could hiring asynchronously create a team of robots w/ Brian Casel, CEO @ Zipmessage

The hiring process currently depends a lot on team & culture fit. Will hiring asynchronously create a team of bots that have little interaction? Potentially killing culture and the idea of teams.



1/3/202243 min read

Here's the recap...In today's episode, I chatted with serial entrepreneur Brian Casel, CEO of ZipMessage. We took a deep dive into asynchronous communications. Focusing on a new trend of asynchronous hiring. We spoke about the benefits of asynchronous be default remote cultures. Helping employees flip the switch from living to work to working to live. However, we noted the slippery slope async may lead to. Without synchronous team engagement, it could break company culture. So how does hiring someone without ever speaking with them live help the company ensure culture & team fit? If you're expanding your remote team this year and interested in how hiring synchronously vs asynchronously may affect the quality of hires, listen in...

Brian on Linkedin

Brian on Twitter


Bootstrapped Web

black wooden table with chairs
black wooden table with chairs

Yep, you should still speak with a candidate synchronously

Brian has hired quite a few people over the years mostly asynchronously. Now he's dogfooding his product ZipMessage to interview and collaborate asynchronously with applicants. Asking questions, clarifying deliverables, etc thru short videos. Yet, Brian still starts off this process with a short 10-15 minute Zoom call. Just to get to know the person a bit from the start. Using the age-old method of knowing whether you'd like to partner, invest, date, or similar within the first few minutes.

Live conversation also introduces new constraints and ways of seeing the employee. With async video, the candidate has the opportunity to retake the video and craft it to be nominated for an Academy Award for video shorts. It's important to put someone on the spot, make them have to come up with something, or just hear their first uncrafted thought.

Will hiring asynchronously kill the concept of teams?

I'm personally not bullish on the idea of hiring asynchronously. Well fully asynchronously. There are definitely bits and pieces through the hiring process that are perfect for this. I've personally always hired for culture/team fit. Is this person, someone I'd invite over for a beer & BBQ? Is this someone I'd be excited to work with? These are a few questions I'd ask myself during the interview process. I believe this is crucial for an early-stage startup where every hire counts. Hiring the wrong person will kill your company. So if you can't get it wrong, it's important you get it right. How that person would succeed with the team and how the team would further succeed with them is priority 1 for me when hiring.

If hiring everyone async, that builds a culture where no one ever speaks to each other. Without synchronous engagement and collaboration, how do you build that sense of team? How do you create that feeling of being on a shared mission together? If never speaking with teammates, you're just there to do a job and go home. That builds a lack of care for the global good and success of the team versus only your success. In essence, we'll all become robots that 'automate' the job without input or interaction with the other robots.

Async hiring can be great for test projects

Where async hiring can thrive is in the idea of test projects. At InVision we used this method at the beginning for hiring developers. It's an opportunity to focus on the output of the candidate versus the candidate themselves. So throw up a job post, select the top 10-15 candidates based on skills required to complete the task. Do the 10-15 minute synchronous zoom just for that get to know you. It's likely a few of the candidates will not get past this round. Then give them a paid task that runs over a few days or a week. Invite them to a Slack account or build in those opportunities to communicate and collaborate asynchronously. You can provide them with a video overview of the project and expectations. They reply with clarifying questions via audio/video/text. You resolve those open questions. Etc.

Now, perhaps the top 3 or top 5 candidates (if applicable) move on towards a set of longer synchronous calls. Where you now dig in to understand if they'd be a good culture/team fit. Perhaps another of them presenting their project and answering questions.

[Scott] Brian, thank you for joining me today.

[Brian] Going good. Hey Scott. Thanks for having me on this is, this is going to be good.

it's an absolute pleasure as I spoke to you offline, I've been listening to your podcast for over a year and, and a big fan. So it's certainly an honor for me to be able to get to, on our fair with, especially as you've been moving towards remote work and, and Eastern, the communication will be interesting to hear what you have to say about that. Yeah. Where are you, where are you calling from these needs?

I live in Connecticut. my wife and two kids. We're, we're on like the, like an hour north of New York city over here. so it was fun to meet people who, who have, listened to our podcast for only about a year. Cause we we've been doing it for like, I don't know, seven or eight years now. And, I like, I people sometimes say like they start from episode one and I just hope that they don't, I, I, I only want people to hear the more recent stuff, you know?

Yeah, yeah, yeah. It's good. The consistency now that's always the biggest thing. It's a no, are you consistently enough and putting that out there, especially with changes and starting new companies or selling other companies or whatever else is going on in life, whether you continue in pushing that consistency. And, yeah.

[Scott] So I think before we jump into the topic today, wanted to throw something out there that was a news the past week, with, the country of Portugal passing some hopefully remote friendly laws around the idea of not bosses, not being able to message you after hours, some kind of requirements to allow you to work remotely. I don't know if you've, if you saw the news, if you did, any thoughts on positive changes, negative changes, So forth.

[Brian] Well, I haven't seen that news. That's that's pretty interesting. So, so is it that they actually have laws like against message, like sending messages communications after a certain hour,


[Scott] Correct. Yeah. Well I think trying to help. Yeah, really trying to help with that work-life balance and ensuring that you don't get those slack messages after you're done with the day. So it's definitely nice to see.

