#1 - Remote Work

Have you ever wondered what it’s like to work away from a tall office building in a large metropolis? Courtny and Den dive into this topic and more in the inaugural episode of The Work Item podcast!

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Den: Right now it says it’s recording, so I think we’re good to go with “Courtny and Den Talking,” season one, episode one. We have to have a season. I have a… I have a feeling that this is going to probably be a long-term project so…

Courtny: Go seasonally. Break like…

Den: Any show, right? Like, you you watch a show on Netflix that are seasons - season one, season two, like for us, I don’t know, twelve episodes a season? Twenty four episodes a season? Once a week, once a month - whatever it will be.

Courtny: The season of figuring out what in the hell we’re doing.

Den: Yeah, no, that’s exactly what the season is about. I mean, that’s the idea of, you know, “Courtny and Den Talking”. That’s the name of the show. So I like the working title. So what are we going to be talking about today, Courtny? What’s the… What’s the topic?

Courtny: So today we’re going to just discuss a little bit about remote working. And it’s a topic that has really come to the forefront of many people’s minds recently. With the outbreak of the coronavirus and all the news around workplaces shifting their workforce digitally. Remote work’s been around for a long time, so there’s been contractors, there’s been companies that have been kind of leading the charge and working remotely for quite awhile. I mean, I know Stack Overflow for a fact has been doing this for ten plus years, roughly that, but I’m sure there’s other companies and freelancers, for sure, that have been doing this much longer. Freelance web developers and engineers.

Den: Right. So tell me more about kind-of… what do you do? I think that this is kind-of… We should start with intros, ‘cause a lot of people probably watching this or listening to this have no idea who we are. Why are we talking about remote?

Courtny: Yeah, do you want to go first? Go ahead.

Den: Sure, yeah, no. So, I’m Den. I’m a senior product manager at Microsoft, and I’m driving some of the docs.microsoft.com user experiences. So I’ve been working on technical documentation for now, what is it, like… I started in October 2015, so it’s about… Going on five years now in documentation, about six years at Microsoft, out of which three years were remote. So I moved to Canada not too long ago, three years ago, and I’ve been remote ever since. Same team.

Courtny: How was that transition for you?

Den: It’s… It’s jarring. Not going to lie. It was a little bit of a “What the heck do I do?” Kind-of when most of my team is actually in Redmond, and I’m the only one that moved to Vancouver, and it was very jarring because I had to figure out a lot of these remote best practices. You know, reading articles from Jason Fried, David Heinemeier-Hansson, and you know they’re talking about all these remote best practices, and I, you know, at the time I was reading a lot of those, like this is nice. This is all remote work. But then when I actually started being remote, like oh maybe I should re-read that, and actually put it in practice. It was totally new, it was such an adjustment period. It took me probably a year to figure out how to do things the right way. How did it go for you? Because you’ve been remote for quite some time?

Courtny: Yes, I’ve been remote… It’s been about seven, eight years now. I started… I started at an agency called Universal Mind, and they were… They had many remote contractors, many remote freelancers that they worked with, but I was actually a full-time employee and the way the organization was structured is they had basically a user experience agency. And my background, I’m… In my day job, I’m a product designer, so I work with Den at Microsoft, building and designing products, and mainly doing visual, UI, user experience work. But Universal Mind is kind of where I cut my teeth on remote work, so they had had some experience doing this in the past. When I came into the organization, so they were prepared to have a remote worker. The interesting thing was that they actually had… Their user experience studio was in Grand Rapids, MI, so there were 15-16 designers in an office, and I was the only full-time that wasn’t in the office, so that started to become more and more of a problem, the longer I was there. So what happens is - you have this, like, tribe there in Grand Rapids. And there are conversations that you’re left out of. Wasn’t a huge deal when it comes to maybe a particular client, because you were kind of siloed on a client project. But when it comes to professional development or networking with fellow designers, that can become an issue.

Den: So how did you build a network? I’m just purely curious since you talked about that, because that’s a challenge that a lot of remote workers have when you’re not in the office and most of the people are in the office. How do you do that? What worked for you?

Courtny: I guess… I will also add that I’m located in Indiana, so I’m in the… I’m actually in the middle of nowhere, in farm country, Indiana and there’s not a lot of opportunity to connect. The biggest city is Indianapolis, so if I want to travel to a conference, usually I try to go there, or Chicago. But honestly, it’s just kind-of maintaining a really good strong virtual presence. That’s what I’ve always put a lot of emphasis on, both in my networking through Twitter, things like LinkedIn. Not a lot of… Not really a whole lot of in-person things, honestly. If I have a chance and I go to a conference, obviously yes, I’m going to try to make good connections with people, but I think you probably know this, when you go to conferences, there’s so many people in there, there’s so much going on. It’s hard to build a deep relationship with anybody, right.

Den: Right, yeah.

Courtny: And a good conversation, and that’s it.

Den: Yeah, I think conferences to me. It’s a lot of times I see friends that I already know, like yourself, I see my coworkers, but it’s rarely where I’m in the kind-of mode of “Oh I’m expanding my network to so many new people that will kind-of closely work with me through the short, long-term,” whatever that might be.Do you ever go to things like meetups? I hear a lot of people talk about, you know, if you have a big city around, you can always go to a meetup on startups, or Python, or ML, whatever your interest is, do you ever go to those?

