340: Solving People Problems with Rob Whittaker

Episode 340 · May 31st, 2022 · 50 mins 36 secs

About this Episode

Steph is joined by a very special guest and fellow thoughtbotter, Rob Whittaker.

Rob shares how he became the Software Development Director for Launchpad II, thoughtbot's Europe, Middle East, and Africa team. They also dive into what it's like to be a Development Director, the differences between mentoring and coaching, working with GitHub Codespaces, and strategies for boosting your creativity and problem solving capabilities.

thoughtbot is hiring!
Time Off Book
Rob's Codespace Setup
Rob Whittaker on Twitter

Become a Sponsor of The Bike Shed!


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. And today, I'm joined by a very special guest and fellow thoughtboter, Rob Whittaker.

Rob has been in the software business for the past 15 years and spent the last five and a half years at thoughtbot. Rob is the Director of Software Development for our Europe, Middle East, and Africa team and, in his spare time, likes to hunt down delicious beers and coffee. Rob, welcome to The Bike Shed. It's so lovely to have you on the show today.

ROB: Thank you for having me. It's a pleasure to be here. Yeah, thank you for that lovely introduction and my far too complicated job title. It sounds more serious than it actually is.

STEPH: Well, you do have a fancy job title, yeah, Director of Software Development. [laughs]

ROB: Yeah, it's the added on bit where it's Europe, Middle East, and Africa where I feel like there's about 20 of us maximum. But that sounds more grandiose than it actually is.

STEPH: Yeah, that's something that Chris and I haven't dug into too much on previous episodes are all the different teams that we have at thoughtbot. So the shorter way of saying that is Launchpad II, but not everybody knows that. But I'm going to circle back to that because I would love to talk a bit more about that specific team and the dynamic. But before we do that, I'm realizing I'm not familiar with your origin story as to how you came to thoughtbot and then how you became this very fancy grand title of Director of Software Development for Europe, Middle East, and Africa team.

ROB: Yeah, there's a bit of history about thoughtbot London as well that kind of ties into this. So before thoughtbot Launchpad II, it was thoughtbot London before we went remote. And initially, we had the plan of setting up a new studio in London to help expand thoughtbot outside of the Americas, but that plan fell through. But he knew some people from another agency called New Bamboo, and so we merged with or acquired that agency, and that agency then became the thoughtbot London team. I'm actually the first hire or...not the first hire, that's not true, the first development hire for the thoughtbot London team that would then become launchpad II.

I was at the Bath Ruby Conference six years ago, I guess. And there was just an advert up on the hiring board that Nick Charlton, who's a Senior Developer and Development Team Lead at Launchpad II now, had put up. And I saw it, and I was talking to somebody who was my mentor at the time that I'd worked with at a previous job at onthebeach.co.uk, a guy called Matt Valentine-House who now works at Shopify who, actually, fun fact, his face appears at the top of Ruby Weekly this week. If you open up this week's Ruby Weekly, you can see Matt Valentine-House, who said to me, "Yeah, apply for it, why not? You see what happens." And I was like, "Okay," and just kind of took the leap.

So I thought, thoughtbot, why would thoughtbot want me? Which is something I think a lot of people think when they want to join thoughtbot. They think, well, I can't do that. But I would implore people to apply. And so, from there, I never really wanted to move to London. I'd always lived in the North West of the UK. I made that leap to London because I wanted to work at thoughtbot. And then, gradually, over time, the London team expanded, and we needed to split out the management roles, and the development director role came up.

And I've always enjoyed the coaching side of software development. It seems that you gain more experience as you help people with less experience, and I've always enjoyed coaching. And that was a big part of the role for me. So I was fortunate enough to be allowed to do it. And then, from there, things have grown. Yeah, so it's been a really interesting journey as a development director.

The London studio went through a pretty tough time at one point where not long after I became development director that two-thirds of the team, in the space of two weeks, decided to hand their notice in and unbeknownst to each other. And so, all of a sudden, we didn't have a very big team. We didn't have very many prospects, and so it was a tough time. And so it's really nice to look back on the last three years and go, okay, we came through that. We're now one of the stronger teams at thoughtbot.

And somebody actually asked me in an interview the other day, somebody we actually hired, not just based on this question, but he said, "What is your proudest moment of working at thoughtbot?" And I was like, that's one of the best questions I've heard from a candidate. And I said, "Hmm, that's interesting." It's not anything development-related, but it's that I can now look back on this team and say this is the team that I have grown in my image and all these people apart from Nick, who was the person who put the advert of it at Bath Ruby.

I've hired all these people, and so the buck stops with me really because if anybody isn't able to perform, then it's kind of my fault because these are the people that I want to grow into being the team and see be a successful product design team or product development team, which brings us to modern-day I guess. So yeah, that was a long origin story. That's pretty much my whole thoughtbot biography. And I apologize.

STEPH: That was perfect. I thoroughly enjoyed hearing it. And yeah, that's an awesome question. What's your proudest moment, like, part of a team? That can yield so many insights. I love that question. And I love your answer as well in terms of this is the team. We've pulled through a hard time. And then we've built everybody to the point that they are now, which kind of leads in perfectly to my next question.