[Brian] I haven't really seen the news story about that, but, not to get too political here or anything, but I, I do question cause I, I completely agree with the notion of that sort of guideline. Right. but I feel like it should be more of a guideline than a law because I think that different companies operate at different times and people, individual people there, there are night owls, there are morning people, you know, some people like to do some of their work at different hours. but I, I like the, like in tech, in some of the tools, like the way that slack has, you could send a message at like midnight if you want to, but it won't bother someone until their next morning, you know, like that kind of stuff is good.

[Scott] Yeah. I think it's probably a lot focused on that of if you're working a typical nine to five that you're not getting slack messages, no seventh 30 is saying, Hey, you know, what's the update on that? Or what, what is it, you know, the answer on this. but as you said, I'm assuming that I haven't dug into law. It probably isn't looking at those cases where, yeah, you're a night owl, you enjoy working at night. So you're going to either reply to messages at night or they'll send new ones, which then I think, again, it's the expectation. and that's big part of the idea of synchronous versus asynchronous, which I know we're going to get into. It's an expectation, right? When you get the message, like in the old days and email, right, you got an email at seven 30, was your boss expecting an email to come back, you know, within two to three minutes or no, as we move forward, it's just, okay. I sent you that email whether I should or shouldn't have at that time. But what is that expectation I might expecting?

Is there any expectation company-wide that I'm going to get a response within a certain amount of time or we're not,

You know, I'm sure that we'll get into this, but, that's actually, I think the key word there is expectation and, and I think that there, there should be, you know, because I, I hire, I've been hiring people remotely for over a decade and yeah, the, the best people to work with, go above and beyond to set expectations about how the, how, how we should be communicating. And so like what I really cause I really like to move quickly and I do like to, you know, I just, I'm impatient. I don't like to wait around for things, but, but I, but I also really believe in not rushing people to do the actual work. So I think that in terms of communication, it's really important to, not expect them to like do the work within an hour or, or same day, if, if, if it's a thing that actually requires like a full week or something, but it is really important to, to reply, I think within a business day to say like, Hey, yeah, got that request. Or, yeah, I'll be working on this on Thursday. I should have this to you by Friday. Or like, just, just let me know so that I'm not wondering, like, what am I going to hear back from the person know?

[Scott] Yeah. I mean, I think as you said, it perfectly, it's setting that expectation. We had a mirror from newest last year on the show is the king of asynchronous and interesting. Now, as he's building out twist, who is specifically speaking about how they wanted to remove the Brian is typing Scottish typing or the re read receipts type things that you have in WhatsApp of getting away from that. Okay. If send a message down, I'm looking, is Ryan looking at it? Is he typing his typing response versus creating that expectation? I'm sending this and okay. Whenever I get a response, I get a response. but yes, I think it's a lot of it's building that expectation. I, as the Senator, I'm sending it, I don't have the specific expectation of when you're going to get respond to it. But I do value that point of on the recipient side of at least just saying, yes, I've got it. Here's what I'm going to do. And just, again, setting that expectation back of, I shouldn't have an update by end of day, you'll have it next week or whatever. Yeah.

[Brian] Yeah. And I think, I think people who are, who are accustomed to working with a team remotely, you know, I know the whole world is sort of new to this now, but a lot of folks in our industry have been doing it for many years. And so what I, what I think the great remote teams really start to understand is that you actually do have to communicate more than you would if you're in an office together, you know, because some simple things like, like, Hey, can you, can you take care of this task for me? If you're in an office together, you know, you'll hear someone say like, yep, I'm on that or whatever. Right. Yeah. but if you're across the world, I'm getting a notice here.

So I'm Brian Casel. My company and product is called zip message. That And that is a tool for, asynchronous, obviously the theme of, of today, right? asynchronous communication, really conversations on video. So it's a way to send anybody a link and you can hop right into, a video based, back and forth. Well, you can record video, you can record just audio, you can type in text if you want share your screen. and, and it's asynchronous, so you can just send messages back and forth. and, you can, you know, the nice thing about it is that you can have like private within your team, or you can just send a link off to anybody like a customer or a client or a freelancer or somebody that you're hiring and, and, and, you know, get the, get the communication, really get the conversation, move it forward.

Awesome. so where did it come from? I mean, I I've been, working remotely and, and self-employed for 13, 14 years now. basically that entire time I've, I've been remote before that I worked in an office, you know, as a, as a web designer originally. over the years, I've, I've kind of grown my skillset to be more of a full stack software designer, developer. but I'm really more on the design side. and, for first I've had several businesses over the years, a couple of them that I've, built up and sold and built up remote teams. And, and, one just recently I sold like two months ago, that was called audience ops. And, and so now I'm focusing, thank you, you know, focusing everything on, on zip masters now.

[Scott] Amazing. so I think that the way that I reached out and the conversation starter was you had tweeted a message about hiring asynchronously. So we'd love to know, obviously is you've been working remotely for awhile. but async is really kind of come to the forefront the last six to 12 months. How did you decide to start hiring asynchronously versus synchronously? And how's it going so far?

