries and not use them. You'll write code just to delete it. This isn't a waste; sometimes, you need to go down a few wrong paths to get to the right one."

And that describes all the work that I'm doing right now. It's a lot of exploratory, a lot of data-driven work, and finding ways that we can reduce the time that it takes to run RSpec on CI. And it also ties in nicely to one of the things that I think we talked about last week, where we discovered that a number of files have a high runtime variance. And I've really dug into the data there to understand, okay, is it always specific files that have these high runtime variants? Are there any obvious contributions to what's causing this? Are we making real network calls that then could sometimes take a long time to return? And the result is there's nothing obvious.

They're giant files. The number of SQL commands that are being run for each file varies drastically. They're all high, but it's still very different. There's no single fact about these files that has really been like, yes, this is what's causing these files to have such a runtime variance. And so while I've been in the data, I'm documenting it, and I'm making a list and putting it all together in a ticket so at least it's there to look at later. But I'm going to move on. It's one of those I would love to know what's causing this. I would love to address it because it would put us in an ideal state for how we're distributing tests, which would have a significant impact on our runtime.

But it also feels a little bit like chasing my tail because I'm worried, like with some of the other experiments that we've done in the past where we've addressed tentpoles, that as soon as you address the issue for one or two files, then other files start having the same problem. And you're just going to continue to chase and chase, and I don't want to be in that. So upfront, this was one of those; hey, let's look at the data. If there's something obvious, let's address it; if not, move on. So I'm at that point today where I'm wrapping up all of that data, and then I'm going to move on, move on to the next thing.

CHRIS: There's deep truth in that tweet that you shared at the start of this segment. The idea like if we knew the work that we had to do at the front, yeah, we would just do that, but often, we don't. And so, being able to not treat it as a failure when something doesn't work out is, I think, so critical. I think to expand on the idea just a tiny bit, the idea of the scientific method, failure is totally an option and is part of science.

I remember watching MythBusters, and Adam Savage is just kind of like, "Failure is always an option," and highlighting that as part of it. Like, it's an outcome. You've learned something. You have a new data point. You can take that and then carry it forward with you. But it's rough in the moment. And so, I do think that this is a worthwhile thing to meditate on. And it's something that I've had to revisit a handful of times in my career of just like, man, I feel like I've just been spinning my tires all week. I'm like, we know what we want to get done, but just each approach I take isn't working for one reason or another.

And then, finally, you get to the end. And then you've got this paragraph-long summary of all the things that didn't work in your PR and one-line change sort of thing. And those are painful, but they're part of the game. Like, that is unavoidable. I have not found a way to just know how to do the work upfront always. I would love that. I would sign up for whatever seminar was selling that. I wouldn't. I would know that that seminar is a lie, actually. But broadly, I'm intrigued by the idea if someone were selling that, I'd be like, well, I mean, pitch me on it. Tell me why I should believe you; I don't, just to be clear. But yeah.

STEPH: This project has really helped me embrace always setting a goal or a question upfront about what I'm wanting to achieve or what I'm looking to answer because a number of times while Joël and I have been spelunking through data...And then so originally, with the saga, we started out with why doesn’t our math match reality? We understand that if these tests are distributed perfectly across the CPUs, then that should cut the runtime in half. But yet, we weren't seeing that even though we had addressed the tentpoles.

So we dug into understanding why. And the answer is because they're not perfectly distributed, and it's because of the runtime variance. And that was a critical moment to look back and say, "Did we achieve the goal?" Yes, we identified the problem. But once you see a problem, it's just so easy to dig in and keep going. It's like, well, now I want to know what's causing these files to have a runtime variance.

But it's one of those we achieved our goal. We acknowledged upfront that we wanted to at least understand why. Let's make a second decision, do we keep going? And I'm at that point where, frankly, I probably dug in a little more than I should because I'm stubborn. But I'm recognizing that now's the time to back away and then go back and move on to the next high-priority item, which is converting for funsies; I'll share.

The next thing is converting Test::Unit test over to RSpec because we have, I think, around 25 tests that are written in Test::Unit. And we want to move them over to RSpec because that particular just step in the build process takes a good three to four minutes. And part of that is just booting up Rails and then running the tests very fast. And we're underutilizing the machine that's running them because it's only 25 tests, but there are 86 CPUs to run it.

