Show Notes
Tyler: In this episode, we're gonna talk about the pros and cons of remote work, such as when does it make sense for a company to have employees altogether in an office versus fully remote or something in between.
Rick: I personally get this all of the time. I've heard of four core models that . One is “single site” which means everyone works in the same office environment. Second, is “multi-site” where you have multiple locations with everyone working within the office. And then the third is “satellite”, in which most of the team is together, but a few people are remote. In other words, it's more of a hybrid model. And then at the complete other end of the spectrum is “remote-first” meaning everyone works from a separate location by default and then comes together when necessary to meet in-person. Does that cover the gamut of options in your opinion?
Tyler: Yeah. It's kind of a sliding scale so everything in between is fair game. But, yeah. More and more, I think people work at a company with lots of people, but they work remotely or they work in coworking spaces or whatever. So the world is trying to figure out what makes sense for which companies here.
Rick: In my most recent consulting project, I'm working remotely. It's the first time I've actually worked remotely for a company before. So, that was an interesting experience. I'm interested in what your experiences are with this. Do you feel like there's a right way to do this?
“There's not a one-size-fits-all, right solution”
Tyler: 100 percent, no. There's not a one-size-fits-all, right solution. I see a lot of arguments in favor of remote, but my experience is that, in practice, doing remote has a lot of challenges that I think get glossed over when people talk about it. So, I think there's there's pros and cons to both. Philosophically, I want remote to be the answer. But, in practice, I haven't seen that to be true so far.
Rick: Before we go into pros and cons, tell me why you want remote to be the future.
“Talent is global… if you limit yourself to a specific location, you’re limiting the talent pool”
Tyler: Just to name a few people [and companies] who are advocates.
Basecamp is remote-first.
Doist is remote-first. If you follow the founders on Twitter, they talk about this a lot. I buy the argument that talent is global. It's spread out all over the place, and your company should be trying to hire the best people possible. And if you limit yourself to a specific location, you’re limiting the talent pool. The other [argument] is that we are all adults. There’s something that seems almost like an industrial-age assembly line about having everyone commute to the same place and sit in desks next to each other in order to get work done. The internet is a thing. It doesn't seem like we should need to be next to each other. So that's why I feel like it should work.
Rick: So one [argument] is that [remote-first] allows you to attract a better breadth of talent from different locations. More diversity and people that you would never even think of hiring at a co-located place. And then on the second argument, I understand that you don't like the industrial nine-to-five feel of an office. But, what is it that you would replace it with?
Tyler: Well I like the idea of if you get your work done, as the boss, it’s not my business how it happens. Historically, I feel like too many employers felt like they owned their employees. I mean historically they actually did and that was obviously terrible.
Rick: Are you talking about slavery?
Tyler: Yes. We haven't broken out of that fully, we're still, I think-- plutocrats exert way too much control over the people who work for them.
Rick: Wait, what's a plutocrat?
A plutocrat is a person whose power derives from their wealth.
Tyler: Rich people who run the world, basically.
Rick: Are you a plutocrat?
Tyler: I'm working on it. [laughs]
Rick: All right. Sorry. Keep going.
Tyler: Basically, like what you and I are doing right now. You're in Utah. I'm in Missouri. This is fine. We're both adults. We're getting this thing done. Should I have to fly to you every week in order to record a podcast? Of course not. Why does everyone have to drive to the same office to get work done?
Employees gain autonomy and flexibility from remote work
Rick: There's a lot of benefits [to co-location] that we'll go through later, but what I'm trying to get to is what is it that you gain from [remote-first] as an employee?
Tyler: I think it's autonomy. You get to decide where you live, you get to decide, "Do I want a standing desk? What kind of chair do I want?" You just have total control of your work environment.
Rick: Flexibility. Employee flexibility. Got it. Yes, it's the ultimate flexibility. Get the job done, work when you need to. I don't think that always applies. For some roles, you will need to be available whether you're remote or co-located at a certain time.