So being the software development director, could you walk us through a little bit of like, that's one of those titles I feel like a lot of companies have, but they can be very different from company to company. Would you mind walking us through a bit of the day-to-day in the life of being a development director?

ROB: Yeah, sure. It's one of those things where I think this is something that I'm not sure if it's unique to thoughtbot, but you end up taking on a lot of hats at thoughtbot. So I know you're a team lead. So you have to balance your responsibilities as an individual contributor, which is a term I don't like, but I haven't got a better way to say it yet, and your development team lead roles. And I have similar sort of responsibilities where I have to do my individual contributor work. I have to do my director work. I'm also on our DEI Council. So I have to add that work in too, and make sure it's balanced out.

So the start of my day is very much about prioritizing things. I know you and Chris, a few episodes ago, had quite lengthy discussions about productivity systems and what tools Chris wants to use. And I'm a big fan of Things, and I've been using it for maybe ten years, if not more, that I've now got my system down that I'm able to prioritize things in the way that I can pick up the right task at the right time. So a big part of my day-to-day is figuring out what is the most important thing to work on? So I have my client work, and then it's about supporting the team from that point.

And the big part of my idea of what a manager is is that my job isn't to tell you what to do; my job is to find out what you want to do and direct you in a place where you can find the answer. Or I can give you some guidance about where to find the answer. And I feel like I'm doing a bad job as a manager where if I have to act as a middle person. Because if somebody comes to me and says, "Oh, I want to do this thing," And I say, "Well, I'll talk to that person for you," and then come back, I have failed.

And my job is to say, "Oh, you should talk to that person about this." And to some extent, it's about being lazy. I don't want to be doing too much stuff because I have other things to do. But I want to make sure that those people have the right frameworks and guidelines in place so that I can point them in the right direction.

STEPH: I think the fancy term for that is just delegating. [laughs]

ROB: Yes, thank you. [laughs]

STEPH: But I like lazy. [laughter] I like that one as well. I love that framing of a manager where you're not telling someone to do, but as your job, you are helping that person figure out what they want to do and then supporting them. I've been chatting with Chris recently and some others because I've been reading the book Resilient Management by Laura Hogan. And it's really helped me cement the difference between mentorship, coaching, and sponsorship.

And I realized that I'm already falling a lot into the coaching and sponsorship because mentorship can be wonderful, but it is more directive of like, this is what I've done. And this is what has worked for me, and you should do this too. Versus the coaching and sponsorship, I think aligns far more perfectly with what you described as management, where it is my job to figure out what brings you joy, what brings you energy, and then how to help you progress to your next goals and your next steps in your career.
ROB: Yeah, I think Laura Hogan is a great resource like her blog posts and books. I haven't read Resilient Management. But I know that the team leads on my team had been on her training courses, and they say how great it is. And there's also a blog post of hers that's about managing in tough times. It has a much better title than that. But it's about how do we be good managers in such uncertain times when there are a lot of things going on around the world right now that we all have to deal with? And helping people deal with those situations.

Because at the end of the day, work isn't the most important thing; the most important thing is living. And it's something I say to my team, especially when people feel like...it's something that I say to my team when they're not feeling well. The most important thing is that you get better. And thoughtbot is still going to be here. The most important thing is how you live your life and how you look after yourself, and everything else is secondary.

STEPH: Absolutely. Well, and everybody needs something different from work too. Some people may be in a state where they really need more stability and predictability from their work. And some people may be in a space where everything else outside of work is very stable and calm, and then they want work to bring the challenge and the volatility and the variety to life.

So I remind myself very often that not everybody wants the same thing from work and to figure out what it is that someone wants from work. And then your seasons change. You may be in a season of where you want stability, or then you may be in a season of like, I'm ready to grow and push and take some risks. So helping someone identify which season of work they're in.

ROB: Yeah, I 100% agree. What people can't see is me nodding vigorously on the other side of this call. It's very much about understanding because everybody is different. And that's what we want from a good team; it's understanding everybody's different approach to things. And so sometimes people want the distraction of work because they don't want the time off to think about other things. They want to be able to sit and concentrate on something. And it's understanding different people.

STEPH: Yeah, that's a great point. I'm curious; you mentioned that as part of being development director, you are also, in addition to managing the team and being part of DEI then, there's also your day-to-day client work. I think you've started a new client recently. Could you tell me more about that?

ROB: Yeah, I'd recently been working for a client for two and a half years, which is a very long time to be working with one client at thoughtbot. And it came to the time where I was ready for a new challenge, and it was stable enough for me to move on. So I've been working for a company in the UK. They allow customers to buy and sell cars, not between customers, the customers like companies like Auto Trader but customers to dealers and back and forth. And primarily, they worked with buying cars. And they've launched a product in the UK where people can sell their cars as well because they found that 70% of people who are buying cars also want to sell their cars.

And from there, they're now looking to expand into Germany and Spain, so we are helping them to do that. And it's an interesting project, not necessarily from a technical point of view, but I might come back to that but definitely from a cultural point of view. The product at the moment allows you to put in a license plate or a registration plate for a car. And there's then a service in the UK that will allow you to pull up the maker model and the service history of that car. But you can't do that in Germany because it's against the privacy laws to find something from registration plates.

