Jeff Robbins interviews Josh Gross, CEO of Planetary, about where to hire specialized remote workers, the value of over-communication and tricks for competing with conventional companies during the sales process.

Here’s the transcript:

JEFF: Hi everyone. It’s Jeff Robbins, back with Episode 78 of the Yonder Podcast, where we talk to company leaders and big thinkers, about how to make remote work. We’re focused on expanding the remote work job market, and helping listeners to create happy, productive, distributed teams. On this episode, we are talking to Joshua Gross, who is the Founder and Partner at Planetary, which is a small digital products agency that does work with large clients like Google, Amazon and Univision. They’ve got a small team of really talented people. Really great conversation with Josh. We talk about a new place to hire specialized remote workers. I’ll leave that a mystery. Just listen to the podcast and find out where you should be posting your jobs or maybe if it’s the appropriate place for you. The value of over communication and tricks for competing with conventional companies, particularly during the sales process.

JEFF: Hi Josh. Welcome to the Yonder podcast.

JOSH: Hey, thanks for having me.

JEFF: Yeah, thanks for coming on. Let me start with the question I ask everyone. (3:28) Where are you talking to us from today?

JOSH: I’m actually talking to you from South Carolina. I actually live in New York, but my partner and I came down to South Carolina to visit some of her family. So, we’re down here for a few days and actually heading back up to New York later today.

JEFF: Nice. See, you can work from wherever, and do podcasts from wherever, too. (3:56) So, tell us about Planetary and particularly your relationship to remote work around that.

JOSH: Sure. I’m the Managing Partner and Founder of Planetary. Planetary is basically a digital studio. We work with a lot of clients, large companies, startups, to help them do digital product development. That can be anything from building an internal analytics app to building out a complete new website and E-commerce platform for food brand which we’ve done at least once, if not twice. [laughing] But, the type of work we do varies really widely, but we mostly focus on working with web technologies and on mobile to using web technologies to build mobile apps. We’ve been around for about six years and we’re a small team. We are based all across the world.

JEFF: Your website is really cool. It’s not often that I say that about websites, but having run a web development company, I appreciate that. [laughing]

JOSH: [laughing] I wish I could say it’s easy, but that was a process.

JEFF: I can imagine it was. I’m just looking at it, horizontal scrolling and it’s got these images that flip back and forth, at least on the desktop version it’s doing all sorts of cool stuff. Congrats on that. [laughing]

JOSH: [laughing] Thank you. It was a painful process. You should’ve seen some of the earlier versions of that. I’m happy where we are, let me put it that way.

JEFF: (5:52) Simply just making your own website for your own company that does digital work, there’s some voodoo in there somewhere that it just prevents it from happening. There’s that old saying about the Cobblers children have no shoes, but I feel like the universe is stacked against the Cobbler in that case. You would think he’s busy doing work for other people, but, you know, he wants to make shoes for his kids, it’s just not happening.

JOSH: You’re your own worst client. You want to make the shoes for your kids, but you want to make them perfectly out of the best material, you want to put them together with the perfect stitching. Who has time for that?

JEFF: No, it’s impossible. And you also have a product have you’ve built (6:46) It helps distributed teams.

JOSH: Yes. Spacetime.

JEFF: (6:54) Tell me about Spacetime.

JOSH: It was actually born out of a need that we had as a distributed team. We’ve been distributed since we began, day zero. As we grew and we started hiring folks, some of our earlier folks were in Eastern Europe, South America, we had folks across the world, and keeping track of when they were available was difficult to say the least. We kept forgetting when they were in, we kept bothering people late at night. So, we had at some point discussed, we had an internal team hackathon and we were like ooh, what would be fun to build? One of the things that came out of that was a tool that lets us see when folks are in, when folks are out and what time zone, they’re in. So, we built it for ourselves to solve a problem. As I showed it to folks a couple months later there was more interest than I expected, so we kept rolling with it as we had time between client projects to build it into something that other folks could use.

JEFF: (8:13) This is the surprising, biggest challenge of starting a distributed company, I think, for lots of people. You think, oh, we’ll just start a distributed company. We’ll hire people all over the world, but I feel like understanding the concept of time zones and even just the basic idea that the sun is in different places on the planet at different times [laughing] is something that our animal brains just don’t get.

JOSH: No, not at all.