So we'd really like to combine those 25 tests with the rest of the RSpec suite and drop that step. So then that should add minimal time to the overall build but then should take us down at least a couple of minutes. And then also makes it easier to manage and help folks so that way, there's one consistent testing framework that's in use versus having to manage some of these older tests.

CHRIS: It's funny; I think it was just two episodes back where we talked about why RSpec, and I think both of us were just like, well yeah. But I mean, if there are tests and another, like, it's fine, you just leave them with the exception that if there's like 2% of our tests are in Test::Unit, and everything else is in RSpec, yeah, maybe that that conversion efforts seem totally worth it.

But again, I think as you're describing that, what I'm hearing is just like the scientific method, just being somewhat structured in the approach to what's the hypothesis? And what's the procedure we're going to use to determine if that hypothesis is true or false? And then what do we do? And then what are the results? And then you just do that on loop. But being not just sort of exploring. Sometimes you have to be on exploratory mode. But I definitely find that that tiny bit of rigor of just like, wait, okay, before I actually do anything, what do I think is going on here? What's my guess?

And then, okay, if that guess were true, what would I be able to observe in the world? Okay, here we go. And just that tiny bit of structure is so...it sometimes feels highly formal to go into that mode and be like, no, no, no, let me take a step back. Let me write down my thoughts. I'm going to have a little checklist and do the thing. But I've never regretted doing it. I will say that. I have deeply regretted not doing it. I feel like I should make a list of things that fit that structure.

I've never regretted committing in Git ever. That's been great. I've always been able to unwind it, but I've never been able to not unwind it or the opposite. I've regretted not committing. I have not regretted committing. I have regretted not writing out my hypothesis or approach. I have not regretted doing it. And so, yeah, this feels like it falls firmly in that category of like, it's worth just a tiny bit of structure. There's a reason it is the scientific method.

STEPH: Yeah, I agree. I've not regretted documenting upfront what it is I look to achieve and how I think I'm going to answer the question. That has been immensely helpful. Because then I also forget, like, two weeks ago, I'll be like, wasn't there a question around why this was happening, and I need to understand? And all of that was so context-heavy that as soon as I'm out of the thick of it, I completely forget it. So if I care about it deeply or if I want to be able to revisit it, then I need to document it for myself.

It's given me a lot of empathy for people who do more scientific research around, oh my gosh, like, you have to document everything you do and then still be able to prove it five years from now or however long. I'm just throwing out numbers. And it needs to be organized enough that someone, if they do question your research that, then you have it there. My research documents would not withstand scrutiny at this point because they are still just more personal notes. But yes, it's given me a lot of empathy and respect for people who do run very serious research, experiments, and trials, and then have to be able to prove it to the world.

Pivoting just a bit, there's a particular topic that resonated with both you and I; in fact, it's a particular tweet. And, Louie, I do apologize if I mispronounce your last name, but Louie Bacaj. And we'll include a link in the show notes to the tweet, but Louis shared, "I managed multiple engineering teams before quitting tech. Now that I quit, I can speak freely. Here are 12 things your manager may not be telling you, but I know for a fact will help you."

So there are a number of interesting discussions and comments that are in this thread. The one thing in particular that really caught my attention is number 10, and it's "Advocate for junior developers." So they said that their friend reminded them that just because you don't have 10-plus years of experience does not mean that they won't be good. Without junior engineers on the team, no one will grow. Help others grow; you'll grow too.

And that's the part that I love so much is that without junior engineers on the team, no one will grow because that was very thought-provoking for me. It's something that I find that I agree with deeply, but I hadn't really considered why I agree with that so much. So I'm excited to dive into that topic with you. And then, as a second topic to go along with that is, can juniors start with a remote team? I think that's one of the other questions when you and I were chatting about this. And I'm intrigued to hear your thoughts.

CHRIS: A bunch of stuff there. Starting with the tweet, I love elements of this. Some of it feels like it's intentionally somewhat provocative. So like, without junior engineers on the team, no one will grow. That feels maybe a little bit past the bar because I think we can technically grow, and we can build things and whatnot. But I think what feels deeply true to me is truly help others grow; you'll grow too. The act of mentoring, of guiding, of training, of helping someone on their journey will inherently help you grow and, I think, change the way that you think about the work.