And so it's interesting these different cultural aspects that you have to take into account when expanding into other countries that you aren't from and that you have less knowledge about. Because I'm also aware that credit cards aren't a big thing in Germany either. So you have to think about how they pay for things in different countries. And the previous company I was working for they're based in the Middle East. And so we had to take into account how we would do right to left design in a mobile app, which is really interesting from a western point of view that you get so used to swiping through an experience from left to right.

But then it's not just the screen that's right to left. The journey moves from right to left. So you have to get used to the transitions of the screen going the other way and not thinking of that as going backwards. It's one of the best things about working in this region is that we get to deal with so many different cultures and how they expect to use applications. It's really satisfying.

STEPH: That's fascinating. Yeah, I haven't gotten to work on a project like that that has those types of considerations. I think the most relatable experience I have is more working in healthcare because that's one of those areas that I'm certainly not proficient. I've become more proficient because of the type of projects that I've worked on.

But I'm curious, for expanding into other regions and cultures, do those teams typically have an expert on their team that then helps guide the development process? Or, as you mentioned, the process of buying a car could be very different in some of the legal aspects that you're up against. Is there someone that you can turn to that's then helping mentor or be aware of that process?

ROB: Yes, the current client they have a team based in Germany, people who are from Germany that are advising us on different cultural aspects or legislative things. They are doing a lot of data analysis for us because we need a new service that we can use for looking up car details. Because there is a service that you give different information to to get information about the car back from. So yeah, we do have that team there. But that's not always the case because every client is different.

The company that we're working for in the Middle East didn't have a team. They had two developers who were helping us. But we have to figure things out just from their cultural background to ask them questions about things and allow them to advise us, but nobody who was really a specialist. But that's an interesting thing as well, not just the cultural aspects of the customers but the cultural aspects of the company that you work for.

We definitely found that the company in the Middle East was more hierarchical. And so that's another challenge that you have to work with because we tend to work in quite a flat way where we tend to default as on thoughtbot projects, of not having a point person on a project. Everybody is there to answer the questions. But some teams or clients want that point person. And so, we adapt and change to allow for that to happen and work in that way. But it is interesting to work in different companies as well as working as an agency.

STEPH: Yeah, you bring up a really good point of something that I don't reflect on very often, but it's something that I really appreciate about our thoughtbot culture is that we do try to strive for a very flat hierarchy. But also in working with clients, we purposely will avoid like, if there are two or more thoughtboters on a project, we don't want one person that is then the primary contact between the client and the thoughtbot team. The goal is that everybody shows up. Everybody is part of the process; everybody is part of meetings.

And we do have an advisor for projects, but otherwise, we work very hard to make sure that there's not just one person that's then responsible for communication. We want everybody to have opportunities to be part of meetings, to lead meetings, to take on initiatives versus having that one person. That is something that I really appreciate that we do.

ROB: Yeah. And it's more noticeable when you go to places where that isn't the norm, and you appreciate it more. And I think a big part of that is how much we are trusted. And we trust people to trust us, I guess.

STEPH: Yeah. And I think it fits in nicely with circling back to the management conversation is that when people have access to those opportunities, that makes my job so much easier as a team lead where then there are more opportunities to sponsor someone or to coach someone as to how they can then be the person that then takes on a project or if they want to lead a particular meeting, or if they want to help a team introduce retrospectives into their process. So it gives more opportunities for me to then coach someone into expanding their skill set in those ways.

ROB: Yeah, that's interesting to think about, allowing yourself to coach other people in that role. Because as we gain more experience and become senior developers, we naturally fall into that role of taking the lead on projects, even when we're not asked to. But then, when you gain other responsibilities in the management track, so you as a team lead and me as a team lead and a development director, it could be better for you to not take that role and allow somebody else to come into that role so you can coach them. That's been playing on my mind the last couple of days.

Josh Clayton, who's the Managing Director for one of our teams in the Americas, raised it on our pull request in our handbook where we were talking about team leads having a dedicated day to concentrate on team lead things. It's one of those things where somebody says something, and it's like, oh yeah, that really clicks. Maybe that's why we have been having certain struggles on projects where we need to rearrange things and learn from that and so we can be better on projects in the future. So that's something that really resonated with me, and it's flying around in the back of my mind at the moment.

STEPH: Yeah, that really resonates with me because while the predominant part of being a team lead at thoughtbot is having one-on-ones with folks, I find that when I have more time, a lot of the work also falls outside of that one-on-one where it's following up on conversations around hey, this person mentioned they're really interested in growing their skill. How can I help them? How can I help find opportunities?

Or I know that they're currently stretching their skill set right now. If I have some extra time, then I can check in with them. I can pair with them. I can see how things are going. So I find that while the one-on-ones are the staple thing that happens every two weeks, there's a lot of other behind-the-scenes work that's going on as well to make sure that that person is growing and feeling really fulfilled by their work.