JEFF: So, it’s like everyone I know that’s started a distributed company, it’s a surprise or maybe it’s not a surprise, but it’s something that they instead try to really avoid. We’re just going to hire people in the greater Minneapolis area. I had a podcast recently with someone, kind of in a good way, hired people who were one flight away, which is a nice strategy, but you’re not totally benefitting from the unlimited talent pool that you could get with a fully distributed team.

JOSH: Right. The tighter the radius you’re looking in, obviously the fewer folks there are that will fit the needs that you have. Basically, making it an unlimited radius, you can select from anybody, but you do have that challenge of dealing with time zones and for whatever reason, humans are just really bad at doing time math. It’s not inherent to anybody.

JEFF: Yeah. It’s a difficult thing to get over. Whenever I get a team, we run the Yonder conference, and this Yonder circle now, where we get together people who are thinking about remote work, and I always want to talk about time zones and everybody kind of rolls their eyes. But, I’m like, “No, you don’t understand. Time zones are a big challenge. We all need to figure this out.” Ultimately it comes down to the scheduling and the different rhythms of people in differing time zones. (10:39) Do you have people all over the world?

JOSH: We do. Right now, we have folks in South America, East and West Coast of the US and Canada and in Western Europe as well. So, not as distributed as we have been in the past, but still enough so that time zones can be an issue.

JEFF: (11:01) So in the past have you had people in Asia or Australia?

JOSH: We actually have not gone that far, but the furthest person we’ve had is Romania, which is far enough in and of itself that fortunately that particular person enjoyed working later hours, but had they worked a normal day, we would’ve only had a couple hours of overlap.

JEFF: When the hours that people are sleeping is the hours that we think of as the workday at least in the U.S.

JOSH: Right.

JEFF: Having as many tools as possible [laughing] around that, it’s really difficult. You got this vernacular for talking about time. “Hey, are you free for lunch tomorrow?” “Hey, maybe we can talk at 9:00 tomorrow morning.” That just don’t have meaning when you send an email to people and you’re not quite sure where they are.

JOSH: That becomes such a problem. I’ve even gone so far as to look up folks when I send them an email. If I’m suddenly talking to a client, I’ll look up where they are by searching their name and hopefully, they pop up on LinkedIn and have their location, so I don’t feel like a complete jerk when I suggest a time and they’re in California, and I suggested basically something that’s like six a.m. for them.

JEFF: Yeah. It’s funny. I think people that work remote, particularly on LinkedIn and places where you might find their location, are a little less likely to post their location because it doesn’t matter, I’m wherever, except when you want to schedule a call with them and they’re in the middle of sleeping.

JOSH: It’s funny. You mentioned people roll their eyes when you talk about how important time zones are. I had a conversation with someone the other day, they were trying to introduce Spacetime to their team, and it’s one of those problems that it seems like folks don’t know they have until they experience not having it.

JEFF: Right.

JOSH: He’s telling me their team loves complaining about how difficult it is to schedule meetings, but was also hesitant to start using Spacetime because, oh, we don’t need another tool to manage this. He’s like, “Well, I guess they’d rather just complain than not have this problem at all.”

JEFF: Yeah. It’s this funny thing. Again, it seems to be outside of how our brains want to think. So even the idea of talking about it [laughing] is sometimes the thing that people don’t want to do. They don’t think it’s a problem until it is a problem and then when it is a problem it feels like it shouldn’t be a problem.

JOSH: But it’s like how do you solve it? How do you make it go away in a way that doesn’t require thinking about the time zones and putting that mental effort in.

JEFF: Right. We can all use the UTC time but that seems to be a challenge. [laughing]

JOSH: I don’t know if you remember this, but this was from years and years ago, Swatch had Swatch time.

JEFF: [laughing] Yes.

JOSH: And that was like, they were trying to physically invent the UTC as a timestamp.

JEFF: But then it was something funny. It was like an hour was not 60 minutes, it was 100 minutes [laughing] or there were 10 hours a day. It was something weird like that. It was Swatch beats, the number of beats per day.

JOSH: It did not stick. I remember they actually released watches that exclusively told the time in beats, which I thought was very funny.

JEFF: Yeah. (15:12) I think I had a watch that you could put it in that mode, so I put it in that mode for maybe about an hour one time and looked at my watch. I was like, this means nothing to me. [laughing]

JOSH: It’s funny, because it’s like that idea has clearly been around. People hate time zones enough that this watch company tried to invent an entire different unit of time to eliminate it. Poorly, but even within a company that makes watches for a living, I was like time zones are awful.