Courtny: I used to. So probably six or seven years ago. That was like my main way of, you know… I would get out and I would go to local… The local design events, and I would try to present, make some… I did make some good connections. So actually guy I work for at Microsoft, right now he was a connection from an in-person event that I went to, so I wouldn’t say that that was totally like, that’s not the way I do things today. I think that people are a lot more socially active on Twitter now and I definitely use those avenues to participate. So a lot of people hold like meet… Like Hangouts. I can join somebody that’s holding an AMA, and they’re doing a hangout format like this, right? And I can just join it. So I think that the world, the tech world has definitely moved more towards having a virtual presence, being able to interact that way, being able to connect a network that way. It is not just being entirely in-person, conference-driven.

Den: Right, and I think even the recent events are showing us that a lot of times you will be forced to have these remote events, or remote conferences, or remote meetups, because it just… I feel like it’s even more inclusive, because then you get a larger audience that can participate, right? Not everybody can fly into a city. Not everybody can buy a ticket and go and pay for the hotel. First of all - it’s online. Anybody can come in.

Courtny: It’s fascinating to see of the last three years things shift this way. With the rise of Discord, Slack, and now Teams, so people are able to create communities, digital communities, that are just basically chat rooms right? They’re like IRC chatrooms, back in the old days you would have an IRC client and you could chat that way.

Den: Oh gosh, that was a long time ago. IRC, it was like 10 years ago when I used IRC last. It’s still alive, right?

Courtny: I was in middle school and early high school, so this would have been like the year 2002.

Den: My gosh, remote connections before remote connections, talk about that.

Courtny: So there was a… There was actually a World of Warcraft IRC group that I cut my teeth.

Den: Oh my gosh, I totally missed out on that. I always went to MSN Groups that were like “Harry Potter Fan Club,” and I would sign up for those. But that’s not even close to instant responses, more like a forum, which I think in this case kind of. That’s the predecessor of the offline conversation, kind of asynchronous communication. And forums, actually, if you think about it, forums are excellent for remote work because you post a message and then you wait for a response. That’s kind of what Stack Overflow does with answers, right?

Courtny: Yeah

Den: You’re not randomizing people, it’s…

Courtny: Or, you know, Jeff Atwood’s project Discourse, that’s kind of built around… His idea there is building a better forum for doing that, like it’s not necessarily a forum.

Den: Right.

Courtny: It’s made for conversation. So…

Den: Right.

Courtny: Yeah, I think that having those tools become more accessible right, the onboarding experiences are easier. It’s easier for people to just download and get going using those products, so we’re just seeing this kind-of Eden emerge outside from the scope of tech. You know, I’m seeing it even in my wife’s work place - she teaches at, or she works at a K-12 school and they’re using Teams, and it’s kind-of changed their workplace, because they’re not, you know, tied necessarily to just email all the time. It’s actually like a gathering place. It’s a watering hole, right? It’s a digital watering hole. So yeah, back to your original question about networking. I really feel like it’s important as a remote to make sure that you are maintaining a great digital presence. And you’re curating it, right? You don’t… You’re staying active, and you’re paying attention to what’s going on, and you’re actually reaching out to people and you are interacting. Maybe giving them feedback on that blog post, or retweeting their tweet or something. As simple as sending them a message that you find interesting from maybe another author, right? Just letting them know - hey, I see you as a person, not just as an avatar.

Den: Right, right. No, I definitely second the part about Twitter. I love Twitter. I’m probably on Twitter more than I should be, but it definitely allowed me to connect to more people than I have ever connected to before. I think I would credit actually having my job through the power of Twitter, because I blogged something and somebody at Twitter… Not at Twitter, on Twitter, working at Microsoft, saw what I blogged and said “Hey, let’s have a conversation. Let’s talk about it.” It opens doors, and it’s one of those things where, I went to a college in the Midwest that was not a big name school. We never had, you know, big recruiting events or anything of that nature. I would have missed out on a lot of that if it wouldn’t be for Twitter. So that kind of virtual networking, and building that network beyond just the constraints of your office - I find it super valuable. So 100% with you. Speaking of which, and we talked about things, you know, forums and IRC, which is a nice digression from the topic of networking. How do you work remote? You know, we talk about asynchronous communication being one of them, which is - forums are great for it. What’s your approach? What do you do day by day? How do you structure everything you do remotely?

Courtny: Man, I’ve really taken advantage over the years of like the… It really does come down to async, that is the biggest theme on my head that I can’t get out of my head. It’s like, I try to push people to use asynchronous forms of communication. so that, one, it’s it’s more beneficial for me, so I can structure my day in a way that makes sense for both my family and my coworkers. As you know, right now I’m working for Microsoft, I’m in Indiana, so I have a three hour time delay. When we were working… When I was working on Stack Overflow, we had people in Poland, that I would occasionally work with, so there was like a six hour time gap there. You have to push your work. You have to become better at writing and articulating your ideas in writing, making sure you’re keeping tabs on where people are active. So, certain people have certain habits, certain people want to use certain tools to communicate. Every organization is a little different. You know, Microsoft is very DevOps-heavy. Stack Overflow, where I worked before, it was very Trello-heavy, so you have to be familiar with going between tools, using a mixture of tools too. Maybe it’s a combination of like Word, Word docs, right, and DevOps.

Den: I love Word comments. Just the fact that I can comment on stuff inside a Word document is so convenient.

Courtny: Yea.

Den: Instead of having a million emails, right? How many conversations just get lost when you start emailing people back and forth, and there’s a fork. And now you have 17 email threads going about the same thing. And then you have to somehow put it all together, versus just leave a comment in a Word doc, and you have this conversational structure. It’s so much easier.