ROB: I know we've spoken a lot about the product side and the client side of working on the new project that I'm working on. There are some interesting technical sides to it as well. The client has found that they have had some issues with Haskell and running on M1 Macs. And so, they've decided to take the leap and use GitHub Codespaces as their primary development environment, which has been interesting. I had heard about it but only in the background. I hadn't read anything about it or hadn't had any direct conversations. I just heard that there was a thing. So it's been quite interesting to play with that.

It's interesting the way the client is using it as well because they're using a Dockerized environment effectively inside Docker by using Codespaces. So you start the Codespace, which very basically is a Docker instance somewhere on GitHub's infrastructure. It's built very much for Visual Studio Code, and so you can just directly attach your Visual Studio Code session to the Codespace and go from there, but I'm a Vim user. I've started to feel like a bit of an old guard or a curmudgeon recently where I've been like; maybe I need to use Visual Studio Code. Maybe I should just unlearn my Vim key bindings and learn the Visual Studio ones.

And people say, "Oh, you could just use The Vim key bindings in VS Code." I'm like, that's cheating. I spent the time to learn the key bindings for Vim. I will take the time to learn the key bindings for Visual Studio Code and use it for the way it's intended. So it's been interesting to understand how Codespaces works, not necessarily in the way, it's intended. So you can still SSH into a Codespace session, but then you lose all the lovely setup stuff that you might have on your local machine.

So I did spend half a day porting my dotfiles which are based off thoughtbot's dotfiles, into something that Codespaces can use and made it publicly available. So if you go to github.com/purinkle/codespace, you can see what I use to set up my Codespace environment. And once that's set up, it becomes a bit easier because then you have all the things that you're used to running locally. It is very much early days for how the client is using it. And so they're really open to saying like, okay, let's find out what's not working, and let's work and figure out how to get it up and running properly.

So one of the things we do find is that Codespaces do timeout after a while. And then you might lose, like, even if I've created a tmux session, that tmux session disappears. And so I have to go in and create it again. I'm not sure what the timeouts are. I haven't had time to look into what those timeouts are yet. But that's definitely the main pain point at the moment of it being used as a development environment.

It's been interesting. It's been kicking around in the back of my head like the difference between developing locally and deploying locally. And it's something that I wanted to talk to people at thoughtbot and outside of thoughtbot as well to understand that more. Because I don't think you need everything running to develop locally, but you might need it to deploy locally. It's interesting to me to understand how different companies work on their products from that point of view.

STEPH: Yeah, I'm selfishly excited that you are using Codespaces for a client project because I have kept an eye on it, and I'm very intrigued by it. But I also haven't used it for a project. And it sounds really neat. I'm curious, have you found that it has helped them with onboarding or if you need to switch from working on one application to another? Have you found that it has helped them with some of those? I'm guessing that's the problem that they're optimizing to solve is how do we help people run everything quickly without having to set it up locally?

ROB: It's an interesting question because I don't have the comparison of trying to set up the environment as it was before. It was smoother. The main thing with access tokens because once you can set up your SSH keys and your GitHub tokens, it's just a case of running a script and letting it run. So yes, from that point of view, I can imagine if I tried to set up their previous environment, that it'd be a lot more challenging because they were using Vagrant and running things that way, which I know from experience would not be fun.

And I know that my Mac fans would just be spinning all the time. It would be like an aeroplane was trying to take off. So I'm thankful for that, that I don't have that experience anymore that my machine is going to slow down all the time. We've had on a previous client who had a Dockerized environment, but you have to have it all running on your machine. There are pros and cons to everything with these things. And it's like you said, what is the problem they're trying to solve with introducing this setup?

STEPH: Yeah, I can't decide if this is a good thing or a bad thing. But I'm also intrigued by the idea that if a team is using Codespaces, then that means everybody else is using VS Code. And you can still customize it so you can still have your own preferences. But that does set a standard, so everybody is using the same editor. There's a lot of cross-collaboration in terms of if you do run into an issue, then you can help each other out.

Versus when I join other teams, everybody's using their preferred editor, and then there you may have a day where someone's like, "Oh, I'm really stuck because my particular editor is suddenly having a problem and can't connect." And then you have less people that are able to help them if they're not using that same editor. And I can't decide if I like that or if I hate it [laughs] in terms of taking away people's ability to pick and choose their editor. But then the gains of everybody is using the same thing which is nice and would be really great for pairing too.

ROB: Yeah, that's an interesting point. I was talking to...I have a management coach. He's a PHP developer, and I'm a Rails developer. And we were talking about the homogenization of things nowadays. And is that good, or is that bad to use with stuff like RuboCop that lints everything, so it's exactly the same? Does that stifle creativity? But then, at the same time, the thing I like about Codespaces is I think we're biased coming at it from the point of view of Rails developers.

And if you look at how you can use Codespaces in the browser directly from GitHub, that's quite interesting because now you're lowering the barrier to entry to get started and saying you don't need to have an editor. You don't have to set up everything. You can just do it from your browser. A few years ago, I used to volunteer or coach at an organization called codebar. They help people who are less represented in the tech community get represented in the tech community. And we would see a lot of people coming for sessions using...I forgot what it's called. What was it called? Cloud 66 or something.