Tyler: Yes, there is time flexibility, but that's maybe orthogonal to environment flexibility.
Rick: You're killing me with these words. What's orthogonal?
In statistics, orthogonal means statistically independent
Tyler: Perpendicular. It's like an unrelated thing.
Rick: They cross over each other?
Tyler: Yes, it's just that they're pointing in different directions. These are two points. Your time flexibility is almost completely independent of your location flexibility. Support needs to be on at a certain time, they don't necessarily need to be in the office to do their job.
Rick: Location flexibility is really what you're arguing for here?
Tyler: Yes.
Rick: I like it. There's also work environment flexibility, which gives the employee choice on the desks and stuff. I get it. What's stopping us, in your opinion, from getting to where everyone's working remote?
“It's very, very lonely to work remotely”
Tyler: My company is not remote for the most part. We have a little bit of a hybrid model, but we’re mostly not remote. Obviously, despite my philosophical agreement with it, I think there are some real practical problems. I can just rattle off a few. One is, it's very, very lonely to work remotely, especially if that means you're working from home. Remote can also mean going to a co-working space and being around people, but those aren't the people you're working with, so I think there's still an opportunity for loneliness there. I don't know if you've ever done that type of thing.
Rick: I am a little bit different in this regard. I actually like to be by myself, so I can't relate to this. In fact, when I see people working at Starbucks or at a coffee shop, and they're just hammering away on a keyboard, super focused with headphones on. I don't get it. [laughs] It's the last place I would try to get work done.
Tyler: 100% agree. I did five years fully remote from my apartment, no coworkers at all. I loved it, but most people don't.
Rick: Yes, that's my experience. Even at my former company,
PeopleKeep, we had a flexible work-from-home policy, and I took advantage of that, especially early in the morning until about 10:00 AM where I could just get a ton of work done without being interrupted. I loved it. I’ve also loved my most recent consulting project. I'm doing a lot of work from home right now. I don't suffer from this loneliness that you're talking about.
Tyler: But people do. One of the biggest challenges is that it’s very hard to have that culture that's both remote and co-located (being in the same office). It's easy to do one or the other, but it's hard to have a hybrid of the two. I hear what you're saying, but if everyone's not like you, someone on the team may be feeling that loneliness, which is an issue. That's one issue. Another big one I have is I don't think that remote work is a very good fit for entry-level hires or any situation where you need mentorship. If someone knows how to do their job already, and it's just like, "Here's the work. Go do it," I think remote work is great. For someone who is either coming out of school or doing a career change, they're trying to learn new skills, and I feel like being near your mentor is just essential. Also, not everyone knows how to do remote work. It's just really throwing them into the deep end and saying, "You have to learn this new skill all by yourself in total isolation." My company is built around mentorship. We only hire entry-level people and build them up.
Remote-first makes it very difficult to hire and scale entry-level talent
Rick: Yes, I totally agree. When you have to teach someone how to be a professional worker (I'm using the professional word to mean a job that has certain expectations of it, just by the nature of being in the office: how to use email, phone etiquette, meeting etiquette, basic principles of working at a knowledge worker job), it's like teaching grammar, honestly. Yes, so I agree with that. Remote-first would prevent you from hiring entry-level people and scaling them like you have.
Tyler: I know Basecamp does this. They only hire people who are already at least somewhat experienced, and in most cases, they want to hire someone who's already worked remotely before.
Rick: Yes. What else? Loneliness is one downside. The inability to make entry-level talent work is another one. What's another one?
Tyler: I think I've got two more. My next one would probably be, this is related to loneliness, but culture. When we started,
Less Annoying CRM was fully remote, to begin with. My brother, who's my co-founder, was in Boston. I was in San Francisco. That's remote. When we started hiring people, we didn't have an office. So they were remote. Eventually, the team said they wanted an office, which I found shocking. I was like, "This is this amazing benefit. You can work from wherever." Some people like it, but a lot of people wanted an office. Your coworkers, especially as you get older, they end up being your friends, in many cases. It's harder to do that if everyone's in different places.