[Brian] Yeah, that's a, that's a really great question. I I've been hiring people remotely from, from across, from everywhere, all over the world for many years. And usually the way that it would happen is I would put up a job posting. I would receive back, applications, usually through a form that I put up somewhere. yeah. And then, and then I would pick a few, people that I want to interview, and then I would have a live zoom call and usually pretty brief, like 10, 15 minutes talk to a person. and then after that, so I'd probably do like five to 10 of those interviews, first interviews. And then I might, depending on the type of role it is, I might do a second interview, or I might just go ahead and start working with someone, but what I, what I learned more recently in using zip message for this is, number one, the, the front end, like the, if you think about hiring like a funnel, that the, the people who come into the top of the funnel, the people who submit their applications in, in certain types of roles, like in marketing, or if it's somebody who's going to be on like podcasting with you or doing that sort of stuff.

but even, even like more internal stuff like developers, it's, it's good to see, like face-to-face how somebody communicates. Right. Sure. so number one is that Zipmessage, allows me to receive applications on video. They can, they can still send their resume in and answer some questions in a form, but they can send me a minute or two video, either show me their screen or show me their camera. it's been really helpful to see a wide number of, of applicants and they can actually show me their screen and show me something recently that they, that they worked on recently, that that number one gives me a much higher level, evaluation of like, who are the best candidates in here because some people are really great at filling out forms. Sure. Or they're not so great at filling out a form, but they actually do really amazing work.

And if they can show that to me, without me having to interview a hundred people, just to find those, those gems, that that's number one, but then number two, I think this is even more important is after, I've had the initial, like meet and greet or, or an initial message back and forth, before I'm actually ready to kind of, you know, actually make the job offer and start working with a person there's still a lot more that I want to like hash out with maybe the top one or two candidates. and instead of having to schedule a second zoom call and a third interview, a third zoom call and, and all this stuff, I'd, I'd much rather do that asynchronously. And so I've been having, like, it would extend for like a week or two, we would go back and forth maybe eight to 10 times, you know, a question about this here, let's talk about the pay structure.

Let's talk about the schedule. Let's talk about some of the, the first initiatives that we want to work on together. Just, you know, batting, initial thoughts around on these before really feeling comfortable, like, okay, let's, let's go ahead and, and start actually working together. that has been really, really helpful. I mean, literally just this week, I brought on a, a new marketing person to work with me. I'm in Connecticut, in the United States, he's in Australia. normally that would, that, that times, that difference between Australia and us is like single worst mismatch in around the world. but we've been able to have like really deep dive, really quality, productive conversations because you know, we're doing it all asynchronously. So, and, and it's on video. It's not just slack or emails, you know? Yeah.

[Scott] It's interesting to kind of know where you're ending off here, because I was thinking the reason potentially you have those intro 10, 15 minute calls and you have multiple calls it's because at least my experience, you're getting to know the person now is this the right person for me? Is it the right fit culture fit? We're going to go into it a little bit later. but that was really the point of having these conversations. Yes. Do they communicate well in person?

[Brian] And that's still important. And I still do that. Like, I, I still do have a live zoom call, like a brief okay. Call, you know, after I received their initial application, which might be a video application from zipmessage, then, then I'll, I'll pick the top few and then I'll do, like a 10 minute lives, zoom call, just, just a meet and greet, like, just to see, like personally, what are they all about? You know? cause I like, we can't really hash out the full, deep dive of the role in a 10, 15 minutes zoom calls. So it's just to meet and if that goes, well, then we'll do like a week or two over asynchronous, you know?

[Scott] Okay. So maybe there's no mind diving into the actual process a little more or less. You said you started off with getting in applications for the kind of tough, people come in and you'll do a short 10, 15 minute synchronous call over zoom or similar tool that those people who passed that. And now you move to that two, two week, no back and forth asynchronous. is it more focused on again, conversation, cultural fit personality, or you started diving into actual work? or kind of, again, I don't know if you do a lot of companies now do homework assignments or take-home assignments or things like that. Is it like a mix of that of explaining or going through, what does the process actually look like?

[Brian] it very much depends on the role that I'm hiring for sure. but most recently I hired a person to help with marketing, mostly like content creation, kind of kind of work. and so, that looked like again, just a meet and greet on, on zoom. and then, an asynchronous back and forth over about two weeks using zip message, that conversation that the async part was mostly, dealing with. the, the fir first it was, it was about like, let me get to know this person and their background, like show me their, like he showed me, similar projects and engagements that he's done in the past and why, why that makes him a good fit for what I'm looking for. And then we moved on to, okay, these are the big initiatives, the big projects that we're going to work on together.

And I started to kind of hash out like, we didn't actually start working on them themselves, but we talked about like, these here's what the goals of this would be. here's the general idea of, of creative direction of where we want to go with this and then I want to get his thoughts. And like, where would you start with this sort of thing? What are your like initial, like off the bat, some ideas, again, not going deep on the actual work, but just let me hear how you would think about this type of project. And then the, and then as we neared the end of that process in the async conversation, we started to talk about structure like, okay, here's, here's the pay structure? I think we could start with, a project with, a dollar amount and here's what we want to do.

And this first project will take about two months and then if that goes well, and that's not a test project, that's actually starting the work that we need to do, but, but it's like the first two months. And then after that, you know, we'll probably roll into, an ongoing retainer and here's what the pay structure and scope for that would look like. And I got his thoughts on that and, and, you know, again, just setting each other's expectations about, about how all that is shaping up. And then if we're, we're both good with it, then, then from there, we, we, we actually started working together so interesting, in terms of like test projects, I've done those a few times. Like if I'm hiring a developer for the very first time, a software developer, I might do a small, you know, build, build this project as a test and I would pay for that.

And in my previous company, we, we hired right. That was like a content writing service. and so usually the writer hiring process involved having the writer write a full article for us as a test. but we, we paid them for that. And it was actually a real article that we would use on our own blog. and, yeah, but, in other cases I don't really do like a small test. It's really just more like, let's just actually start working together for like a month or two, and then we'll, we'll see where we're at after that.