Courtny: Yeah, and then you can organize those Word docs, right? Not that you can’t organize emails, but yeah, I found that it was honestly overwhelming coming to Microsoft ‘cause it’s such an email-driven org, and things are done so much through email. I’m happy to see, obviously, people adopting Teams as as a venue to communicate. So like two-way communication before decisions are made, but once it is made, it should be logged somewhere right? You shouldn’t have to be searching through a chat log or email thread.

Den: And people, I mean, people leave companies. People come to companies. If I come in and pick up a certain area that I have not been working on before, I don’t have access to anybody’s emails or chat logs. I need to, but I want to read somewhere why certain decisions were made, and this is where things like documents or anything like a Markdown file somewhere is super helpful, because it gives me context, and not having to go and ask my manager “Hey, can you forward me all the emails that you were ever on on this specific topic,” like who has time for that?

Courtny: Yeah, well and another theme that I picked up from my time at Stack Overflow was the idea of default public, and as a designer our work is obviously exposed to criticism, and you know, you’re putting yourself out there when you’re designing something. You’re trying to design a solution to a problem, and a lot of people are going to have opinions about that problem and this solution, so I found that it was actually an exercise in breaking down the barrier and like breaking down my own, checking my own biases in putting my work out there early, communicating early to a broad group of people, like my working group, but anybody can go look at it. Helps, one, make the design better, and two - find my reviews aren’t as scary, right? And they’re not as like potentially off-base, like we can be correctly tracking on the project in the design direction before it ever gets off course.

Den: Oh yeah, for sure, and then like you said, yeah, like a lot of people will have input, because I don’t know of any single feature or project that I’ve ever worked on where I was the only one making all the calls. There’s always going to be two, three, four, seven people. Our good friend and our collaborator Isaac Hepworth, from also Microsoft, from DevRel, he wrote a doc, Working with Isaac, and one of the points that he’s making is exactly where you called out. Write things down. Having things in public and available to anybody. If there is no underlying reason for that doc not to be. Because not everything can be public, right? Like if somebody makes people decisions or performance reviews, you probably don’t want those exposed to your team, because those are private. But things like feature specifications or designs, there’s no reason to put them behind the gate within your company or within your org, short of them being super-secret and relating to some secret release.

Courtny: Yeah, I mean, many times we’re working through like a new product area or a feature idea and the people closest to it, they’re going to communicate very intimately, but that doesn’t mean those conversations have to happen in a one-on-one, or like a small group message, right? It can happen in a public channel or whatever, so that other people can just kind-of keep a pulse on it and see what decisions are being made, and maybe they have really valuable insights. There’s been many times that people have come into a project that I’m working on, and they’re not directly associated with it, but they had really valuable input. And they actually impacted the final design in a great way, so I think that is also like another kind of my third pillar, which is like serendipity, right? So you’re default public. But then you’re also creating opportunities for serendipity both within your team and for your product. Your design solutions. Your ideas

Den: Right. And this is that kind of that openness… I really like seeing what other people are doing, because oftentimes, even you see what they’re doing, and you’re like, “Oh, wait, a second. This will impact my feature or my product direction. Let’s talk. Let’s chat about this” versus finding that out a month later. Once they ship, and you realize, “Oh my gosh, it totally breaks my business model” or it’s… Yeah, I’m all for openness.

Courtny: I almost imagine it, like if… I like to tell people, like when you go into an office and you see, you go into maybe a private meeting room, and you see a whiteboard filled with sketches, right? There was a really vibrant conversation here. Probably was over an hour long. But you have no idea what was talked about. All you have as a kind of artifact is this board. This whiteboard with sketches, right? Like a public chat with designs thrown in it, or like wireframes and stuff. It’s all there for everybody to see, so like it’s like being able to understand what happened in the… In that meeting room. Without you happening to be in a meeting room in that meeting, right?

Den: Right, for sure. Now, this kind of brings to the next point that I’ve experienced, and this is where you should have less meetings and just more writing things down, because I think in addition to some cultures being very email-oriented, there’s a lot of cultures that are also very meeting-oriented, and where you’re describing, as you know, somebody met, they put a lot of stuff on the whiteboard, but then nobody has the context of those decisions. You have the notes, versus when you have a document or you have an open conversation somewhere like in a private Stack Exchange instance, or something like that, you can always go through and see what people thought, what people said, and you just have more time to flesh out your thoughts, right? When you write things down, and you have to outline why I’m doing this, how I’m doing this, what I’m considering. Somebody leaves a comment and says “Hey, maybe you should reconsider this or do things differently.” Or “Redesign this,” that gives you that natural flow, versus if I open a OneNote right now and look at the notes of a meeting that I had six, seven months ago, I don’t remember who said what or why they said that, I just see the note that said, “Oh, we decided to make the button green.” But what’s the context of that?

Courtny: Yeah.

Den: I feel like just writing more things down instead of just doing meetings, which, not to say the meetings are not valuable, but I try to do less meetings and just more writing things down.

Courtny: And having more asynchronous artifacts and in conversation, invites people of different personality types, right? Because there are certainly people who are really, they really are, they can put on a performance for a meeting, or they can…

Den: That’s a good one.

Courtny: Or dominate a meeting, when in fact somebody else might really need some deep thought around an idea, right? They can’t…

Den: Right.

Courtny: They can’t take it all in, and the way that they work, that they don’t want to take it all in right? In that meeting they just want to absorb and then maybe come back to you the next day, or two days, like here’s my really deep thoughts on this issue. Sometimes I really value that over just the immediate gut decisions.

Den: Yeah.