“Your coworkers, especially as you get older, they end up being your friends”
Rick: This third one feels like another loneliness type thing.
Tyler: It's like loneliness, but I guess loneliness is more personal. I should phrase this as it's from the company standpoint of the company needs a culture, and it's much easier to maintain certain types of cultures in person.
“In-person interactions are what helps develop culture, and you miss out on that with remote”
Rick: Got it. In other words, in-person interactions are what helps develop culture, and you miss out on that with remote. Although, I would say that working remote if you have a sequence of getting together, in person, to supplement that, you could probably make that work.
Tyler: Yes. I don't want to suggest that companies that are remote don't have culture. I think it's just a lot more challenging. Human civilization, for centuries, has been based on in-person interactions. I don't think we fully understand how to create certain types of cultures without face to face interaction.
Rick: Yes, it may not be possible. There's a lot of communication that happens that we don't understand, just based on body language and tone and that sort of thing. Who knows what's being missed out on when you're not in person?
Tyler: I know companies that do fully remote. They have an annual in-person meetup, and some do quarterly. There are things you can do like Zoom meetings and coffee breaks over Slack, where everyone will have coffee at the same time. But it's not a replacement [for co-location]. Today, 24 people at my company sat down and ate lunch together. Every Thursday we do this. It's just you can't replace that online.
Rick: Yes, breaking bread is powerful.
Tyler: I've got one more, but what are your pros and cons here?
“There's just so much clarification of what is important at the company, what needs to get done, who's doing what. All these things that you miss out on when you're remote”
Rick: For me, it all comes down to communication. One of the hardest things in a team whether you're in the office or not, is that communication is so hard. It helps so much when people are rubbing shoulders, talking at the water cooler, and talking about priorities of the company and helping to clarify them across the organization. We found it very difficult to replace this when we had remote employees that were full-time remote. We tried all kinds of things. We had video hangouts going all the time in certain parts of the office so they felt part of the team. But, it’s not the same. There's just so much clarification of what is important at the company, what needs to get done, who's doing what. All these things that you miss out on when you're remote.
Tyler: When you and I talk outside of this podcast, one topic that comes up a lot is trust. The best professional relationships are built on trust and it's really hard to build that. An example of this, you might say to someone you've never met in person "Hey, can you do this?" Then they say "Sure." Will they be upset that you asked them that? Who knows? If that happens between you and me, I think you know me well enough that if I was upset I would say something to you.
Rick: Yes and we've spent a lot of time together in person.I'm sure that people have figured out how to do this remotely. Certainly, that is the big scary thing for me about this. I've got my partner for
GroupCurrent up Park City, Utah. I'm in downtown Salt Lake City right now. We don't have an office, and I actually like that because we're virtual and it's obviously no overhead. We try to meet in person at least once a week to continue to build our relationship. It's a pretty productive meeting now, but when we were doing this early on in our relationship there was definitely a lot more miscommunications. We actually stopped doing remote meetings and came together until we built a sufficient amount of trust. Now we're coming back to those meetings and getting a lot more done. I don't know if that was just time or if there was an important in-person element that we needed to create first in order to develop that trust.
Tyler: Yes, that mirrors somewhat like Less Annoying CRM, once again my founder is my brother. We have met in person before, so it's really no problem at all. And then we hired a good friend of mine who lived in the same city as me so I could see him face to face. Eventually, we started having more and more people who aren't like that and that's when the moment hit us like "Okay now we need to go co-locate." Yes, I think that lines up with what you're saying.
Rick: I don't know the answer to this. I really like the idea of remote, but I just can't imagine doing only remote. So for me,it would really have to be remote-first. I like the remote-first term. There is some very important in-person stuff that is mandatory in order to make remote-first work. I don't know what the frequency of that is but I know that when a new person comes to the team, that frequency would be much higher than someone who's been on the team for a longer period of time.