[Scott] I love it. outside of obviously your tool, that's, an asynchronous, video tool. I know we had a couple of conversations on the, on the season last year around async and really got out of it that in theory, or potentially the heart of async will be long form writing. but there's obviously the value of audio and video and asynchronously. So within that interview process, do you include other forms? No formats of video, audio, audio, and long form writing, or is it mostly just focused on kind of the back and forth within the tool?

[Brian] For sure. There's definitely a writing or typing, as part of it, I mean, is it message you can, send video or audio messages, but you can also type in messages and also attach typed messages to your video. Like, it's very common that you record a video and then you, you talked about a few links, so you'll drop those links in the text right below it. also, you know, sometimes you just watch a video and then you just, you only need to kind of reply with a sentence or two, you don't actually need to record without, so you could send them a text, back and forth. So, so yeah, definitely in my hiring process, written communication is really, really important. So, the initial, application has, has like a text component that asynchronous back and forth where a lot of that is, is text as well. So, yeah, I mean, if they can't write or if there's grammar errors everywhere, like it doesn't obviously it doesn't need to be perfect, but you need to, you need to be, I call it like, like fluent in communication and communicating over the internet, you know, being able to Type quickly and then, and having like, don't give me like a, a huge wall of texts actually separate your paragraphs and make it easier for me to, to scan, you know, things like that. For sure.

[Scott] so you're speaking about how you're building theory your early, company in the early team. Yes. Drinker sleep. Do you feel that you could scale this and hire your entire future company a circumstance, or does it get to a certain point or maybe certain roles maybe as you look to get maybe executives or more senior level people that's where maybe more, synchronous, meetings and conversations would take place or do you feel, Hey, it doesn't matter what level, what role for the future of the company we could definitely hire and scale the company's synchronously?

[Brian] I really believe that it's a mix. Like I think each individual, hiring process should involve, a small amount of, of live synchronous conversations. Again, just to sort of personally, like get, get a feel for the person meet like a meet and greet type of call. and, but then I actually find that most of the deep dive hashing out of the role is actually better asynchronous. maybe like a higher level, you know, executive level, you know, it might make sense to have a few more live calls in the mix there, and maybe even an extended asynchronous conversation. but the big idea that I really like to get across, and, and this is any, asynchronous conversation, not just in the hiring context, but also in working together. You know, I actually believe that async is not just more convenient Siri to something I said, just triggered Siri anyway.

I actually believe that, async is not just, more convenient. It's actually a better conversation and you get higher, higher quality, more productive, ideas flowing back and forth. And the reason for that is if you think, if, think about when you're on a live call with someone you're, you're basically put on the spot, like you have to, somebody asks you a question that you don't want to have awkward silence. So you're going to respond with the very first thing that pops into your mind. And, you know, I'm sure many times that's going to be smart and correct, and accurate and helpful, but it isn't going to be your absolute best response to that question. Maybe, maybe not. I mean, if you're asynchronous, you can receive the question, you can process it, you can digest it. You can take a break for a few hours. You can come back tomorrow morning, you can do think about it. Then you can prepare your response. think about where you're going to say, maybe jot some notes down, maybe record at once. Hey, I could, I could say that a little bit tighter. Let me rerecord that before I send it off, you know, so you're going to send off a much better, well-formed like more creative idea. And, and when that happens back and forth, 20 times, the conversation just really exponentially increased in quality and, and productiveness, you know?

[Scott] Yeah. I couldn't agree more, I think that you can, and I think it really helps in hiring as well as, just working together, you know?

Yeah. I think the one word that comes to my mind with this is thoughtfulness. The asynchronous really gives me the opportunity to be thoughtful. When someone's asking me a question, asking for feedback, it's not that pinging back and forth about this. And then thinking thing it's like, as you said, I can think about it. I can write it down. I can edit it. I can come back the next day I could scrap the whole thing. I had some ideas in bed last night. I can come back. It's that real opportunity for thoughtfulness. It's totally giving the best quality feedback and thought process that I can in a complete manner. So again, it's not chunks here, chunks there. I got to now go through a slack thread of, no 50 back and forth and tried to put the pieces together. It's one kind of complete thought that covers all the bases, covered all the ideas and thoughts they have and keeping the conversation for that method and that slow. I think I totally agreement that. That's certainly where the future is going. And I think it's certainly, it's a much better way of communicating than just a slack ping, a ping pong back and forth.

[Brian] Totally. Yeah. And I mean, and like right now I'm, probably right by the time this comes out, we're launching a new website for zip message and I've been writing a lot about this type of thing, you know? yeah. And, and I really like to write about, and talk about the idea that like, it's you get the best that somebody else has to offer. It's not just the first thing that they have to operate. It's the best, like the best of, of, of their ideas, you know? and, cause you think about all the times when like, oh, I was on a meeting yesterday, I should have said this. And I forgot to mention that idea. Or I didn't say that as, as well as I could have, you know,

[Scott] Completely agree. a couple of questions that have came out of a podcast. I was listening to me about two, three weeks ago with, the CEO of Gumroad and it was not related to async, but it kind of moved in that direction and he was discussing how he hires now asynchronously. And that kind of piqued my interest. And I saw your tweet afterwards and he was really going into detail how you really tries to avoid synchronous conversations, gives the opportunity if that person in the interview process, once a natural synchronous call, if he's willing to do it, but it's very much focused of, if you can keep this asynchronous a hundred percent, then that's, that's the method to do it. And I personally had a lot of problems around that idea. And the first thing it's again, I think we touched on it earlier.