I think the beginner mind, the earlier in the career folks coming into a codebase, they will see things fundamentally differently in a really useful way. It's possible that along your career, you've just internalized things. You've been like, yeah, no, that was weird. But then I smashed my head against it for a while, and now I understand this thing. And it just makes sense to me. But it's like, that thing actually doesn't make sense. You have warped your mind to match the thing, not, quote, unquote, "come to understand it." This is sounding too judgmental to people who've been in the industry for a while, but I found this of myself.

Or I can just take for granted things that took a long time to adapt my head to, and if anything, maybe I should have pushed back a little more. And so, I find that junior engineers can be a really fantastic lens for the complexity of a project. Like, the world is truly a complex place, and that's just true. But our job as software engineers is to tame that complexity and manage it. And so, I love the mindset that can come or the conversations that can come out of that.

And it's much like test-driven development is a pressure on the complexity of your code, having junior engineers join the team and needing to explain how all of the different features work, and what the overall architecture is, and the message passing under this and that, it's a really useful conversation to have. And so that "Help others grow; you'll grow too" feels deeply, deeply true to me.

STEPH: Yeah, I couldn't agree more in regards to how juniors really help our team and especially, as you mentioned, with complexity and ¬having those conversations. Some of the other things that have come to mind for me as well around the importance of having junior developers on your team...and maybe it's not specifically they're junior developers but that you just have a variety of experience on your team. It's going to help you lean into a culture of learning because you have people that are at different stages of their career.

And so you want an environment where people can learn together, that they can fail together, and they can be public about it. And having people that are at different stages of their career will lead, well, at least ideally, it'll lead to more pair programming. It's going to lead to more productive code reviews because then people can ask more questions around why did you choose this, or why are you doing that? Versus if everybody is at the same level, then they may just intuitively have reasons that they think someone did something.

But it takes someone that's a bit new to say, "Hey, why did you choose this?" or to bring up some other ideas or ways that they could pursue it. They may bring in new ideas for, like, why has the team always done something this way? Let's think about new ways that we could do this. Or maybe this is really unfriendly, the way that we're doing this, not just for junior people but for people that are new to the team.

And then there's typically less knowledge siloing because then you're going to want to pair the newer folks with the more experienced folks. So that way, you don't have this more senior developer who's then off in a corner working by themselves. And it's going to improve your communication skills. There's just...I realized I'm just rambling because I feel like there are so many benefits that go along with having a variety of people on your team, especially in terms of experience. And that just leads to such a better learning environment and, ultimately, better software and better products.

And yet, I find that so many companies won't embrace people that are newer to software. They always want the senior developers. They want the 10x-er or whatever those are. They want the people that have many, many years of experience. And there's so much value that comes from mentoring the next group of developers. And it's incredibly frustrating to me that one, companies often aren't open to it. But honestly, more than that, as long as you're upfront and honest about like, hey, this is the team that we need right now to build what we're looking to build, I can get past that; I can understand that. But please don't then mislead people and say that you're a junior-friendly team, and then not be prepared.

I feel like some teams will go so far as to say, "Yes, we are junior-friendly," and they may even tweak their interview process to where it is a bit more junior-friendly. But then, by the time that person joins the team, they're really not prepared. They don't have an onboarding plan. They don't have a mentorship plan. And then they fail that person because that person has worked hard to get there. And they've worked hard to bring that person onto the team, but then they don't have a plan from there.

And I've seen it too many times. And it just frustrates me so much because it puts that junior person in such a vulnerable state where they really have to be an incredible self-advocate to then overcome those hurdles from a lack of preparation on that company's part. Okay, I think that's my event. I'm sure I could vent about this a lot more, but I will cut it off there. That's the heart of it.

CHRIS: I do think, like, with anything else, it's something that we have to be intentional about. And so what you're saying of like, yeah, we're a junior-friendly company, but then you're just hiring folks, trying to find folks that may work at a slightly lower pay grade, and that's what that means to you. So like, no, no, that's not what this is. This needs to be something different. We need to have a structure and an organization that can support folks at different points in their career.

But it's interesting to me to think about the sort of why of it. And the earlier part of this conversation, we talked about some of the benefits that can come organizationally from it, and I do sincerely believe in that. But I also believe that it is fundamentally one of the best ways to find really talented people early on in their career and be in a position to hire them where maybe later on in their career, that just wouldn't happen naturally. And I've seen this play out in a number of organizations.