Tyler: I think it's very common with remote-first companies to say: “When you join the company, you're going to spend a week or a month in a location with at least one other person on your team.” I also know there are those who are remote, but they want to hire people in clusters in the same city. There might be people in five different cities, but each city has at least two people, and they meet up once a week or something like that. There are different ways to handle that, I think. I've done fully remote, very, very small. I think we were fully remote at six people, and then we co-located. I've done it. I don't think it was that bad. I think it's possible. You have to be really deliberate about it.
“It was shockingly difficult to have a hybrid approach because, to do remote well, culture has to be fully online.”
Tyler: The thing that I found surprisingly difficult is when we decided to co-locate, we grandfathered all existing employees in, and we just had all new employees. I was in San Francisco, moved to St. Louis, and said, "This is the office. All new employees need to be in St. Louis." It seemed pretty messed up to force everyone to move, but it was shockingly difficult to have a hybrid approach because, to do remote well, culture has to be fully online. Every conversation has to be in Slack. Everything has to be online. To get any benefit out of co-locating, the whole point is that stuff's happening offline. Balancing those two things is super difficult. Now, only one of the remote people is still with the company, and that's my brother.
Rick: Is it because you can't fire your brother or is that because he makes it work?
Tyler: It's a combination of things. One, is personality. The other people needed more social activity. Two, I have very good lines of communication with him, and three, he makes it work. He's more like, "I've got a family. I love the lifestyle that remote brings, and I'm okay if that means I'm not at all the company events and stuff like that." The other people who were remote, that wasn't the case. They had other job opportunities. One was in San Francisco. He had previously worked at Facebook. He was used to a very, very, involved culture. He was like, "I don't want to work remotely when I could go actually have lots of valuable social interactions with my coworkers.
Rick: Every single night, if I want to.
Tyler: Yes, exactly.
Rick: That's interesting. Is your brother an individual contributor or does he have director reports?
Tyler: That's a great point. We just hired the first person that reports to him, although, we're co-managing that person. He's the technical lead, and I'm more of the people manager. Basically, no, he is definitely an individual contributor.
Rick: It makes sense. I think that that works. I had a very similar problem with the hybrid approach because some people just aren't thoughtful of the remote employee in certain cases. For example, every company meeting, guess what needs to happen?
Tyler: Video chat.
Rick: Video chat. Some people, if they got there early, just wouldn't think of the remote employee. I couldn't get everyone to share the importance of inclusion of people who are remote and going out of the way for communication. Communication was hard enough just with the people internally, that getting them to go out of their way to support the remote people, it would just mind-boggling to them.
“Communication was hard enough just with the people internally, that getting them to go out of their way to support the remote people, it would just mind-boggling to them.”
Tyler: I'm interested in whether or not this solution worked for you. You said you are pretty open to anyone, even if they came into the office, they could work remotely if they needed to. We have something like this. We have basically one day a week and two weeks a year, anybody can work remotely, but most of the time they're in the office. What that means is everybody has experienced being the remote person in a meeting. Did this happen for you or did people just not work remotely enough for them to have that experience?
Rick: It was a subset. Oftentimes, people would work from home around a vacation. Let's say that they had a flight that evening, but they didn't want to come to the office and waste time and commute, they could work from home that day. A lot of times, they'll work from home. It wasn't, "Hey, I just want to work from home today." It was built around convenience for time off or a personal matter that needed to be attended to. We didn't have any policies around how many days or anything like that, but yes, I don't know why. It wasn't easy. That's all I can say. A lot of people were entry-level. Coming back to the entry-level talent, there were several people who took advantage of this, we're remote, and didn't understand the importance of cascading communication. The communication from the top or the bottom only works its way through the organization to the right people if people cascade communication. I'm starting to realize it comes all the way back to entry-level people. One thing that most entry-level people don't get is the importance of over-communication, both upward, sideways, and down if you have people beneath you. I realize now that that was the key element that was missing.