There was some remote development environment that people would come and say, "Oh, I've been using this," because they didn't know how to set up the necessary infrastructure to just get a Rails server going or things like that or didn't know how to set up Sublime or Atom or editor of choice. And it's really interesting if you remove your bias of 15 years of professional software development and go okay, if I were starting today, what would the environment look like, and how would I get started?

I'm lucky enough that I've grown up with the web and seen how web development has changed and been able to gain more knowledge as it's appeared. I don't envy anybody who has to come into the industry now and suddenly have to drink from this firehose of all these different frameworks, all these different technologies. Yeah, I started off by just right-clicking and viewing source on HTML files back in 1998 or something ridiculous like that. And CSS didn't even exist or wasn't used. And so it's a much different world than 24 years ago.

STEPH: That is something that Chris and I have mentioned on previous episodes where people are coming into software development, and as much as we love Vim and it sounds like you love Vim, our advice is don't start with Vim. Don't start there. You've got so much to learn. Start with something like VS Code that's going to help you out.

And you make such a great point in regards to this lowering the barrier to entry. Because I have been part of a number of classes where you have people coming in with Macs or with a Windows machine, and then you're trying to get everybody set up. You want them to use the same browser for testing. And we spend like a whole class just getting everybody on the same page and making sure their machines are working or then troubleshooting if something's not.

But if they can just go to GitHub and then they can run things seamlessly there, that's a total game-changer in terms of how I would teach a class, and it would just be far easier. So I hadn't even considered the benefits that would have for teachers or just for onboarding teams as well. But yeah, specifically for leading a class, I think that is a huge benefit.

GitHub did some pretty cool stuff around when they were launching that as well because I went back and watched some of their GitHub Universe sessions that they had where they were talking about Codespaces. And one of the things that they did that I really appreciated was how they went about launching Codespaces. So initially, it was how fast can this be? Or what's our proof of concept? And I think when they were building this, they found it took about 45 minutes if they wanted to spin up an application and then provide you a development environment. And they're like, okay, cool, like, we can do this, but it's 45 minutes, and that's not going to work.

And so then their next iteration, they got it down to 25 minutes, and then they got it down to 5 minutes. And now they've got it to the point that it's instantaneous because they're building stuff in the background overnight. And so then that way, when you click on it, it's just all ready for you. But I loved that cycle, that process that they went through of can we even do this? And then let's see, slowly, incrementally, how fast can we get it?

And then, to get feedback, instead of transitioning their own internal teams to it right away, they created this more public club. I think they called it The Computer Club, something like that. And they're like, hey, if you want to be part of Codespaces or try out this new feature that we have, delete all the source and the things that you need locally, and then just commit to using Codespaces. And then, if you are stuck or if you have trouble, then your job is to let us know so then we can iterate, and we can fix it. I really liked that approach that they took to launching this product and then getting feedback from everyone and then improving upon it.

ROB: Yeah, that sounds like an Agile developer's dream where you just put something out there that's the bare bones, and you're given license to learn from that experience and how people are actually using that tool. That's something we've actually tried to do on the client project at the moment is adding all the...now that there's a different flow in Germany, there are different questions we need to ask. And so that could be quite a complex thing to put into place.

So what we said is what we're going to do is just put in the different screens, and all you have is one option to click. So you click that option, you go to the next one, go to the next one, go to the next one. Then we have something that the customer can click on and play with and understand, and then we can iterate on top of that. But it also allows us to identify areas of risk because you can go; oh, where does this information come from? But now we need to get this from a third-party service.

So that's the riskiest thing we've got to work on here, where this other thing is just a hard-coded list of three-door or five-door cars. And so that's an easier problem to solve. So allowing yourself to put something that could be quite complex like GitHub Codespaces and go okay, we're going to put something out there. It takes 45 minutes to run-up. But we're telling you it takes 45 minutes to run it. We're not happy with it, but we want to learn how you're using it so that we can then improve it but improve it in the right direction.

Because it might be that we get it to 20 minutes to start up, but you need it in half a second. That's a ridiculous example. Or it might be that you need to be able to use RubyMine with it instead of VS Code, and that's where the market isn't. That's the thing that you can't learn in isolation that you have to put something out there for people to use and play with.

STEPH: There's one other cool feature I want to highlight that I realized that they offer as well. So in the past, I've used a tool called ngrok, which then you can make your localhost public so other people can access. You can literally demo what you're working on locally, and someone else can access it. And I think that it's very cool. It's come in handy a number of times. And my understanding is that Codespaces has that feature where they can make your localhost accessible. So your work in progress you can then share with someone, and I love that.

ROB: Oh, that's really interesting. I didn't know you could do that. I know you could forward ports from your local machine to that. But I didn't know you could share it externally. That'd be really cool. I can see how that can be really helpful in demos and pairing. And it makes sense because it's not running on your computer. It's running on some remote architecture somewhere. That's interesting.

STEPH: Well, that's the dream I've been sold from what I've been reading about GitHub Codespaces. So if I'm telling lies, you let me know [laughs] as you're working further in it than I am. But yeah, that was one of the features that I read, and I was like, yeah, that's great because I love ngrok for that purpose. And it would be really cool if that's already built into Codespaces as well.