Maybe just my experience over the years, it's there was 10 to 15 minute initial calls me of the way I've hired. It's always really been looking for that personality. The traits does this person know mesh well with the team kind of culture. If companies and teams and leaders start moving more into complete asynchronous hiring, what happens in that scenario when you never really get to speak with that person before hiring them due to lose out, you would run into the opportunity of, Hey, this person looks great on paper or, or, or a short video, but when you actually get them on a team and now interacting with them, it's a totally different story.

[Scott] Yeah. A hundred percent agree. I, again, I think that there's as someone who is, I live and breathe asynchronous all day, I, I, I'm very anti meeting. I don't like having a lot of stuff on my calendar. I do strongly believe that it's important to have, to have, you know, live interaction. I mean that, that's where the occasional zoom call really helps for. Especially if you're meeting someone new, like a new hire, as, as we're coming out of the pandemic, I would love my team to fly to a city and get together for, for like a team retreat and actually have fun together. I think that's really important, you know? not like, and that's not for the purpose of working together. That's like, let's have a fun experience together in person so that the rest of the year we can work even better together, asynchronously, you know? so that's something that I'm really excited about. And, and you know, I think in general, this goes for just about anything I've, I, I really don't like, dogmatic, like you should always do a sync and never do live and this and that. Like, I think it's always a mix.

Yeah. I like the idea of the IRLs and maybe what kind of touch the internet a little bit later. it seems again from the experience that people have had the last two years with what they call remote, which obviously isn't remote, their concept of remote it's okay. You never see each other ever again, this person, that's it. If you, if you met them in person that would be thankful for that. You never gonna meet them again. Where is remote leaders who doing this long time, those IRL, those opportunities to meet face to face for remote teams are crucial. when I was with Invision, it was something crucial that we had to do. the company did a couple of those company wide and smaller teams wide. And I was an advocate for that, since, I was the first employee there and certainly know from, from what you're saying, having those opportunities to meet the team in real life is absolutely crucial. And I think a lot of people really miss that, at least the last two years it's okay now I'll never see you again. I'll never see your face and that's just the way it is.

[Brian] And I also think it's important to have that personal, chemistry, you know, there've been a few times when the person that I hired or that I'm working with is super talented. They have all the right skills. but we just don't have good conversations. We don't, we just don't gel. I don't know what it is, you know, it's just some people like that's how it is, you know? and, and it did unfortunately make it more difficult to, to work together. Long-term, you know, I think, I think obviously you need to hire people who have the right skills. Like th those are the people you're going to pick out of the top of the funnel of the hiring. Do they check the box on the, on the skills front? Yes. Then it's okay. How do they communicate? How do we communicate together? and whatever we can do to facilitate that, to see, you know, how well are we gonna cause communication does everything. It doesn't matter. Even across every role developer, designer, writer, you know, account manager, whoever it is like you have to be able to communicate with your teammates. and, and if that can't happen, it's just not going to work.

[Scott] Yeah. I think that leads me into my next flight. It's again, one of the negative feelings I had gotten from the same kind a podcast about going totally in on the async high-earning is that idea that what happens to the idea of the team, right? Again, for cultural fit and all the things like that. And you want a person to be part of the team and you have a shared mission, and you're all working to make the company mission successful. And again was shoulder to shoulder. And you can imagine, no, Michael Jordan, when he was part of the bulls, he had no one was coming to pick them. Then Steve Kerr and he was surrounded by a fantastic team, even though he was the best player. Then when it goes to Washington, it's all by himself and you see kind of two different players. So I feel like this is kind of that slippery slope, that people, again, who haven't done this, we haven't done remote.

We haven't done asynchronous before the pandemic. We're kind of picking it up now. They're kind of getting in that train and there's a real slippery slope there. That again, I think it's, if you're doing async by, by default, but then you will have the opportunity for synchronous where you need it, but people were kind of just going on a train saying, yes, this is the way we're going to go. We're going to do everything asynchronous. I'm afraid that it's going to totally fall off the track. No, it's going to be separate Congress in the machine or the cogs don't work together. It's just me, I'm doing my marketing job. You're doing your customer support thing and we have no interaction and we have no partnership. We have no tick, like what has to happen to company? What had happened as a culture, what has happened to the mission? I mean, you feel as if it's even possible to succeed in a, in a culture like that, where it's totally isolated people who have nothing to do with each other and don't really care and just go for it.

[Brian] Well, I, I think, you know, I think again, there, there are, I think it's really important to, to have a regular cadence of live interaction. so like the P so now that I'm working with that marketing person, like, we're still making a point of actually having a brief live zoom calls probably once every two weeks, you know, it's like his early morning, my late afternoon, but, but we can make that work just to have that connection, just to basically talk about the MBA, you know, and not even really talk about work and, but, what was I going to say that I also think that async communication can and should raise up a level now with the help of a video and more conversational aspect. Obviously that's, that's what zit message is all about, but you know, is not new.