Courtny: I’m really happy you thought this out, and came back to me on this subject with thoughtful comments and not just what would you have time for in that 30-minute window I gave you, right? For the meeting.

Den: I totally love that comment you… I think you’re spot on with this, because you always have meetings, and I’m sure you’ve been in those meetings. I’ve been in those meetings where you have one strong voice of somebody that just kind of like “I’ll be talking about everything. I have an opinion on everything,” and I know I have a fault of mine, that sometimes I feel like nobody’s talking in the meeting, I’ll talk, and what that results in is that a lot of people will essentially just kind of not respond or they will not comment on things. And giving them that time buffer, and saying - it doesn’t matter if you didn’t say anything through the meeting, just comment on the doc or send us your thoughts in a week, that’s great. That’s fantastic. Nothing needs to be decided that very moment.

Courtny: And that’s kind of an artifact too, of like when you go remote. One of the things that really is an issue, is - you don’t have body language, the presence in the room. Standing creates energy, so people… You’ll notice that if you have a group of people in the room, you’re giving a presentation, if you have everybody stand and get them active, you’ll notice how much more attentive they are, and I think that that’s maybe something that is also kind of… You have to be mindful of it when you’re a remote worker. I love that I have a standing desk, right? ‘cause if I know I’m going to get into a meeting, I need to be really active. Then I’ll stand up. I don’t know what it is, but you lose the bit of the social cues, the body language, the “Hey, I have something to say next.” And you can’t get that through, like, if there’s ten people in this chat right now, we wouldn’t know if the ninth person’s waiting to have a comment, right? Unless they told us.

Den: What do you think of, and this is a topic that I know it can be a little controversial between people, what do you think of turning the webcam on? Because I realize, to me, I’m personally very comfortable with having the webcam on. Whenever. I don’t have anything to necessarily hide or anything of that nature, but I do realize that some people might be more introverted. Some people have health issues they’re dealing with, so they can’t turn on the webcam. How do you feel about that? Just having the webcam on for remote meetings?

Courtny: I’ve always viewed it as a nice to have, right? Like if you’re going to be working with these people for years on end, try to have some… The video allows us to have a much more natural conversation than, say, not just staring into an avatar, right? Now, that being said, there might be, there are days that I turn my video off, ‘cause like I had my kids running around in the background. I didn’t dress all the way. Like I’m not going to get… I’m not going to get on the video chat, or I don’t feel like I need to add to the… There’s sometimes I’ll join in a giant meeting, and I’m just like, I’m going to turn off my video ‘cause there’s so many people here. My habit is to definitely have that video on. If it’s like, you know, a smaller group meeting or I’m leading it, right? I don’t know, it’s just a good habit. I think it’s part of curating that digital presence, the best form you can get is video.

Den: I mean, I’ve heard that from people too, when I would meet them in person, when I come to campus. And you know, they’re being “Oh you look totally different from your avatar.” It’s like, yeah, because my photo was taken, I don’t know, six years ago and this is, you know, of course I look different, and I hope I look different.

Courtny: People are always like “You’re way taller than I thought you were.”

Den: Right, exactly. It’s like, oh, or you know, there is all sorts of comments, but this is where I think having things on video just makes it so much easier, because then hey, you see me act. You see who I am. I’m a person. I’m not just some avatar, and I’ve seen an avatar where people put Sponge Bob as their avatars. I feel like I’m talking to something, like I don’t know who this person is, right? It’s like - it’s Sponge Bob.

Courtny: That’s one thing that, like I said, if you’re working, if these people are your coworkers, try to make an effort to be at least like a human being. Don’t be like some anime character or, not that… I love anime, but I’m saying like…

Den: Yes, yeah, I want to see a face, right? No, for sure. I feel like sometimes it’s just confusing because I don’t know if I’m talking to the right person, because I see like an animated character, and then I was like “Oh wait, a second. Oh yeah, now I know who this is,” so it takes me a second. So, talking about all these things, I think another thing that I do want to call out are some of the kind of… or I don’t wanna call them mistakes, but maybe some things that some people don’t understand about remote workers. Let’s chat about that, because I feel like there is a little bit of that chasm between remote and non-remote workers, that oftentimes people don’t fully internalize what’s it like to be remote. So kind of, what are some misconceptions or misunderstandings of a remote work? To me, the number one that stands out is the time, or the fact that like “oh, if your remote you’re watching Netflix all day, you’re playing video games.” Because, work from home, right? At home is your Xbox or your PlayStation, and everything is there, and it’s definitely not that. I feel like it goes into the opposite spectrum where people start working more because you have no clear, kind of that boundary between “I’m in the office/I’m at home” versus you’re kind of always in the office.

Courtny: Yeah, if you ask my wife I am always in my office. She’s like “You need to get out of the office” and I think it’s very important that your leadership communicates that like, you need to take a break at some point and you’re not always readily available. I think another thing too is, coming from a place like Stack Overflow, that’s where I previously worked, they were remote first, so everything that they would do in the office, every piece of equipment, every type of benefit that those workers would get, remotes get too, so remotes are not second-class citizens. They’re treated like everybody else. They get the same availability for equipment, right? Like a standing desk, a nice chair, same like equipment requisition if they want it. But also factoring in things like, hey, if we’re having a meeting, you have to set up the meeting in a way that it’s accessible for remotes, so having a video chat attached to the meeting invite, making sure that if you guys are doing a summer party, you know, remotes also have the opportunity to to go do their own thing, so they get $50 and they can go out and take a day off or half-day off and then go have their own summer party. So, I think that’s like a leadership thing, right? Like, don’t treat your remote workers as second class citizens and make sure they have all the same types of opportunities that a full-time employee would have in the office.