JEFF: Honestly it was probably well thought out.

JOSH: [laughing] The idea was good. Right?

JEFF: It was well reasoned. [laughing]

JOSH: Everything’s a unit of 10, sort of like metric, but then you try to sell it in the U.S. market and everybody’s like, I got my 12 inches. I got my 144 pounds of gross. Like, what’s the problem here?

JEFF: The problem as usual is the Americans. [laughing] We’ve got enough people. We’ve got enough commerce. We’ve got a big enough country where it’s like ahh, it’s fine the way it is.

JOSH: Sixty minutes in an hour. Sixty seconds in a minute. Who needs anything more simpler than that?

JEFF: (laughing) Right. (12:27) You say the companies been distributed since day zero, and you’ve got a very prestigious company. Your website is beautiful. You’ve done some work for some amazing clients. I’m imaging that you have a very talented team. Talk to me about the decision to be distributed or the non-decision [laughing] and how it’s been to build a team and find talent.

JOSH: It’s definitely been interesting. It was not really a decision that was made intentionally at first, honestly.

JEFF: That’s often the case, especially with small businesses, whether they’re distributed or not, you sort of do what you do.

JOSH: It was like a matter of convenience, honestly. When we got started, Planetary is born out of, what I was doing at the time, six years ago, which is freelancing. So, when I started getting to the point where I needed additional help, rather than trying to find folks in New York or Brooklyn, I knew that was going to be expensive, and I didn’t have an office at the time, I was mostly working from home, I just went online and found some folks I could work with. I got introduced to a friend of mine who lived in St. Louis at the time, a designer, he was helping me out, also living in St. Louis, it was just easier than trying to find and pay someone in New York. When I realized it was not that big of a deal to have folks in different places, it was like, alright, what’s the difference if I have a team of people in New York or I have a bunch of people in different places?

JEFF: (18:25) You said six years ago is when you started all of this?

JOSH: Yeah. We got started, in earnest, in 2013, so it was six and a half years ago at this point. It was March or April 2013; I want to say. I was doing freelancing for several years before that, so it was like this slow curve upwards into doing bigger projects.

JEFF: That’s great. How many people do you have these days?

JOSH: We’re seven.

JEFF: Smaller businesses tend to grow a little bit more organically. It’s people you know, people you meet, stuff like that, as opposed to as we think about larger companies, kind of recruiting people and needing to have more of a proactive hiring. (19:52) Which mode are you more in? Is it that earlier one? Are you hiring people as you meet them around on the internet? Or, are you actively out recruiting people? [laughing] Whichever of those it is, I’m curious to know how that works for you.

JOSH: When we got started, initially the first couple of folks I was working with were folks that I got introduced to through some acquaintances. But, once we started hiring, honestly, we just put up some job postings for the role we were looking for and started to interview folks, and these weren’t people we knew, before they sent us an email with their resume. We just kept rolling with that. The first person we hired was based out of the UK somewhere. We were rolling with the punches at that point, so we put together an interview process for an engineer. We had never really done that before, but we rolled with it. I talked to some friends that had done hiring in the past, got a sense of what’s the right way to interview a person for this role, and we went through a bunch of interviews with different folks, and brought somebody on. They worked with us for two, two and a half years, and that was a good start for us.

JEFF: (21:40) So, where are you posting jobs? What does it look like to hire for you?

JOSH: That’s always been hard for us. When we first started posting jobs, we tried all the typical job boards. Mind you, six years ago we didn’t have all the remote working job boards that you do now, so we were posting in the places you would post any sort of job. The number of applicants we got in and the quality of the applicants was a struggle initially.

JEFF: Struggle because it was so many applicants, right?

JOSH: It was just overwhelming. There were hundreds of people sending us emails and being just a couple of folks routing through all these resumes, it was exhausting to say the least. The process was a lot more difficult than I was hoping it would be. I was really hoping for a smaller set of more qualified candidates that fit the role better. But we ended up finding actually AngelList job board and posted there, and for whatever reason we got fewer applicants, but they were all much more qualified for the role we were looking for; the type of person we were looking for.

JEFF: That’s really interesting.

JOSH: Ever since then, honestly, I’ve posted any openings to AngelList job board and the folks we get from there have been great. That’s basically where we found everybody, we’ve hired that hasn’t been a referral.