I went to Northeastern University for my college, and Northeastern is famous for the co-op program. Northeastern sounds really fancy. Now I learned that they have like a 7% acceptance rate for college applications right now, which is wildly low. When I went to Northeastern, it was not so fancy. So just in case anyone's hearing that and they're like, "Oh, Northeastern, wow." I'm not that fancy. [laughs]

But they did have the co-op then, and they still have it now. And the co-op really is a differentiating thing. You do three six-month rotations. And it is this fundamental differentiator in terms of when you're graduating. Particularly, I was in mechanical engineering. I came out, and I actually knew what that meant in the world. And I'd used Outlook, and I knew what a water cooler was and how to talk near one because that's a critical thing to learn in the world. And really transformative experience for me.

But also, a thing that I observed was many of my friends ended up working at companies that they had co-opted for. I'm one of those people. I would say more than 50% of my friends ended up with a position at a company that they had done a co-op rotation with. And it really worked out fantastically. That organization and the individual got to try things out, experience. And then, I ended up staying at that company for a number of years, and it was a wonderful experience. But I don't know that I would have ended up there otherwise. That's not necessarily the way that would have played out.

And similarly like, thoughtbot has the apprenticeship. And I have seen so many wonderful developers start at that very early point in their career. And there was this wonderful structure around them joining the thoughtbot team, intentional, structured, supported. And then those folks went on to be some of the most talented developers that I've ever worked with at a wonderfully talented organization. And so the story of like, you should do this, organizations. This is a thing that you should invest in for yourself, not just for the individual, like, for both. Everybody wins in this case, in my mind.

I will say, though, in terms of transparency, I currently manage a team of three developers. And we hired very intentionally for senior folks this early on in where we're at. And that was an intentional choice because I do believe that if you're going to be hiring more junior developers, that needs to be something that you do very intentionally, that you have a support structure in place, that you're able to invest the time in where they're at and make sure we have sort of...

I think a larger team makes more sense to bring juniors into broadly. That's the thing that I'm saying out loud that I'm like, I should push on that a little bit. Is that true? Do I really believe that? But I think so, my actions obviously point to it. But it is an interesting trade-off space of how do you think about that? My hope is that as we grow as an organization, that we would then very intentionally start hiring folks in a more junior, mid-level to junior and be very intentional about how we support them, bring them into the organization, et cetera. I do believe it is a win-win situation for everyone when done with intention and with focus.

STEPH: That's such an interesting bit that you just said because I very much appreciate when companies recognize do we have the bandwidth to support someone that's more junior? Because at thoughtbot, we go through periods where we don't have our apprenticeship that's open because we recognize we're not in a place that we can support someone. And we don't want to bring someone in unless we can help them be successful. I very much admire that and appreciate that about companies when they can perform that self-assessment.

I am so intrigued. You'd mentioned being a smaller team. So you more intentionally hire senior developers. And I think that also makes sense because then you need to build up who's going to be in that mentorship pool? Because then people could leave, people could take vacations, and so then you need to have that support system in place. But yeah, I don't know what that then perfect balance is. It's like, okay, so then as soon as you have like five people available to mentor or interested in mentorship, it's like, then do you start bringing in the conversation of like, let's bring in someone that we can help build up and help them be successful and join our team? And I don't know what that magical number is.

I do think it's important for teams to reflect to say, "Can we take on someone that's junior?" All the benefits of having someone that's junior. And then just being very honest and then having a plan for once that junior person does arrive. What does their career path look like while they've joined that team, and who's going to be that person that's going to help them level up? So not only make that choice upfront of yes, we are bringing someone on but let's also think about like the first six months of their work here at the company and what that's going to look like.

It feels like an important step that a lot of companies fail to do. And I think that's why there are so many articles that then are like, hey, if you're a junior dev, here's all the things that you should do to be the best junior dev. That's fabulous. And we're constantly shoring up junior devs to be like, hey, here's all the things that you need to be great at. But we don't have as many conversations around; hey, here's all the things that your manager or the rest of your team should be great at to then support you equally as you are also doing your best to meet them. Like, they need to meet you halfway.

And I'm not completely unsympathetic to the plight; I understand. It's often where I've seen with teams the more senior developers that have very strong mentorship communication skills are then also the teammates that get pulled into all the meetings and all the different projects, so then they are less available to be that mentor. And then that's how this often fails. So I don't think anybody is going into this intentionally, but yet, it's what happens for when someone is new and joining a team, and it hasn't been determined the next six months what that person's onboarding and career path looks like.