Den: Yeah, the meeting comment resonates with me because, more than once where I would join a meeting, and I’d be the only one on the call. And then 20 minutes later they were like, “Oh wait, you’re the only one that is remote. We forgot to call in.” And they’ve talked about a bunch of stuff ahead of time, and it’s not the most pleasant feeling, honestly. But you see that shift, kind of, where more people started working remote or more people are distributed, where, I know you are remote, I’m remote, a lot of the design team often times works remotely, a lot of the PM team works remotely, and then you see that transition of - now everybody gets in this remote mode of work because you’re kind-of forced to and your team is distributed. Your core partners are not in one place and that kind of puts people more… To be more aware I guess, is the way to put it?

Courtny: Yep.

Den: But yeah, that totally makes sense. Other things, I think that people mistake, you know, remote workers, is the fact that, oh, if you’re if you’re remote, that means that you’re always going to have things that distract you around you, which is not always the case. There’s people that can work remote from a co-working space. There’s people that work remote from an isolated room, or soundproof room or whatever that is. Remote doesn’t equal that, you know, you’re always disturbed by people, you were sitting in a cafe sipping your latte or anything like that. I feel like that’s very common when I talk to people, it’s like “Oh, so you probably have all these things around you?” No, I can still focus. I can still focus pretty well. I have my focused space. I have my way to get into the zone. I don’t know. It’s actually… To me, it’s easier, because I don’t have distractions from people stopping by my desk and saying, “Hey, can I bug you for a minute now?” I’ll answer in my own time.

Courtny: And there are certain personalities that… I don’t do well in an office environment because I just want to hang out and talk to everybody. So honestly, for me, the isolation almost helps. I’m very social, so again - I can really do focused, deep work for a large chunk of time, right? I’m talking two to three hours of just work, which is wonderful, right? You can get a lot done in that amount of time. I think another thing that remote employees that have to be mindful of is that you need to also make some concessions and be ready to… Maybe there is, it’s not the best or most opportune time, I’ve had many calls that are West Coast time. I’m on the East Coast. I have to take the call - it’s going to be later in my evening. I just make room for that, right? I do that chore. I try to take care of whatever it is I was going to do at that time of day early in the day. So kind of shifting around your schedule, but making some room to take important calls and be willing, I guess, to adjust your schedule a little bit too.

Den: Right.

Courtny: Just some flexibility, give and take with your coworkers.

Den: Right, where you know, there’s cases where, for example, we work with the team in China and our 5:00 PM is their start of day. So there’s going to be some compromises where you need to meet at 6:00 PM. You need to meet at 7:00 PM, but that’s also not… I want to look at this, this is not the rule. This is more of an exception, because this is where your idea of asynchronous communication and writing things down, this is where it plays in very nicely, when you have those kind of time zone discrepancies. And you realize that some people need to take their kids out of school. Some people need to take care of, you know, going to the doctors office or anything of that nature. Where, if you write things down, a lot of these problems, I don’t want to say go away, but they’re mitigated, they’re mitigated much better than just having to meet. And I realize that sometimes you have to meet face-to-face. I love face-to-face communication with people, but it’s easier when you have structure around it.

Courtny: On that note, I think it is very wise, once again, kind of speaking to, if you’re looking at scaling up your remote workforce and you’re trying to plot like, well, how is this going to work out? Absolutely critical to get everybody in the same room, you know, once or twice a year.

Den: Right.

Courtny: I can’t tell you how important and how beneficial Stack Overflow meetups were, or just as a venue to get to know your coworkers. It was never very productive to try and get work done during these. They were genuinely like “Let’s get all these people that are really smart together and let’s see what happens. Let’s see what type of relationships they build,” and that is a really strong catalyst for motivating your team, getting right-sided about, kind of rallying around something like “Hey, we have our meetup, this is going to be awesome this year.” And yeah, just the team spirit and camaraderie and getting to know who you’re working with because it can get lonely and it’s really nice to be able to spend time with your coworkers.

Den: And you just have the opportunity to learn more about different sides of them, right? Because for me, you know, you didn’t know that I play certain video games before we met in person because this is like… It just doesn’t come up in a call to discuss some design reviews, right? We don’t talk about “Oh, have you played the new Diablo?” I don’t know…

Courtny: Or that you snowboarded, right? I didn’t know that.

Den: Yeah, exactly, or the fact that you’re working with kids and various schools and you’re coaching track, right? This is a huge part of your life and these are the things that you would just not get to know about people short of talking to them in this informal setting.

Courtny: Yeah, there’s no way, like, yeah, I’m a college track and field coach. There’s no way that I would be able to do that and work at Microsoft, probably. The opportunities would never align. I would never be able to be a coach at Wabash College and work at Microsoft.

Den: Right.

Courtny: Or have the time to, like, colocation - they’re not even in the same state, right? So it just creates a… Again, it’s like a tag along benefit. It’s like all these little moments are able to be created just by the fact that I’m remote.

Den: So how do we convince more, you know, you talked about the benefits. A lot of companies are still hesitant to remote, right? There’s… We talk about bigger corporations that, when you talk remote or not, in the office that is… That’s a scary world for a lot of people, because now you don’t have people in the office, now you don’t have the opportunity to go directly to their desk or, you know, their cubicle. I feel like there’s a number of things that remote still opens up opportunities towards, that compensates for the fact that people are not in the office. So we talked about, you know, before this meeting, where there is definitely a positive effect on the environment, right? If you’re commuting less - less exhaust. So if you have companies that do care about the things like climate change and things like the effect on the environment - there you go. Just having a remote workforce minimizes that significantly.