JEFF: (23:21) Do you feel like posting on AngelList was better because the candidates were looking for something specific or that there were just fewer of them? What about that?

JOSH: I want to say it was a combination of both. There were definitely fewer candidates looking at that job board. It has always been, at least as far as I can tell, a smaller job board. It doesn’t attract as wide an array of candidates, but the folks that are looking on there, are looking for something very specific.

JEFF: They’re kind of expecting jobs with more specific qualifications which honestly is probably what you’re looking for.

JOSH: Exactly. And you can narrow down by those qualifications. AngelLists filtering platform is designed and tailored specifically towards tech rolls and it makes it a lot easier to narrow down candidates that you want with specific experience or in a specific role. It’s just a lot easier than some of these more generic job boards that cover every possible role in lots of different fields.

JEFF: (24:39) Are there specific traits that you’re looking for? Are there specific skills that come around this being a remote job?

JOSH: It really depends on the role. We don’t play the game, necessarily that they need to be a culture fit, and everybody needs to have the same personality. Our team right now is composed of folks that, one of our folks makes himself golf clubs as a side business, and one of our other folks just bought a farm and has horses. These are very different types of people and I think that’s really healthy. It really depends on the role. I think the biggest thing is just the ability to communicate. That’s the most difficult part of being a remote team, so that’s really the only aspect that is the most important. You need to be able to communicate well and clearly, since we’re all not sitting in the same room together.

JEFF: I think that’s a thing we inherently look for in a job interview. Especially when you’re interviewing someone remotely. I think oftentimes with our tendency to want to be fair. Maybe that’s what we think we’re being. We want to judge people more on their resume and the jobs they’ve had in the past and maybe they didn’t interview very well. But, look at what they can do or what they’ve done. The truth is with a remote job, especially in a fully distributed company, that interview, that communication [laughing] is a test of their communication skills that they’re going to need in conducting this job. Right? So, if you’re not connecting with them in the interview it kind of doesn’t matter what their resume says they can do, it’s going to be a little cordoned off by their inability to communicate.

JOSH: Yeah, that’s the most crucial part. Any of these other skills can be learned or you can get better at them. If you’re a Project Manager, you can get better at project managing. If you’re an Engineer, you can learn to be a better engineer. But, learning to communicate better I’ve noticed is more difficult and as a remote team if you don’t have it from the get-go, at least some level of ability to communicate well, it’s a struggle, because then that person really doesn’t feel like a part of the team simply because they just don’t participate in everything the rest of the team does in the same way. It also just hinders other folks. You need to be able to communicate as an engineer, especially on a remote team, what you’re doing or what problems you’re having. You need to be able to have little hesitance to reach out to somebody else on the team and ask for help and talk to them about the problem you’re having, or what you need, both over a text or over a call or jumping on a video chat. You need to communicate what you need clearly and easily as opposed to sequestering yourself off in a corner and trying to solve a problem because you don’t want to or can’t communicate the thing that you need.

JEFF: Yeah. And there’s a certain courage and vulnerability willing to allow for vulnerability which to some extent has to do with company culture, but it also has to do with how comfortable people are being able to ask for help, being able to admit when they’re having a difficult time. I’ve seen that be a problem too, where, you can hire people who are good at communicating their wins, their successes, but tend to get a little bit shy when things aren’t going so well, so they tend to do a thing I call submarining, where they’ll disappear [laughing] for a week or two at a time because they were having a challenge with a project. But that has this sort of compounding effect, particularly for anyone who’s managing them, of like, I think that they’re having trouble and they’ve disappeared. [laughing]

JOSH: And you don’t know what trouble they’re having because they never told you.

JEFF: Exactly. “I don’t know how to help. I don’t know what to do.” And they disappear which is bad. This is bad.

JOSH: I’ve only had that happen once or twice in the past few years and it’s tough. Especially as a remote team, because you’re not there standing in front of them. You can’t get the to talk to you in the same way.

JEFF: Yeah. When people need your help, the most is when they’re the least likely [laughing] to ask for it in those cases. So, you have to build this in as part of the way that your business does business.

JOSH: Yes, exactly. Everything I’ve told my team over the past few years, like, one of the core tendons of how we work as a team is just over-communicate. Say more than you think you need to, because that’s probably the right amount.