ROB: ngrok is really interesting with things like trying to get third-party services to work. So from, the previous client, they wanted an Alexa Skill. And so, if you're trying to work with an Alexa Skill, you have to sign in from Amazon's architecture onto your local machine. You have to use ngrok as the tool there. So I wonder if that could potentially solve a problem where if there are three developers trying to develop on this if you could point to one Codespace that you're all working on rather than...

Because the problem we had was if me or Fritz or Rakesh was working on this, we'd have to go and then change the settings on the Amazon Alexa Skill to point to a different machine. Whereas I wonder if Codespasces allows you to have this entry point, you could point to like thoughtbot.codespace.github.com or something like that that would then allow you to share that instance. That's something interesting that I think about now. I wonder if you could share Codespace instances amongst each other. I don't know.

STEPH: Yeah, I'm intrigued too. That sounds like it'd be really helpful. So circling back just a bit to where we were talking about wearing different hats in terms of working on client work, and then also working on the team, and then also potentially some sales work as well, I'm curious, how do you balance that transition? How do you balance solving hard problems in a codebase and then also transition to solving hard problems in the management space? How do you make all of that fit cohesively in your day or your week?

ROB: The main thing that somebody said to me recently is that you can only do so much in a day, and it's about the order that you approach those things. And just be content with the fact that you're not going to get everything done. But you have to make sure that you work on things in the right order and just take your time and then work through them. I read a really good book recently that was recommended to me by my coach called Time Off. And it's all about finding your rest ethic, which sounds a bit abstract and a bit weird. But all it is it's about understanding that you can't be working 100% all the time. It's not possible.

As developers, sometimes we can forget that we're creative people, and creativity comes from a part of your brain that works subconsciously. So it's important for you to take breaks throughout the day and kind of go okay; I use the Pomodoro Technique. So I have an app that runs, and every 25 minutes, I just take a little break. I don't use it in the way that it's supposed to be used. I just use it to give me a trigger to have a break every 25 minutes. And so in that time, I'll just step away from my computer. I'll walk to the kitchen, grab a glass of water.

I usually have a magazine or a book next to my table. So I have a magazine here at the moment. I'll just read a page of that just to kind of rest my eyes, so they focus at a different level but also just to get my brain thinking about something else. And it seems counterproductive that like, oh, you're stepping out of what you were doing. But then I find like, oh, I suddenly have a little refresher to like, oh, I need to get back into what I was doing. I know where I've got to go. That thing that I was thinking about now makes a little bit more sense. And even if it's a bigger break, give yourself the license to go for a walk and just kind of clear your head.

And a big thing about going for a walk is not to concentrate on completing the task of walking but to concentrate on the walk itself and taking the things that are happening around you. And let your mind just kind of...you'll sometimes notice that oh, I can hear a bird. But that bird's been chirping for five minutes, and you didn't notice because your mind's kind of going. And if you concentrate on, I just want to complete this walk, that's what I'm out here to do, then you lose that ability to let your mind reset. That's a big thing that I'm working on personally to concentrate on the doing rather than the getting done.

And it ties into the craft of being a software developer because if you concentrate on the actual writing of the code and the best practices that we all believe in, you end up with something better that you don't then have to revisit at a later time. Where if you just try and get something done, you're just going to end up having to come back to it or have to revisit in some other way. I've actually got a blog post coming out soon about notifications on phones. I'm a big believer that your phone belongs to you and that if your work wants you to have work notifications on your phone, then they could buy you a phone just for that purpose.

The only thing where I kind of draw the line is I have notifications for meetings on my phone because I can't think of another way to get those things to ping up at me. And I understand that there are jobs where you do need to have those sorts of notifications, especially things like where you're on call; it's a big thing. But when it comes to things where a manager wants to get a hold of you straight away, from a trust point of view, that's where I think things fall down. And you're questioning, like, okay, why does this person need to get hold of me at 7:00, 8:00, 9:00, 10:00 o'clock at night? And should I be available?

We build by the day at thoughtbot. And so when I find, not when I find but when I talk to people, and they say, "Oh, I was still working at 7:30, 8:00 o'clock," I will say, "Why? You're devaluing your own time at that point because we're not billing any extra for that time. So you're making your craft and your skill...you're cheapening it. And I want them to relish the skills and competencies that they have. That's a big thing for me. We're very lucky at thoughtbot that we can draw a boundary at the end of the day and go, okay, that's it. There's no expectation for me. It is much more difficult at product companies.

But yeah, I think it's something that as an industry, and it's a bigger thing as a society, especially with younger people coming into the industry who have never worked in an office and may never work in an office, that idea of where is the cutoff? For so much of the pandemic, the people I would get concerned about the most are the people whose beds I could see behind them because I'm thinking to myself, you spend at least 16 hours a day in that same room.

And that's going to become the norm for people. And if people don't have those rest periods and those breaks and aren't given the opportunities to do that by their managers, then it's not going to end well. And happy people and fulfilled people do the best jobs from a business point of view. But that's never the way I approach it, but that's what I say to people.