Courtny: Think about your taxes. My taxes go to the town that I grew up in that would otherwise not have had me, so reduces the idea of what they call “brain drain.” These smart, intelligent people. I’m not saying I’m smart and intelligent. What I’m saying is…

Den: We all are… Well, let’s be realistic.

Courtny: We’d leave the community, right? The people that you need to stay and keep a community going don’t leave. So a lot of our smaller communities are aging. This generation’s aging because their children and the people who who really should be taking over the reins are moving to big cities and growing those urban centers. So I think that that is really exciting, that remote work can enable people to stay, maybe, where their birth family is, where they… Traditionally they’ve been around, right? My wife has… Her parents have been farming this area for a long time. We’re going to take over that farm someday. Once again, not possible if I lived in Washington so, yeah, I think that there’s like obviously too, the tax based thing, there’s the fact that a home in Indiana is only $150,000, 3 acres of land, 2,500 square feet. That’s a benefit to me right, and to my children. So yeah. I think, back to your original question, how do you start convincing these companies or how did companies start moving this way? But it’s really hard when you’re on a hourly billing cycle. You’re tracking little tiny hours. It’s like, yes you can do remote that way and I did do it that way when I was at Universal Mind, billing to a client. But the clients understood - hey, these workers are distributed. They’re going to be available in different time zones and so you just have to set that expectation. Can you trust your workers? That’s the second thing, is it a trust issue? Do you feel like the people that you have employed are, one - necessary, and two - are they getting the job done? Are you setting clear expectations for what needs to be done? I think anybody who’s given a remote position has a ton of responsibility to get their shit done. Get your stuff done, but it’s actually a motivator, ‘cause if you get your stuff done you have more time for the things you love to do.

Den: That’s the big difference between tracking time spent on a problem versus tracking impact, right? Because you can spend 2 hours on a problem and have tremendous impact versus somebody that spends 8 hours in an office and doesn’t have nearly that. And I’m not saying that somebody that works in an office has less impact. It’s absolutely not the case. But just valuing the impact by time spent seems to be a little off, right? Because at the end of the day, it’s like if I get things done, does it matter where I am getting those things done? Probably not. And I mean, and also the thing that, you know, talent is everywhere. It’s not just those hubs, and you have sometimes talent that just cannot move for some reason. Somebody’s taking care of their parents. Somebody is, you know, their kids are in school and pulling them out of school is going to add a lot of complications to their life. They can’t move. They can’t relocate. Do you just miss out and pass on that talent and just say “Sorry we cannot hire you?”

Courtny: We’re an innovative and cutting edge company, but we only hire within 30 mile radius of our city.

Den: Right, exactly. And the thing about it too, is with the modern technology… I mean we have Teams, we have Zoom, we have Slack, Hangouts - you name it, there’s tools to make the connection easy. I realize that there’s probably the challenge of broadband Internet and kind of the broadband penetration is not quite equal yet in North America, or even, you know, Eastern Europe, for example, where I’m coming from - a lot of the population doesn’t have access to Internet, if you’re in some village somewhere. But it’s getting there, and the the barriers of entry are getting slowly removed, and you have more of the opportunity - better Internet, you have the tools, you have the tools that are inexpensive. There are tools that are free. Use Skype, I don’t care, that open these doors, so we no longer have the excuse of saying “Oh, it’s hard to do remote because we can’t connect people.” You can connect to them anywhere.

Courtny: I will ask you this question. I know you’ve only been remote for about three years, but, do you think there’s any difference in terms of years of experience? So I think there’s certainly… My internship perspective or experience taught me a lot, and it was an in-person internship, it was basically an apprenticeship. Or, sorry, I learned everything that I know about programming from there, it got me my start in my career. I think I couldn’t… I probably would have had a really hard time doing that remotely, honestly.

Den: Oh for sure. Yeah.

Courtny: My question for you is - do you think that it’s more of a challenge for companies that are having younger talent or junior people, right?

Den: You know it’s a good question. I thought about that and I think this is where I will say that remote is a valuable tool, but with that little asterisk on it, that says it depends. Where, things like internships, just like you, I did my internship in-person and I found it tremendously valuable to build those relationships with people, especially when I didn’t know what I’m doing or how I’m doing things. I needed somebody to almost, I don’t wanna say hand-hold, but to show me the ropes and just explain how things work, going to a meeting with a VP and present my stuff, and see the feedback, see how they react, how they think - that was tremendously valuable. So I would say for… Definitely for junior employees, for people in college, having that in-person internship would probably be way better than remote. I would say, if you have the chance to do that, that would be so much more valuable. That said, I still think that if somebody doesn’t have the opportunity to do that, you know, in-person… So, for example, say somebody is trying to get an internship from some other country, like in Eastern Europe, where I mentioned, where I’m coming from, and it’s very complicated because you have to worry about things like visas, you have to worry about things like the cost of the ticket and oftentimes some internships don’t pay for relocation, some internships don’t pay for housing or anything of that nature. It has a lot of complications and when your internship is in-person only, that is also excluding a lot of talent, essentially, versus when you remote, you can say that by having regular meetings with the individual, by having regular sync-ups to understand what was blocking them, if they have any questions and see how that works, I don’t think it’s impossible to do remote. I do think it’s easier and much more efficient in-person. It will give you much more experience, so I would prefer that.