JEFF: I like that. Just over-communicate. It’s a mantra. [laughing] You need to over-communicate that your company needs to over-communicate. I know I keep saying this, but we need to over-communicate. [laughing]

JOSH: Exactly. It’s funny because my team I say some of the same things over and over, either in one on ones or to the rest of the team and they’ll start repeating these things back to me, with an eye roll, but at the same time in my head I’m like, “good, you get it.”

JEFF: You got it. [laughing]

JOSH: I’m going to keep saying it, but you know it. [laughing] It’s just that that’s so crucial to say more than you think you need to, because worst case, you’ve given too much information but that’s not necessarily a bad thing, but if you don’t give enough information then people have to start filling in the blanks.

JEFF: (31:17) And that’s, I guess I call it dangerous. Just people are filling in the blanks and they don’t know, so it tends to be this multiple reality. In worst case scenario, this is what’s going on with this person. We’re not hearing from them because horrible things, they’re in rehab and they’re hesitant to tell us. [laughing] Or, best case scenario they’re just really heads down and really kicking ass and are just going to have this big reveal a week from now. But usually the worst case is not true either.

JOSH: You don’t know unless they tell you. You just don’t know. It’s so much more helpful. When you fill in the blanks you also end up with a situation where folks are either guessing what they need to do to help you, or guessing what work they need to do along side you and then what ends up happening is a lot of times you end up doing the same thing that they were already working on because you didn’t know you’re duplicating their work.

JEFF: Yeah, which I think is almost the stereotype model for how I think collocated managers, when they think about how remote work is bad, [laughing] or could be bad, it’s this, it’s that, how am I going to know what work people are doing? How am I going to trust that they’re doing the work? How and I going to keep things optimized, productive and efficient when I’m trying to coordinate all these people that are spread out and not communicating. [laughing] Because maybe we don’t need that level of communication in a collocated office, so we don’t expect people to offer that.

JOSH: Right.

JEFF: But it’s really necessary to making a distributed teamwork.

JOSH: Oh yeah. We have this issue with our clients sometimes. I’ll be talking to a potential client about a project and I tell them we’re a distributed or remote team, and then they start making faces and getting worried, like, “Oh, well how will you manage the project?” “Where is everybody based?” “What if we have a question?” I’m like, “nothing changes here. We work the same way any company that is all based in New York would work,” but I have to explain to them, “no, no, no, everything will be fine. We’ve done this for years.”

JEFF: And even if you’re a New York agency working with a Fortune 500 business in New York, they’re never going to come to your office. You always go to their office anyways, and it almost looks exactly the same except that you get a couple hotel rooms every now and then. [laughing]

JOSH: Right, and I’m gonna say it just doesn’t cost anymore at the end of the day for them, but, like, “I’m happy to show up at your office and talk to you if you want to see a live human being in person,” but by and large the majority of this work is going to be over phone calls anyway, whether we were based in New York or not.

JEFF: Right, and as we were talking about earlier, they’re working with better communicators.

JOSH: Oh, yeah, exactly.

JEFF: Or at least people who have a requirement to be better communicators. [laughing]

JOSH: Yes.

JEFF: [laughing] I’m not saying people in collocated offices can’t be good communicators but there’s a threshold for doing remote work.

JOSH: The only thing I think about that is we built processes around how we communicate and how we communicate with clients and how we document things. So, when clients are working with us, not only do they get folks that can communicate well, or require to communicate well to do the jobs, but we will document much more than I imagine other agencies do, or from what I’ve seen, other agencies will document, simply because in order to communicate between teammates we need to have a lot of information written down. But to the benefit of the client, that means we have a lot more to share on a regular basis.

JEFF: (35:38) This idea, it comes up less and less, and I’m curious, because when I started Lullabot, my company, back in 2006, we certainly weren’t to a tipping point. I still feel like we’re not quite to a tipping point yet, but, talk to me about the legitimacy of being a remote team. You’re saying that sometimes you’re able to get the project [laughing] but once you start to get in to get the project they go, ”Oh, your teams all over? How’s that going to work?” How often do you hit that attitude? Are there tricks that you found to avoid that? I mean, having a great website is probably [laughing] a good trick. They can just see. But, do you have any insights for people who are afraid that they might hit that attitude, that challenge?