STEPH: I think that's one of the biggest mistakes that I made early on in my career, and even now, I still have to coach myself through it. It's like you said, we are creative people and people in software and in general and not just developers, but it's a creative craft. And I wouldn't step away to take breaks. I just thought if I pushed hard enough, I would figure it out, and then I could get done with my work because I was so focused on getting it done versus the doing, as you'd highlighted earlier.

I haven't really thought about it in that particular light of focusing on this is the thing that I'm working on. And yes, I do want to get it done, but let's also focus on the doing portion of it. And so I wouldn't step away for walks. I wouldn't step away for breaks. And that is something that I have learned the hard way that when I actually gave myself that time to breathe, if I gave myself a moment to relax, then I would come back refreshed and then ready to tackle whatever challenge was in front of me.

And same for keeping a magazine that's near my desk; I have found that if I keep a book or something that I enjoy...because, at some point, my brain is going to look for some rest, like, it happens. That's when we flip open Twitter or Instagram or emails or something because our brain is looking for something easy and maybe a little bit of like brain candy, something to give us a little hit.

And I have found that if I keep something else more intentional by my desk, something that I want to read or that I'm enjoying, then I find that when I am seeking for something that's short that I can look at, that I feel more relaxed and fulfilled from that versus then if I go to Twitter, and then I see a bunch of stuff, I don't like, and then I go back to work. [laughs] And it has the opposite effect of what I actually wanted to do with my downtime.

I love the sound of this book. We'll be sure to include a link in the show notes because it sounds like a really good book to read. And I've also worked on improving the setup with my phone and notifications, where I have compartmentalized all the work-related apps into one folder, and then I keep it on the third screen of my phone.

So if I want to see something that's work-related, it's very intentional of like, I have to scroll past all of the stuff that matters to me outside of work and then get to that work section and then click in that folder to then see like, okay, this is where I have Slack, and Gmail, and Basecamp, and all the other things that I might need for work. And I have found that has really helped me because I do still have the notifications on my phone, but at least putting it on its own screen further away from the home screen has been really helpful.

ROB: Do you find that you still get distracted by that, though, when you're in the flow of doing something else?

STEPH: I don't with my phone. I am a person who ignores my phone really well. I don't know if that's a good thing or a bad thing, [laughs] but it is a truth of who I am where I'm pretty good at ignoring my phone.

ROB: That's a good skill to have. If there's any phone in the room and a notification goes off, my head swivels, and I pivot, and I'm like, oh, yeah, some dopamine hit over there that I can get from looking at somebody else's notification.

STEPH: I have noticed that in the other people that I'm around. Yeah, it's that sound that just triggers people like, oh, I got to look. And even if you know it's not your phone like you heard someone else's phone ding, it still makes you check your phone even though probably there's a part of your brain that recognizes like, that wasn't mine, but I'm still going to check anyways. And I have worked hard to fight that where even if I hear my phone go off, I'm like, okay, cool, I'll get to it. I'll check it when I need to. And I'm that person that whenever apps always ask me, "Can we send you notifications?" I'm like, no, you may not send me notifications. [laughs]

Something else you said that I haven't thought about until just now is the idea that there are some people who have never worked in an office or may never work in an office because we are leaning into more remote jobs. And that is fascinating to me to think about that someone won't have had that experience. But you make such a good point that we need to start thinking about these boundaries now and how we manage our remote work and our home life because this is, going forward, going to be the new norm for a number of people. So how do we go ahead and start putting good practices in place for those future workers?

ROB: One of the things, as we've hired people from a remote point of view who've only worked with thoughtbot remotely, is the idea of visibility. And I don't mean the visibility of I want to see when somebody's working but maybe the invisibility of people. Because you can't see when people are taking breaks, you assume that everybody is working all the time, and so then you don't take those breaks. And so this is something we saw with people who we hired in the first six months of being remote. And they were burning out because they didn't realize that other people were taking breaks. Because they didn't know about the cultural norms of how we worked at thoughtbot.

But people who had worked in the studio would know that people would get up and have breaks. People would get up and go get a coffee from a coffee shop and then have a walk around. They didn't know that that was the culture because they bring the culture from other places with them. But then it's much harder to get people to understand your way of working and how we think that we should approach things when you are sat in isolation in a room with a screen. And that's something that we've had to say to people to break that down.

And even things that we took for granted when we worked in a studio where somebody would get up and ask somebody if they could pair with them even if they weren't on the same project. Somebody might have more Elm knowledge or React Native knowledge, or Elixir knowledge. And you'd get up and say, "Hey, can I borrow some of your time just to go over this thing, to pair?" And everybody would say, "Yeah, yeah, I can find some time. If not now, we can do it later." And recently, we've had people saying, "Oh, is it okay if we pair across projects? Is it okay if we pair with other people?" It's like, "Yeah, pair."

One of the big things we say is that we have this vast amount of knowledge across thoughtbot, across the world that we can tap into and that you can use. And that's just one example of how do you get those core things that you take for granted and help people understand them? Because you don't know what people don't know. And it's all about that implied knowledge. So that's something that we learned. And we try and say to people and instill in them about yeah, take breaks. You can pair with people.