Tyler: I think that could maybe be generalized to say, "This is culture." Normally when you say culture, it's, "Do you shoot Nerf guns at each other and play ping pong?" But how a company communicates is part of culture. If you're fully co-located, you can be a little sloppy with it because everyone already knows how to do that. If you're going to go remote, either partial or fully remote, probably you have to be a lot more deliberate about this, like how does communication work here? And you need to say it out loud to people probably.
“If you want to have entry-level people, [remote-work] does not work.”
Rick: Yes. We tried that. For us, we had a majority of entry-level people, meaning this is either their first job or second job out of college. They're more worried about how to schedule a meeting, all the basics, right? In looking back, the more experienced people were the ones who would go out of their way to get remote people involved, and they were thoughtful. I'm really coming back to entry-level. If you want to have entry-level people, [remote work] does not work.
Tyler: If it does, I have yet to see it. I think 10 years from now, someone will have figured this out. It's notable that the famous, bootstrapped software companies that are remote tend to hire a lot of entry-level talent. It's not a coincidence.
“One takeaway is to make sure you're clear on what types of people you need to operate your business before you decide to be remote-first or single-site or somewhere in between.”
Rick: I want to unpack something. One takeaway is to make sure you're clear on what types of people you need to operate your business before you decide to be remote-first or single-site or somewhere in between. But, does the business drive the talent in this case or is there a decision that can be made by a business upfront that says, "Listen, one constraint I'm going to place on my business is we're going to be remote-first, and we're going to figure out how to operate this business that way." It feels like you could go either way.
Tyler: Yes. I think it could go either way.
Rick: Yes. One is, "Hey, we're not going to do any business that won't work with remote," which means we've got to hire experienced people. That constrains what business opportunities we can go after. I go the other way though. I feel like this is not the right reason to start a business. The right way to do this is to start with what problem do I want to solve?
Tyler: Yes, you run into this with other things, too. Like my big thing that I mentioned in every single episode is bootstrapping. This is one where it could go either way, you could say, this is the problem I want to solve. Is this one that should be bootstrapped? Or should I raise money, but I went the other way. It's most important to me that I don't have any investors. I only consider business models that would fit that, to me being remote is not that level of important, but to some people, it might be.
Rick: Is it for entrepreneurs? I would say that if you've been by yourself at home is of importance to you at the start your business, and you want to grow it to multiple people. I don't really-- It doesn't add up to me.
Tyler: It shouldn't. I agree, probably if you're doing that, at that point, it's more of a lifestyle business, which is fine. I don't mean that pejoratively, but the only reason that should matter is if you care more about your lifestyle than anything else.
Rick: What do the Basecamp people say about this issue? Was it an early decision driven by lifestyle? Or was it driven by the talent they needed?
Tyler: I'm not sure I've heard anyone frame it like this: “Did you derive this from the business needs? Or did you derive the business needs from the desire to be remote?” The impression I get is everyone rationalized it after the fact. I don't think anyone planned that necessarily. I don't know. What you said is very interesting, because I can see this playing out with what we did. Because when we started, I thought we were going to be hiring experienced people, a small team of really good people. I had no interest at the time of hiring entry-level people. For example, almost all of our Dev-team didn't know how to code, we taught them how to code. That is not something I ever thought we would be doing. To be honest, CRM software doesn't demand really technical, like senior engineers. You don't need someone who solved incredibly difficult scaling challenges at Facebook to build a CRM, it's just not a requirement. So yes, I think exactly what you're saying is what happened. We didn't plan it this way but the business needs demanded entry-level people. That's probably why, after we started, we switched away from a remote model.
Rick: Yes, it feels to me that probably the business needs are what is going to drive things. Otherwise, you end up shutting the business down. If you aren't comfortable operating a business, the way it needs to be operated to succeed, you pivot.