JOSH: It’s tough. Honestly, it’s tough. We’ve run into it less and less I would say. We definitely run into this problem much less frequently then we did five years ago pitching clients. It’s less important but you still do run into it. The best thing I found to (37:08) those fears is offer to have someone show up on site for these folks. The people that have the most hesitance about working with a remote team, I’ll often say, “I’m happy to fly out there,” if they’re based in California or whatever. “I’m happy to fly out there and drop in and say hi for a couple of days and work with you on site. We’ll do a couple of workshops, or I’ll send one of my engineers out to you and they could sit with you in the office for a day and get the project kicked off.” I’ve noticed that kind of comforts them, having seen the person, or at least one of the people on the team, and met them and getting a sense that there’s a body behind the camera; there’s legs below the fold. It helps a lot. Once you get that, you get past that fear of the team being remote, that’s the best solution I’ve found. But, everything else, it’s hard. It’s hard to sell your way past it otherwise.

JEFF: Yeah, I think you have to have your marketing really buttoned up. You have to have your brand, have a really good website. But then, as you say, sort of having empathy for what people in a collocated environment might value. For instance, getting together in person, that’s something that you certainly do, and maybe even working it into the sales process where it’s like, “Hey, let me show up and shake your hand,” [laughing] and help you to realize that I have legs.

JOSH: Exactly. [laughing] That’s my favorite thing to tell folks.

JEFF: The value of legs.

JOSH: Yes. There are legs below the camera. I’ve made this joke, even within our team. Everybody has met each other except for I think one of the folks we hired last year, since we haven’t had a meet up since, but, it’s like, “I don’t know if you have legs below the camera and if you do, you do, if you don’t, you don’t,” but for me it’s not that important. For clients it somehow has value; that has value.

JEFF: The thing I always, sort of notice having seen this happen in a number of environments, but particularly with my own company, people, when you have a company retreat are oftentimes particularly surprised by how tall or short people are.

JOSH: Yes. Oh, yeah. That’s been an interesting thing the couple times we’ve had a team retreat. I’m particularly [laughing] short. I’m only 5’5” and then meeting some of my teammates I was like, “Oh, cool. You’re all taller than me. I am the shortest person here. “Everybody just look down when you’re speaking to me for the rest of the time we’re here. Don’t worry about it.”

JEFF: Using that as part of your hiring process or something like that.

JOSH: Yeah, exactly.

JEFF: You’re inadvertently trying to hire people who are taller than you are.

JOSH: [laughing] Yes, we have a hire requirement. Everybody needs to be under 5’5”. I can’t be the shortest person of the company. It is definitely one of the funnier things that you experience when you do a team retreat, it’s just like, “Oh, you’re all much taller than I would’ve expected because I’ve ever only seen you sitting.”

JEFF: Yeah. (41:05) So, do you have people get together? Do you do team retreats once a year or more often? Do you have any philosophies or thoughts about when people need to get together in person, what role that plays in a distributed company?

JOSH: We haven’t done one this year, we’ll likely do one next year, but the first few years I wouldn’t say we were too small, it was we were just financially constrained, so we didn’t hold one for the first three years of the company. But once we got into a place where I felt comfortable doing it, we did a couple of them two years in a row, and it’s really helpful. Doing one once a year is really valuable to get folks together. There’s a level of team building comradery, whatever you’d like to call it. There’s things, I’d hate to admit there’s things you can’t get as a remote team while being remote, but there’s something about being able to see everybody in person and chat in person that really does help bring everybody closer, and you get to know people in a way that’s sort of an outside of work, happy hour type of situation for a couple of days. It definitely helps bring everyone together. Everyone gets more comfortable with each other. Then you go back to work, but it helps improve the dynamic. Everybody learns things about the other teammates that you wouldn’t normally have discussed over just your day to day Slack chat.

JEFF: Yeah. I always feel like working in a distributed team, it doesn’t feel that way necessarily, but is very cerebral. There’s a lot that you need to be proactive in your communication. You need to be good at communicating. They’re all good practices. It’s better ways of communicating. Better ways of managing. But getting together in person is not cerebral, and after all this cerebral time connecting with people, it’s really nice to have more of a, physical connection. Physical connection means a lot of things and some of them are not what I mean, [laughing] but it’s this primal, just to be able to sit with people and oftentimes you’re at places, so you’re sitting around a fire. Like, we were like connecting with the caveman connection. We’ll just grunt to each other for a bit. It’s wonderful in building trust and more emotional non-cerebral connections, which really enhance the other side of things once you start back to work.