I mean, slack has been around for a very long time. Email has been around forever, you know, that is asynchronous text message, SMS, text messaging, that's asynchronous, right. People are used to text-based async communication. but that's not enough. Like you, you, you can't be only text-based, communication, you know, you can be somewhat productive. Like, you know, I have worked with like developers and most of our communication happens in written like GitHub issues and things like that. But, but you know, longterm, you still need that, that live interaction. and I, and I think that to have, again, like getting back to like the collaboration and, and, and adding the most creative ideas that there is a balance because it's like, you know, I think part of the benefit of, of asynchronous is to be able to, to give each other the space, to have the deep creative work that the deep time and creative work, and to leverage like video conversations, you can still have the face-to-face fidelity and sharing your, your best ideas are showing on your screen without having to always resort to a live zoom call, just to get the face to face video aspect.

Because when you, when you overly rely on that, then you're packing people's calendars or making them work even later than they normally would because they're compensating for the hours that they had to be pulled into meetings. I mean, zoom fatigue is that is actually a real thing, you know? And so, especially when you're dealing with creative, members, and really everybody is creative now, it's not just designers it's if you're, if you're a marketer, if you're, if you're a builder or a product person you're, you're, you know, you're creative. and so, you know, like there has to be space to actually do the work. and I think there's a big issue with maybe this was one of your other questions coming up, but, the shift from in-person to, to remote kind of results in like more zoom calls, more meetings, because it's like, people don't trust each other that they're actually, if they're at home, are they actually working?

You know? and, and frankly, I think that this was happening even before the shift from in-person to remote, because I think there's still a lot of remote teams who, who really rely pretty heavily on tons and tons of live calls, you know? and I, I just don't, I just don't really get it. Like, for me personally, I can't have that many meetings on my calendar. You know, I do have calls, I talked to customers, I talked to people sometimes, but like, sure. I, I need that space, you know, and I think the team, and, you know, we're also, I'm just going to keep kind of ranting on this a little bit, but like, we're also w you know, in what people are referring to as, as the great resignation right now, right? Like people are leaving companies because they're rethinking, well, what type of work-life balance do I want?

What type of, what type of work experience do I want? You know, they're, and, and one thing that I've learned from years of building my companies remotely is like, there are really, really talented, driven, motivated people who don't want the structure of a corporate, office. So, so they seek remote work, but they also seek flexible remote work, like their stay at home parents, or they just prefer to work at night instead of the morning, they like to work out or travel or whatever it might be. they can still deliver really amazing, like professional level world-class work, and, and, you know, not, not being an office and not be, Hey, I'm looking at you. I see you're online right now. So you're definitely working. No, it's like, yeah, I see you're working because you're delivering awesome work, you know,

[Scott] Exactly it at heart of the future. Certainly a remote work it's going to be based on deliverables. it's clear to them clear deliverable, clear timeline that equals productivity. I've been saying that it's a math equation, right. One plus two equals three. but I think it's in general, I think we're at the cusp of the, certainly the greatest revolution to work since the industrial revolution where we're hopefully now getting to the point where, especially in the Western world. And unfortunately it was always, you lived to work, which is, has been what it is, but we're now I think getting to that point where now flipping that on its head and finally getting to that point where we're working to live. And I've been saying through the pandemic that post, post pandemic, remote leaders like yourself and other remote leaders, we need to kill off the word remote work, and now remote life.

It's the location independence now allows me to live the life that I want to live. That makes me most happy, makes me most productive. And we've seen this outside of even remote work, you know, even across the news of the logistical issues and ports and truck drivers that are aren't available in the U S because they can go get a job and, and drive the, know an Uber for three hours in the morning, and then three hours in the evening. It's, it's less the money that they're making, but it's, Hey, I take my kids, I do my thing in the morning. I drive Uber for a couple hours. I go pick up my kid. I go to lunch with my spouse. I go to the gym, I do that. I drive a couple hours. I get to live the life that I want to live now. And the work enables me to do that versus for historically, has been kind of the opposite way around. And it's a, it's a beautiful thing to see.

[Brian] Yeah, absolutely. yeah, I mean, I like the idea of like, kind of killing off like remote work and it's, it's just work, you know, it's just like, that's how work happens now. it's almost like weird if you're actually in person, you know? but, but yeah, and I think, I think you're, you're seeing more and more people. I mean, really it's just the pandemic who knows what kind of mass, like psychological effects this has had on people. But I think what we're starting to see with this like great resignation is like for the first time people were forced out of their routine of just sticking with whatever they've always done for work and they're, and they actually can, can step back and think like, does that work actually make me happy? Am I doing work? That that is best for me, that, that I'm best for that type of work.

Like, I think people are finally starting to really think about that. and I think people in our industry, you know, working on the web, creating things online, I think a lot of us have had that sort of mentality, for, for a long time, you know, we're creative people and we do we're, we're, you know, I th I certainly, for myself, I I'd imagine for a lot of people, in this industry, you know, I, I've always been driven by doing the type of work that I actually love. And like, to a point where I don't think that it's work, it's actually really enjoyable. but, but I think more and more people are, are, are seeking that and, and it comes and communication is a huge part of that, you know? Yeah.

[Scott] Yeah. I think the lights had been, you know, bookmarked or you'd wake up maybe at five 30 in the morning, so you can go for a morning run, you get home at seven o'clock, you play with your kids for 20, 30 minutes before they go to bed. Like your, your life life was bookmark before and after a commute into Workday. And now it's just, it's kind of ingrained and intertwined. And I think that's just a beautiful idea that again, you're living your life and work is just a piece of that. It's not, not a bookmark.