Circling back just a bit, there's the question around, can juniors start with a remote team? I can go first. And I'm going to say unequivocally yes. There's no reason a junior can't start with a remote team. Because all the things that I feel strongly about come down to how is your team going to plan for this person? And how are they going to support this person? And all the benefits that you get from being in an office with a team, I think those do exist.

And frankly, for someone like myself, it can be easier to establish a bond with someone that you get to see each day, get to see in person. You can walk up to their desk and can say, "Hey, I've got a question for you." But I think all those benefits just need to be transferred into a remote-friendly way. So I think it does ratchet up how intentional you have to be with your team and then onboarding a junior developer. But I absolutely think it's doable, and we should do it.

CHRIS: You went with unequivocally yes as your answer. I'm going to go with a qualified maybe as my answer. I want this to be true, and I think it can be true. But I think it takes all the more intentionality than even what we've been describing. To shift the question around a little bit, what does remote work mean? It doesn't just mean we're doing the work, but we're separate. I think remote work inherently is at its best when we also are largely async first. And so that means more structured writing.

The nature of the conversation tends to be more well-formed in each interaction. So it's like I read a big document, and then I pass it over to you. And at your leisure, you respond to it with a bunch of notes, and then it comes back to me. And I think that mode of interaction, while absolutely wonderful and something that I love, I think it fits really well when you're a little bit further on in your career when you understand things a little bit better. And I think the dance of conversation is more useful earlier on and so forth.

And so, for someone who's newer to a team, I think having the ability to ask a quick question over and over is really useful to someone who's early on in their career. And remote, again, I think it's at its best when it's async. And those two are sort of at odds. And so it's that mild tension that gives me pause of like, something that I think that makes remote work great I do think is at least a hurdle that you would have to get over in supporting someone who's a little bit newer. Because I want to be deeply present for someone who's newer to their journey so that they can ask a lot of questions so that I am available to be interrupted regularly.

I loved at thoughtbot sitting next to someone and being their mentor and being like, yeah, anytime you want, just tap on my desk. If I got my headphones on, that doesn't mean I'm ignoring you; it means I just need to make the sounds go away for a minute because that's the only way my brain will work. But feel free to just tap on my desk or whatever and grab my attention for a moment. And I'm available for that. That's an intentional choice. That's breaking up my continuity of the day, but we're choosing that for a reason.

I think that's just a little harder to do in a remote context and all the more so if we're saying, hey, we're going to try this async thing where we write structured documents, and we communicate in these larger, more well-formed, communicates back and forth. But I do believe it can be done. I think it should be done. I just think it's all the harder for all of those reasons.

STEPH: I agree that definitely makes it harder. But I'm going to push a little bit and say that when you mentioned being deeply present, I think we can be deeply present with someone and be remote. We can reduce the async requirements. So if you are someone that is more senior or more accustomed to the team, you can fall back to more of those async ways to communicate.

But if someone is new, and needs more mentorship, then let's just set up time where we're going to literally hang out for a couple of hours each day or whatever pairing environment works best for them because pairing can also be exhausting. But hey, we're going to have a check-in each day; maybe we close out each day and touchpoint. And feel free to still message me and interrupt me. Like, you're going to just heighten your availability, even though it is remote. And be aware, like, hey, this person could message me at more times, and I'm okay with that. I have opted into this form of communication.

So I think we just take that mindset of, hey, there's this person next to me, and I'm their mentor to like, hey, they're not next to me, but I'm still their mentor, and I'm still here for them. So I agree that it's harder. I think it falls on us and the team and the mentors to change ourselves versus saying to juniors, "Hey, sorry, it's remote. That's not going to work for you." It totally works for them. It's us, the mentors, that need to figure out how to make it work.

I will say being on that mentor side that then not being able to see someone so if they are next to me, I can pick up on body language and facial expressions, and I can tell when somebody's stuck. And I can see that they're frustrated, or I can see that now's a good time for me to just be like, "Hey, how's it going? What are you working on? Or do you need help with something?" And I don't have that insight when I'm away. So there are real challenges like that that I don't know how to address.