Courtny: I would echo that last train of thought because in my experience with younger designers it has been quite a bit more hand-holding remotely, so I have to create more documents. I have to create more stand-ups, right? There just needs to be more… You have to be a lot more proactive, as, like the person managing them. To make sure that there’s clear expectations set, we know when we’re going to talk and kind of just basically making sure they don’t feel like they’re wandering aimlessly, right?

Den: Right, right. No, I mean, and I mentored interns in Redmond while I was here in Canada, and just having that conversation with them about what’s blocking you, what are the things that I can help you with, turning on the webcam and just seeing their reaction to the conversation and how they think about certain problems is not impossible. I would say it’s definitely, you know, it depends. If somebody would ask me - would I prefer an internship in-person? Absolutely. If that was not an option, would I take an internship that is remote? Yeah, 100%. I feel like it still can be valuable and it can still bring in a lot of experience, regardless of where you are.

Courtny: Yeah, and I think it definitely makes it more accessible to people who maybe don’t have the means. You gave the example, and maybe somebody just does not, you know, they’re not in the area.

Den: Right. So let’s talk about the things that you’re describing, where you’re not in the area - do you think there would be people from Indiana that wouldn’t be able to take an internship in-person? Because I know there’s a lot of people from here that wouldn’t be able to do that.

Courtny: I’m not sure, I think that somebody young and in that position would probably try and put themselves out there and make it work, but you’re asking a lot, right? Maybe they have a, I don’t know, like a fiance that’s going through nursing school, but I don’t know, it is like having the option, saying we did this with a recent hire. We said “Hey, you can work remote.” He was a junior designer. You can work remote or you can go in the office. We don’t really care. You know we’re remote-first, remote-based but yeah, we’ll give you an office space, and he actually was like, “Alright. I’m going to move out there and I’ll make it work.” So for him that was important to be there in the Microsoft office, but yeah, I would say… I think there’s certainly scenarios where people might not, you know, they would think it’s awesome that they can do a remote internship. There probably needs to be better mentorship and guidance, and best practices put in place. I think that we’re in the early stages of remote, really catching on, and a lot of the remote positions - they feel like they’ve been for very senior or well-tenured people, right? And now we’re starting to see this younger generation be exposed to working remotely. Actually, my sister-in-law, her first job out of college was remote. She was a remote social media advisor for Ascension Health, and this job actually ended up not being what she thought it would be, because she wanted to be in the office, right? So I think there’s definitely those type of people too, that they want the social interaction. I think it’s great to have both.

Den: Yeah for sure. Yeah this is not like… Our talk is not about “Everybody should be remote forever and cancel the office leases.” It depends on what you’re doing, and there’s a lot of jobs that cannot be done remotely, and especially for somebody that’s working within those offices that is helping with things like building maintenance. Not every job is remote-friendly, so this is not something that we can blanket say “You know, everybody in the world will be remote in 10 years.” That’s just not possible.

Courtny: Waste management can’t be.

Den: Right, exactly.

Courtny: Welding. You know, you can’t be a welder. There’s like a lot of trade jobs that can never be that way…Tech… I kind of… I’m not sure, maybe on-site server, manager or something? I don’t know what that would entail entirely, because a lot of the tech jobs can move that way.

Den: You’re right. I mean, if you’re working in a data center and there’s a faulty hard drive that needs to be replaced, we don’t have robots to do that. Not yet anyway, so you know, and it’s… You wouldn’t be able to do that remote. There’s somebody that needs to be there in the data center that has a quick response, where you don’t want half of your product to go down because hard drives are failing left and right, and it’s like “Hey, wait like 3 hours before somebody gets there.” Somebody needs to be working there. So there are some constraints, and it’s totally understandable where not every company might be ready, but speaking of which, we can wrap up our conversation on future casting as you describe. I love that term - future casting. Where do you think remote work is going to be in the next, I don’t know, let’s… What timeframe do you want to talk about? Like is it five years? Ten years?

Courtny: I really feel like within five years the major players in the tech sector are going to be largely remote-first, at the very least remote-friendly. So I’m talking Google and Facebook. You know they’re kind of already making strides together - Facebook, or Microsoft definitely heading in that direction, IBM… I think a lot of these companies are going to start to realize, hey, we can get some really good talent and it’s going to be a lot more competitive. Amazon even, they traditionally aren’t really open to it, but I think they could see them moving that way too, so…

Den: That’s a good prediction, yeah, I like it.

Courtny: It’s interesting though, because like you would think that they might be leading the charge and they aren’t. It’s been companies like Stack Overflow. It’s been companies like Basecamp, right? These smaller startups that have proven that model can really work.

Den: And Basecamp has been absolutely fantastic. I mean, if you are looking for a company that is the role model for remote work, that’s them. I can’t think of any other…

Courtny: They’re building tools for it, and they actually hire their workforce, whereas somebody like Slack - they’re building tools for it, but their whole team has to be in San Francisco. Same thing with Discord, the Discord app. They’re an amazing product but you have to be in San Francisco to work there.

Den: And I mean, for people that worry about, like “Oh, if you’re remote, you can’t build great products.” GitHub - I mean, GitHub is built mostly by a remote workforce and look how many people in the world use GitHub. Right? It’s a fantastic product. There is so many jobs within it that it would be, you know, nobody would say that you can only build in an office. Absolutely not. No, I like the… I think it definitely resonates with me that more companies will go remote, especially with kind of the crises that are happening right now around COVID, and any other health issues or natural disasters. People start realizing…

Courtny: Like we talked, I touched a little bit of housing cost. It’s like every time I’ve looked to move, I’ve been approached by companies or look to move out there. I’m just blown away. I just can’t fathom it. It’s almost hard for my brain to wrap around how expensive everything like property is there. So I think that that’s too, people have to weigh that. When you’re talking to talent, and they have to weigh, “OK, well, you’re going to make me move from my nice place here to some place that’s really crowded. And it’s super expensive. You know, that’s not my lifestyle.” Like everybody is different.