[Brian] It always used to, it always amazes me. And this is definitely true before the pandemic. I live one hour north of New York city. And before I was self-employed, I did commute into, into Manhattan to work at a web design agency about an hour train ride each way. And you're from long island to you. You were, we were talking about this off, off air. I mean, we're talking about a train packed with people. You're standing up for an hour straight going into Manhattan and, and back, so that's two hours. So, so you're already waking up like two or three hours earlier than you actually have to get into work. You have to get onto this crazy trout crowded train, not to mention all the germs that we're now aware of. Right. but the, but then, then you, then you'd come home. You're, you're dead tired after commuting both ways. Now you gotta go to bed two hours earlier than you normally would because he gotta wake up and do it again the next day. I mean, think about how much of your life is cut out and that, and, and those extra hours are not even your act. You're not even getting paid for those, those, aren't your work hours. That's just preparing to commute into, into a workplace. It's kind of crazy when, when you think about it, you know,

[Scott] I think for, for the last question I have for you, it's bringing the backup points that you were speaking about earlier about the ideas of killing off meetings. I'm a big believer in killing meetings. I passionately hate them, but a lot of people who'd been speaking about this asynchronous and things like that are touting the idea of that, that deep work focus time. And that's like the big win of async, you know, without meetings, without having the expectations for reply. It's just, just you and the task at hand, I could just sit for seven hours, eight hours, and my whole day kind of just doing what I need to do to get this specific job done, but I don't really hear them or anyone else speaking about what, how do you maybe take that time that you save for getting rid of that weekly meeting and turn into team building? So that's, I think a big issue and that's, again, something that I've been promoting it's when you get rid of that and a weekly meeting for an asynchronous document, if you don't kill the meeting slot, you just now play a game, you do a Netflix watch party. Like you do something to build the comradery and the bond between teams. but if companies are going again, focusing on async, what are your thoughts of, how do you build deeper relationships and trust?

[Brian] I really like what you're saying there for first of all, number one, the, the whole idea of like deep work and having space in your calendar and, like the convenience factor of, of a sink, that's, that's a benefit, but it's not the main benefit of, of async it's it's, you know, it's like, like, obviously if we're not having a live meeting, then you're going to have more time to actually focus for an extended period of time. and that's really, really important for, for lots of different types of work. Yeah. but that should not come at the cost of actually communicating. And that's why I think like, you know, w whatever, it may be like a daily Mo multi times daily, like sending a ping, whether it's in slack or showing your work on it on a zip message, conversation, whatever it might be, but, you know, it doesn't have to be live.

So I really believe in that, but what you're saying about the team building stuff, I think, I think where that can become more effective and more impactful is if you're not seeing your teammates in live work meetings all the time. Yep. And then, one at a five work meetings has to be a team team building meetings, and then it loses its impact. But if, but if the only time, or one of the only times that you're really seeing and hanging out live with, with your team members is when you're doing something fun. you know, instead of, instead of a live meeting, cause the live, the, the work meetings can, can and should be asynchronous, but the interaction, the, the comradery, the fun, yeah. That's where, that's where the, the live stuff is really useful. So I think it makes it kind of 10 X is the impact of those. If, if it's like, that's when you get to hangout live, you know?

[Scott] Yeah. I completely agree. And people I've spoken to who are in that deep work time, it's not that they don't want the distractions. And again, maybe I'm, I'm an extrovert. So maybe I see it differently than maybe someone was seeing it as an introvert. And I launched personally launched a side project maybe about two months ago to try to recreate those serendipitous five, 10 minute conversations called Spontaneousli. you had at the water cooler area had enough hallway, random conversation, meet somebody, bump into them, short conversation, very easy because at least for me and my years of working in the office, that I, I try to avoid thinking about those were core. For me, those were super important. Every hour, hour, hour, getting up, going to someone, if someone's desk having a five minute conversation going to Starbucks, no once or twice a day. And again, it's when it's focused on like async, async async and deep work, deep work.

How do you find these little opportunities just to have a conversation with somebody just to build trust with somebody, how to build a deeper relationship? I've been trying to bang on the strum. no, as much as I have been for async it's again, async is wonderful, but it's it's work, right? Because companies have used video for the wrong reason all these years. They used it for work, but now you need to use it for team building. So now hopefully once async tries to solve that communication and engagement for work, now you need to just, okay. And how do we now do this for the engagement? How do we do it for team building and not kind of just say, okay, forget about it.

[Brian] Yeah. I mean, I really like the organized events of like, Hey, let's all go out to dinner together. Let's, let's go to, let's fly to a city together and hang out. I also liked the events of like, sometimes you have like a zoom happy hour. That's kind of fun too. but I also think that like, things like slack, like I like different tools for different different async tools for different purposes. Right. So, so zip message I find is really great for, conversations, especially where you need video and sharing screen and, you know, great for like reviewing work and giving feedback on work or having a hiring conversation to interview. but slack is, slack is not great at those kinds of things, right? Like you can't go too deep on slack and, and it's also kind of noisy, but where slack is helpful is quick questions throughout the day or, or, Hey, would you do this weekend?

Here's some photos of my kids from the weekend, you know, like whatever that might be, in slack it's, it's like, it's like more fast, fluid conversation. Doesn't have to be super important or super logged somewhere. you know, and then you get into other places, whether it's like GitHub or your project management tool, where you're talking about a piece of work. and, and that's where, where that sort of lives. So, yeah, it's a different, different, I think people are, are getting more and more, what's the word, like just savvy with like the, using different tools in different ways as, as we're communicating and working together. Okay.