JOSH: I think you get a sense of the persons other personality, that you don’t get in a day to day context of working remotely. Even over video chat, there’s a way you square yourself up with the camera and the way you talk on camera is different, than you would talk just sitting on a lawn chair around a fire. There’s a different body language that you have, and you get a sense of someone’s personality just sitting there with them in person, than chatting with them with a screen in between you. That’s really, I think, the biggest benefit of having these team retreats, is, being able to get a sense of what someone’s personality is like and getting a clear sense of what this person just likes and doesn’t like, and how they are in person, because when you speak to them, when you go back and put the screen back between you two, it helps, I think, give you a better sense of how you talk to this person and how you interact with them.

JEFF: Yeah, it really gives you context, a much more high-fidelity experience of understanding people. (45:23) Have there been any epiphanies, insights, or little tricks you’ve picked up along the way that anyone who’s listening might be starting a company and thinking that distributed might be a good way for them to go? Any advice that you might have for them?

JOSH: I could think of two things. One being, document as much as you can in a shared location. For example, we use Notion to document everything from how we run the team to when we do certain things to our notes for our standups. Everything goes into one place and it’s a great way to be able to just have a record and collection of all these little tidbits, important facts, information you want to reference later, and especially as a remote team, especially if folks aren’t working all the same hours or there is some overlap, but you might say something or have a task that needs to get done for somebody coming in the next morning, having all that documented in one common space is wildly helpful. It makes everybody’s life a lot easier because you know where to look for the information that you need. The other thing I’ve noticed, which is less serious, is just come up with something fun to do with the team once a week. We recently started doing this, but on our Monday, we do a standup every Monday, and I’ve added a question of the week to it and the question of the week is like, if you were a hotdog would you eat yourself? Something ridiculous, but it’s fun to get people’s answers because it just sort of loosens everybody up after coming back from the weekend and you’re shaking off the weekend head space. It brings everybody back together and you get some really goofy answers as everybody’s having their first sips of coffee.

JEFF: (47:27) [laughing] Yeah, well, I think if we look at this remote working as more cerebral, it’s nice to find ways to loosen that up and make sure that there’s less purposeful communication that’s happening, and conversation that’s happening in ways that we can just talk about the weather, or our kids, or whether we would eat ourselves if we were a hotdog. [laughing] But things that get us outside of that purposeful work communication. The thing I say all the time is, there are all of these books out there that talk about how to have efficient meetings and how you should ahead of time have a bullet point list of the meeting agenda that you send out to everyone who is going to be there and then everyone shows up exactly at the right minute and within 30 seconds of the top of the hour your into the first topic and hopefully you’re done within 10 minutes, and I feel like if, on a remote team, if that were all you were doing, you would never have any human connection with the people that you work with. So, finding opportunities, and it might be that first five minutes of each meeting, is just, how’s everybody doing? What’s going on? What’s on your mind? Including the, “oh, I got a flat tire on my car,” or “it’s raining here.”

JOSH: I feel like that’s been such a crucial part of building some of the team dynamic, is that, we do Monday morning and Wednesday morning standups and having those first few minutes just be a loser conversation, like, “Let’s go around and everybody talk about what you did this weekend,” or “How are you feeling? Are you present,” is a really nice one that just shakes people up and get’s people to be like, “I’m here, but my kids not feeling well so I’m a little distracted by that?” There’s a human element that you add to those conversations. It helps.

JEFF: Being able to admit that. Can you imagine in a lot of stereotypical corporate culture is there anyone to admit that they weren’t fully there? [laughing] You’re all sitting around a conference table and it’s like, “Hey, how’s everybody doing? Are you here?” And someone would go “I’m really not here, I’m just totally distracted.” [laughing] It seems like it would not fly in certain environments, and yet I feel like you really need to embrace that. The whole human. And acknowledge that people are going to ebb and flow knowing that they will flow eventually, they just may be ebbing now. That’s okay.

JOSH: Yeah, and it’s like it’s fine, people are human. Not everybody is going to come into work at 100% everyday being totally present and totally ready to do everything they need to do. It’s just not practical. People have lives outside of work and as much as people try to avoid letting it affect their work, sometimes it does. One of the folks on our team, she has a farm and she has horses, and she threw her back out doing work and came in the next morning and was like, “Yeah, I’m here, but my back hurts so I may or may not be as focused as I normally would be.” I was like, “that’s fine.” It’s better to know that and be like, “Okay, cool, we won’t ask as much from you today as we otherwise would.” But that’s not a big deal. That happens.