Den: Yeah, for sure, it’s like - do you buy a house now or do you buy a house in 10 years, I don’t know? Depends on what your life priorities are. But also where you live does dictate a lot of those decisions. So yeah, I think it’s also in, you know, in a couple years we’ll see more teams being more open to the idea that remote workers are just as trustworthy as somebody that’s not remote. And just putting their trust in knowing that even though you might not have the meetings in person, even though you might not have the conversations next to somebody, next to somebody’s office, you’re still going to be productive. You still going to be able to get things done and add value to the company or the project, or a team. Whatever you’re working on, because I feel like right now there’s still a lot of that hesitation where you know, it’s like, “Oh, I don’t know, I don’t quite know if I’m gonna… I’m ready to hire somebody remote.” And I think it’ll start thawing - that ice of “No, no, absolutely not remote. You have to meet in person,” it’ll get better.

Courtny: It’s almost like a company has to have the champion, or the one person that’s in that leadership position that’s able to say “Hey, we’re going to start making this a priority. We’re going to try it first to be remote friendly, and then we’re going to remote first.” I think that it does kind of happen in phases, if you’re an established company.

Den: I mean, look at our work.

Courtny: And the habits of it.

Den: Yeah, I mean, look at our work, right? Like DevRel at Microsoft. Look at all the developer advocates. Pretty much all of them are remote. Yeah, some of them have offices, but they’re working all over the globe and they’re fantastic.

Courtny: And then our product team is going more this way to, right?

Den: Absolutely.

Courtny: We’re probably one of the first within the company that’s moving that way. So I think that’s pretty cool too.

Den: And I can only hope that this will just spread more widely and we have more and more remote people because, I mean remote does open up a lot of opportunities. I love being remote. To me - I was scared of it at first, but the more I work remote, the more I realize like hey, actually I love it. I love the flexibility. I love not having a commute. I love being able to manage my time as I need to and not be constrained to being in a physical location. Can you imagine if you have, you know, “Oh I need to go and deal with a car repair, I have to deal with like 3 hours of commute back and forth until I get to the car from the office.” But instead I can just go from home, get it done, come back and be right back to work. So it’s actually it’s a win for the company because I’m wasting less time and I’m available much quicker than I would have otherwise.

Courtny: Not having to deal with commute, you get that time back. You’re able to spend it with your family, where you’re able to spend it taking care of yourself, like getting a workout in instead of spending that hour drive to where you’re going.

Den: Which I think… This is kind of, we can wrap up on this very important point - when you work remote, don’t forget about the fact that, have work-life balance. It is very easy to slip. It’s very easy, kind of, what we started the podcast on, the fact that you can start in this mode of like “Oh, you know, I’ll wake up, I’ll get to work,” and then before you you know it, you look at the clock and it’s 10:00 PM. The day has gone. Have those boundaries, have those limits of saying “I’m remote, but then I clock out at 5 or at 6,” whichever the time is where after that you’re not doing work. You have to shelve it for the next day.

Courtny: Shut it off. Yeah, it’s hard I mean, there are times that I can… You know, my computer is in here beckoning me, I need to go. I need to go see what that thread is about and I think you caught me there the other night, I was online working. Who knows why? Like at 9:00 o’clock at night you don’t have anything else to do but you know, that’s also… Maybe that’s a benefit to an employer. Get some extra production out of me that they wouldn’t have expected.

Den: But the flexibility of hours, where during the day you can take, you know, one hour to take your kid to some practice somewhere, but then you’ll compensate that one hour later. It’s not a zero sum game.

Courtny: And another thing that I would like to talk about too. I know we’re kind of getting to the end here, but it’s sick days. Everybody has sick days, and I think it’s funny because when I tell people that we have sick days even when remote, my father-in-law’s like “You have sick… You can just work straight through a sick day” and well if you’re sick, if you’re genuinely sick, you probably should just rest. Take advantage of your sick days even though you are remote, and I’ve caught myself doing that too, where I’ve worked through a sickness. It’s really not worth it. Just take some time off. Use your sick day, get better.

Den: Right. Because health is like… Help burnout, mental health, and making sure that your physical health is in good shape. It’s up to you to manage it. Don’t have your laptop by your bedside where you can wake up, read email, go to bed with your laptop on, you’re reading email. It’s just not good. It doesn’t help anybody.

Courtny: No, no. Know you have a significant other. Doesn’t make them happy either.

Den: Oh yeah, for sure. Well, this is a good conversation. I think this is nice try for our very first episode of “Courtny and Den Talking” so we’ll see what kind of reaction we get to this. And hopefully we’ll get to talk more about remote work, and maybe we’ll even have some guests.

Courtny: Yeah, that’d be awesome. I will also have my fancy camera then too. I’ll hook that up.

Den: Nice.

Courtny: We can talk a little bit more about equipment that time.

Den: Yes, that’s a very important topic that I think deserves its own episode. Just equipment, because there is just so much out there.

Courtny: There’s a lot of awesome stuff out there. There’s a lot of people doing some really cool stuff, so…

Den: I cry for my wallet already. Well OK, we can talk about that the next time then. So thanks all for listening and we’ll see you in the next episode.

Courtny: Later.