I have gone the obnoxious route [laughs] where I just message people, and I'm like, "Hey, how's it going? How's it going? How's it going?" And I try not to do that too much. But I haven't found a better way to manage that other than to constantly check in because I do have less feedback from that person that I'm working with unless they are just incredibly open about sharing when they're stuck. But typically, when you're newer to a team or newer to a career, you're going to be less willing to share when you're stuck.

But yeah, there are some real challenges, but I still think it's something for us to figure out. Because otherwise, if we cut off access for remote teams to junior folks, I mean, that's where we're headed. There are so many companies and jobs that are headed remote that not being junior friendly and being remote in my mind is just not an option. It's something that we need to figure out. And it's hard, but we need to figure it out.

CHRIS: Yeah, 100% on we need to figure that out and that that's on us as the people managing and structuring and bringing folks into teams. I think my stance would be like, let's just be clear that this is hard. It takes effort to make sure that we've provided a structure in which someone newer to a team can be successful. It takes all the more effort to do so in a remote context, I think. And it's that recognition that I think is critical.

Because if we go into this with the wrong mindset, it's like, oh yeah, it's great. We got this new person on the team. And yeah, they should be ready to go in like two weeks, right? It's like, no, no, this is a different thing. We need to be very clear about it. This is going to require that we have someone who is able to work with them and support them in this. And that means that that person's output will likely be a little bit reduced for the period of time that we're talking about. But we're playing a long game here. Let's make sure we're clear on that. This is intentional.

And let's be clear, the world of hiring and software right now it's not like super easy. There aren't way more software developers than there are jobs; at least, that's been my experience. So this is something absolutely worth investing in for just core business reasons and also good for people. So hey, it's a win-win. Let's do it. Let's figure it out. But also, let's be clear that it's going to be a little tricky along the way. So, you know, let's be intentional about that. But yeah, obviously do it, got to do it.

STEPH: Wait, so I feel like we might have circled back to unequivocally yes. [laughs] Have we gotten there, or are you still on the fence?

CHRIS: I was unequivocally yes from the beginning, but I couched it in, but...yeah, I said other things. You're right. I have now come around; let's say to unequivocally yes.

STEPH: [laughs] Cool. I don't want to feel like I'm forcing you to agree with me. [laughs] But I mean, we just so rarely disagree. So we've either got to identify this as something that we disagree on, which would be one of those rare occasions like beer and Pop-Tarts.

CHRIS: A watershed moment. Beer and Pop-Tarts.

STEPH: Yeah, those are the only two so far.


CHRIS: Not together also. I just want to go on record beer and Pop-Tarts; I don't think would be...anyway.

STEPH: Ooh, I don't know. It could work. It could work.

CHRIS: Well, there's another thing we disagree on.

STEPH: I would not turn it down. If I was eating a Pop-Tart, and you're like, "Hey, you want a beer?" I'd be like, "Sure," vice versa. I'm drinking a beer. "Hey, you want a Pop-Tart?" "Totally."

CHRIS: Okay. Well yeah, if I'm making bad decisions, I'm obviously going to chain them together, but that doesn't mean that they're a good decision. It's just a chain of bad decisions.

STEPH: I feel like one true thing I know about you is that when you make a decision, you're going to lean into it. So like, this is why you are all about if you're going to have a Pop-Tart, you're going to have the highest sugary junk content Pop-Tart possible. So it makes sense to me.

CHRIS: It's the Mountain Dew theorem, yeah.

STEPH: I didn't know this had a theorem. The Mountain Dew theorem?

CHRIS: No, that's just my name. Well, yeah, if I'm going to drink soda, I'm going to drink Mountain Dew, the nonsense nuclear option of soda. So yeah, I guess you're describing me, although as you say it back to me, I suddenly feel very, like, oh God, is this who I am as a person? [laughs] And I'm not going to say you're wrong. I'm just going to spend a little while thinking about some stuff.

STEPH: I mean, you embrace it. I think that's lovely. You know what you want. It's like, all right, let's do this. Let's go all in.

CHRIS: Thank you for finding a wonderfully positive way to frame it here at the end. But I think on that note, should we wrap up?

STEPH: 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.

CHRIS: If you enjoyed listening, one really easy way to support the show is to leave us a quick rating or even a review on iTunes, as it really helps other folks find the show.

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 hosts@bikeshed.fm via email.

CHRIS: Thanks so much for listening to The Bike Shed, and we'll see you next week.

ALL: Byeeeeeeee!!!!!!!!

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