Tyler: But you can intentionally say I'm going to start a company that fits remote model. Like I could have done that. If we'd had this conversation 10 years ago, I could have made that a constraint.
Rick: I'm very interested in finding someone who has decided that for that reason. Supporting the remote model and being remote-first are two different things, by the way.
Tyler: Absolutely, well, how about you? You are at a point, you previously were the CEO of a mostly co-located but not entirely bigger company than Less Annoying CRM is. Now, you're starting up various new things. Presumably, at some point, you will, again, have employees and whatever. How are you going to view the remote question when the time comes?
Rick: For me, the biggest pro I see about remote work is being able to get stuff done uninterrupted when you want to get stuff done. The second is the talent piece being able to acquire the best people. Like, if I could work with you again, at some point in time, I would not let co-location get in the way of that. That's just stupid to me. But we have a lot of trust.
Tyler: How many people have you already worked together for years with though? There's a small set of people.
Rick: Sure. Yes, but there's people out there who are so worth the ability to hire and work with that co-location simply shouldn't get in the way in my opinion. I can't imagine not having a pretty solid come together strategy. Once you get to a certain number of people, where there's regular, weekly, for the most part of for 99% of people coming together in person. I can't imagine that.
Tyler: Remote, but not distributed, sort of like you work from home, but you're in the same city as everyone else.
Rick: Or you're flying them.
Tyler: Every week?
Rick: Yes, that's where I'm getting. I don't know what the frequency is, but it gets really hard. I don't know the answer. Maybe it's two weeks.
Tyler: You save some money not having an office but not enough. Even a once-a-quarter big company retreat, I don't think you can afford with the savings for an office.
Rick: For me, being able to have flexibility with work is important. I want people to be able to get the job done and not feel like policies around when you're in the office in person getting in the way of that. I'm very much a flexible, outcome based, get the job done. Remote would never be a reason to start something for me, but I definitely want to build a company that enables people to be measured on getting a job done based on, not hours worked, but what was delivered. I don't think that works on a fully remote basis. Man, that would scare me.
“It's hard to lay down roots in a city if your employees are remote”
Tyler: It can, but it doesn't for every business. What you just said made me think of something that I hadn't considered. When we started Less Annoying CRM, the goal was to build software. Nothing too grandiose. When we moved from San Francisco to St. Louis, St. Louis really embraced us. This is my hometown also. We had started feeling a certain responsibility to the community and that's another thing that's really hard. It's hard to lay down roots in a city if your employees are remote.
Rick: You're hitting the thing that I'm trying to express. When you say "culture" it doesn't resonate with me, but when you say "community", it does. I think that's the scary thing for remote with me: “How do you build a community of employees that is part of a larger community of, whatever, trying to get stuff done that matters and sharing in that?” That solves the loneliness problem. It's a big part of why work matters to people. Community, I think, you have to have that to be a successful company whether you're remote or not.
Tyler: See, Basecamp disagrees.
Rick: They have community. They have one of the most notorious, annoyingly brash communities in the past 10 years.
Tyler: They do, for their customers, sure.
Rick: No. I'm talking about them.
Tyler: But, if you listen to their founders interviewed or anything like that, they say, "It's none of our business who you are, where you are. We're professionals, we work together, and then you go have your friends." They would not say they're trying to build a community among their employees. I'm pretty sure.
Rick: They are the most opinionated. They've written books about how they think work should do. They're very contrarian and that is the basis for a community. Only certain people are allowed to work with them. Maybe their community is around what you just said. "Hey, we stop work and we go hang out with our families and we don't do more than that." There's a community there that's forming around that belief.
Tyler: Okay. I would use the word culture. You'd use the word community, but okay. I hear what you're saying.
Rick: Absolutely. Culture is a scary word. [laughs]
Tyler: [laughs] All right, well we can unpack that some other time, I guess.
Rick: Cool.
Tyler: Cool. All right, great talk.