JEFF: And it does happen. Again, I’m trying to listen to the podcast [laughing] as we’re recording it. Through the years of a more conventional manager who is hearing this and saying, “What? You’ve got somebody who is basically not going to work today? How is that possible?” I think again in this distributed work environment you need to judge people more on their output rather than input. You judge them on the results. Are they getting the work done and then trust them to get it done? It allows us to have these conversations about the difficulty of getting work done, and the ebbing and flowing of productivity, and all that kind of stuff that we might not otherwise talk about.

JOSH: It’s exactly that. As long as they get their work done, it doesn’t matter if they need to take a couple of hours off in the middle of the day to lie down. It’s not a big deal. One of our engineers takes off for an hour in the middle of the afternoon to get outside, because he lives out in California, and wants to get some fresh air before the sun goes down. But he comes back and he gets his work done. He works an extra hour in the evenings. It’s not a big deal as long as the work gets done. Honestly, as a manager, if you think that every single person on your team comes in at 100% everyday and is just pumped to get all of their work done, you’re lying to yourself.

JEFF: Or they’re lying to you.

JOSH: It’s not a thing.

JEFF: It’s like, “Yeah, I’m going to totally get all that work done,” and then you walk by and Facebook is open on their screen [laughing], and, you know, “oh, I’m sorry, this has only been up here for a second.” I came up with this phrase on a recent podcast, and I’m going to just keep revisiting it because I think it’s good. Eventually we’ll get it printed on a T-shirt. But monitoring is not managing.

JOSH: Yes, I like that.

JEFF: (53:51) I think when we think of this, ultimately it goes back to the industrial revolution of monitoring employees is the same thing as managing employees. Are they there? Are they sitting? Are their hands moving? But, it’s really not the same, especially these days. Going to a much more supportive coaching role where we’re helping people ultimately manage themselves.

JOSH: It’s more about giving folks the direction they need to go in. Setting the goals then keeping an eye on exactly what they’re working on at any given moment. If you’re doing that, as a manager, I don’t know how you manage to get anything else done that’s more important. It’s like that element of micromanagement, where you’re just constantly keeping an eye on every single thing that’s being done by every single person you manage, and it’s like, “Don’t you have other things that are more important for you to be doing? Shouldn’t you be thinking about what’s next?” As opposed to what is presently being done.

JEFF: Yeah. And what you’re being judged on as a worker is not whether you’re doing the work, but whether you look like you’re doing the work [laughing], you’re going to put more work into looking like you’re working than actually working.

JOSH: There’s something nice about the remote team that I can’t see what anybody’s doing at any given moment. I don’t care.

JEFF: There’s no way of looking like you’re working. [laughing]

JOSH: I can’t care. No, for all I know all these people are sleeping for seven out of eight hours and then get all their work done in an hour, but honestly if they’re that good, great. More power to you. It’s great. All I have to worry about is, is the work getting done? What’s the output we’re getting out of the projects? Are things being done on time? Everything else is irrelevant; I can’t see it.

JEFF: [laughing] I agree. Well, this is a great conversation Josh. (55:53) Is there anything you wanted to touch on that we haven’t touched on? Or anything you thought of in all of our conversation here?

JOSH: Not really. I’m excited to see, as more teams go remote, that folks get less fearful of working with a remote team. I think that’s a matter of time, as more teams are going remote, and it’s now become a thing. Four or five years ago, it was really not a thing folks were excited about. I think some of that fear is fading and it’s nice to see. I think that we’ve still got a ways to go and I’m excited to see it become more of the norm as opposed to an outliner.

JEFF: Yeah, I get both excited and a little bit afraid of it. [laughing] When Fortune 500 companies are teaching six Sigma practices around remote work, ultimately that’s good stuff and I do feel like a lot of the stuff we talk about, the allowing autonomy, sort of accepting the whole person, allowing people to work more flexibly, is par for the course. That’s the way that remote work works. So, maybe it’ll be a matter of seeing companies start to accept that stuff rather than taking remote work and making it less fun. [laughing]

JOSH: Yes. You don’t need all of these consulting methods on top of remote working. It’s just about trusting the people that work for you and letting them do the work they need to do.

JEFF: Yeah. Absolutely. (57:46) Well, Josh, if anybody wanted to follow-up with more questions for you or find out more about Planetary, where should they get in touch with you?

JOSH: You could find us at planetary.co and if you want to get in touch with me directly, I’m on Twitter @endtwist.