There are people who bring in culture from other places with them. But then, to go back to where you started, how do you start with people who have no culture with them or have the culture of coming from maybe from school, or university, or from a different industry? How do you help those people add to your culture but also learn from your culture at the same time? Big people problems.

STEPH: Have you found any helpful strategies to normalize that take a break culture?

ROB: One thing we tried, but it doesn't last very long because people are lazy, is putting it in Slack saying, "I'm going for a break." And you can do that, but it's so artificial. After a week or two weeks, people just stopped doing it. It was through conversation. We have a regular retrospective as the Launchpad II team where we talk about what is working, what isn't working. And we have such a trusting environment where people will say things along the lines of this isn't working for me, or I feel like I'm burning out. Then we will talk to each other about it and figure out where it comes from.

And it's a good point to raise that I don't think we have explicitly addressed it. But it is something that we will address. I'm not going to say could address; we will address it. I will talk to our latest hire, Dorian, who I have a one-on-one with next week, and to kind of talk to him about it. And we should maybe try and codify that in our handbook somewhere so everybody can learn from it, at least start a strategy and a conversation. Because I don't think it is something that we do talk about. It's the problem of being siloed and being remote and time zones as well.

A lot of stuff that Launchpad I knows Launchpad II doesn't necessarily know because we only have three, maybe, hours if people are based on the East Coast where we overlap. I have meetings with Geronda, who's our DEI Program Manager, and she lives in Seattle. And so sometimes I'll talk to her at 5:00 o'clock, and it's 7:00 o'clock in the morning for her. And you have different energy levels. But yeah, so we spend time to try and figure out how we work together.

STEPH: Yeah, I like that idea of highlighting that we take breaks somewhere that's part of your expectations as part of your role. Like, this is an expectation of your role; you're going to take breaks. You're going to step away for lunch. You're going to stick to a certain set of hours in terms of having like an eight-hour workday with a healthy lunch break in there. I think that's a really good idea.

On the Boost team, I have found that people have adopted the habit of not always but typically sharing of, like, "Hey, I'm stepping away for a coffee break," or "I'm having lunch. Maybe like a late lunch, but I'm taking it," Or "I am stepping away for a walk." You often see later in the afternoon where there are a number of people that are then saying, "Hey, I'm going for a walk."

And I feel that definitely helps me when I see it every day to reinforce like, yes; I should do this too because I already admitted I'm bad at this. So it helps reinforce it for me when I see other people saying that as well. But then I can see that that takes time to build that into a team's culture or to find easy ways to share that. So just putting it upfront in like a role expectation also feels like a really good place to then highlight and then to reinforce it as then people are setting that example.

ROB: One thing that Nick Charlton tried to introduce was a Strava group. There's a thoughtbot Strava group. So you can see if people are members of it that they've been walking and things like that. It was quite an interesting way to automate it. I think it fell off a cliff. But it was something that we did try to how can we make the visibility of this a little bit easier? But yeah, the best thing I've seen is, like you say, having that notification in Slack or somewhere where you can see that other people are stepping away from their keyboards.

STEPH: Well, as you mentioned, solving people problems is totally easy, you know. It's a totally trivial task although I'm sure we could spend too many hours talking about it. All right, so I do have one more very important question for you, Rob. And this goes back to a debate that Chris and I are having, and I'd love to get you to weigh in on it. So there are Pop-Tarts, these things called Pop-Tarts in the world. And I don't know if you're a fan, but if you were given the option to eat a Pop-Tart with frosting or a Pop-Tart without frosting, which one do you think you would choose?

ROB: That's an interesting question. Is there a specific flavor? Because I think that the Strawberry Pop-Tart I would have with frosting but maybe the chocolate one I have without. I know there are all sorts of exotic flavors of Pop-Tarts. But I think I would edge towards with frosting as a default. That's my undiplomatic answer.

STEPH: I like that nuanced answer. I also like how you refer to the flavors as exotic. I think that was very kind of you [laughs] other like melon crushed or wild flavors that they have. Awesome. All right. Well, I think that's a perfect note for us to wrap up.

Rob, thank you so much for coming on the show and for bringing up all of these wonderful ideas and topics and sharing your experience with Codespaces. For folks that are interested in following your work or interested in getting in touch with you, where's the best place for them to do that?

ROB: Yeah, thank you so much for having me. It's been fantastic to have a chat. If people do want to find me, the best place would be on Twitter. So my handle on Twitter is @purinkle which I understand is hard for people to maybe understand via a podcast, but we'll put a link in the show notes so people couldn't find me more easily.

And that's probably also a good time to say that I am actually trying to find a development team lead to join our Launchpad II team. So we are looking for somebody who lives in Europe, Middle East, or Africa to join our team as a developer and manager of two to three people. There's more information on the thoughtbot website, and I do tweet about it very, very often. So feel free to reach out to me if that's of any interest to you.

STEPH: Awesome. We'll be sure to include a link to that in the show notes as well. On that note, shall we wrap up?

ROB: Yeah, 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: Byeeeeee!!!!!!

ANNOUNCER: This podcast was brought to you by thoughtbot. thoughtbot is your expert design and development partner. Let's make your product and team a success.

Support The Bike Shed