[Scott] Yeah. I agree. rapid fire section, like I asked you five rapid fire questions, first idea. I think that comes from the head. Go for it. You ready? All right. Excellent. Number one. who's the one remote leader that you look up to and why?

[Brian] you know, really the first one that, that, and still through this day is Jason fried from, from base camp. sure. he he's really, him and David had have taught. I mean, they have a book called remote. but even before that, like they've been talking and, and sharing, all of this, all of these ideas that we're talking about today about, you know, one of the ideas that really resonated with me that Jason wrote about years ago, he called it like the slow meeting and what he was talking about was an asynchronous meeting. He was like, most of our meetings at base camp are slow. Meaning like they happen over email or, or asynchronously over a couple of days. You don't have to be live. And that, that really resonated with me big time.

[Scott] Awesome. question number two, what's your go-to source for tips, tricks, knowledge on doing remote the right way?

[Brian] well, I don't know about specifically remote, but just in general. whether it's getting business, tips, design development, product tips, I kind of live on Twitter and that's where I connect with most people. but it's also a lot of, friends in the industry who have become I've, I've developed a lot of really close friendships with people. and we actually hang out in person a couple of times a year, and we, we have private slack groups and stuff that we, that we've talked together. So that's where I get the most insight and information these days is, is talking to people who either have done similar work or are currently doing similar work to me. and, and I re I've always learned the most from watching other people work and following what, what they're working on and taking away like inspiration and ideas for me to figure out on my own over here, rather than like, kind of subscribing to, like, a training or a course, or, you know, I I'll read books sometimes, but like, I really learned so much more from actually working myself and seeing what other people are working on

[Scott] And like, question number three, if a company was, approaching you saying that they wanted to go all in, on being a remote first company, what's the first thing that they should change about how they run the company?

[Brian] well, they should go to zip They should sign up for an account and

Excellent that,

[Brian] That, that would help. you know, I think that it, I think the first thing that, that you need to start to think about is trust. You know, I think the reason why so many companies default to, okay, we're remote now, so we need to have more meetings. It's, you know, you have to step back and question like, well, how much do I trust my people? And, and really that's like, kind of how, how much do you trust yourself to hire the right people? Right. if they, if they've been great in person for years, they're talented people, they're not just going to stop working, you know? so, so I think it's worth, you know, trying it out, get it, of course it takes some getting used to, to not see the person all day, but, see how it goes and, and, you know, and I think it's also helpful to be intentional about like, look now that we're remote, we need to communicate in these ways. And that might mean sending a few extra messages than you normally would if you're in person, but just to let people know where you're at and what you're working on. but still keeping that space so that we could actually work.

[Scott] Totally, no intentionality was the number one word that came up across 20 something episodes last season. That was number one word that came up. This is how you do remote the right way. Everything has to be intentional. number four, it's, what's one thing that folks get wrong when they talk about remote work.

[Brian] yeah, I think, you know, we've been talking about it, but I think that remote often results in more meetings, not less meetings. Yep. I think it's, you know, again, like people sort of compensate for not having an office by having more zoom calls and, and I don't think that that's the answer.

[Scott] Totally agree. Last question. Easy one. do you feel that the days of having to go back into an office are really done and over?

[Brian] No, that's a really tough one. I think that I, my, my gut tells me that they are that, so all of those companies that, that were never remote before the pandemic, and they were forced to go remote. I, I would say the vast majority of them would either remain remote or, or where they call it, like hybrid, you know, allow, allow some people to be remote sometimes. you know, I think that's happening even more than, than people expected. I think a lot of people expected people to sort of just returned to the office. I mean, that being said, though, I don't blame companies for calling their employees back to the office. If that's what worked for them for a long time, it might mean that they lose some people. But I know that there are other people who work really well in person. I, I personally like I, I had a good experience working in person back, you know, years ago when I worked at a company, I tend to prefer remote myself, but I have friends who's actually still prefer like in person collaboration. I remember reading a couple of months ago, apple, got a lot of flack for like saying like, okay, we're going to start calling our employees back to the office. I think they were, I think they went back to my three days a week or something like that. Yeah.

[Scott] All for the big four, these all have the same policy. They're saying they're coming back to the office. They all had a revolt in mutiny on their hands and they'll have the back away saying, okay. A certain percentage will get to work all the time or three to, I personally think a three, two models is dead before it ever starts.

[Brian] You know, I, I just think again, for me, it comes back to like the, I just don't like dogmatic, like, like I, I can't blame apple for they've. They've been extremely successful, in, in, in their beautiful campus in California. I mean, like to, to ask their employees to come back and work there, the way that they have before the pandemic, I don't think that's the end of the world. I, but I get why buy, why it's not for everyone. but like I th the idea that this massive organization is going to, suddenly flip the switch to be a hundred percent remote. I don't know.

I don't, I don't work there, so I, I can't speak to any experience, but, it just seemed,

[Scott] Yeah, I didn't get to the point that these companies had spent millions of dollars in pulse surveys and employee feedback and get know, trying to get the insights from the company and their employees are sending an absolutely crystal clear message, 30, 40% saying I'm never coming back. The back to the office, have a nice life. 30, 40% are saying, I expect flexibility in where I work. And when I work, I'm the one who gets to decide. So there's an absolute clear message that the future is all about flexibility, but yet companies are going off on the other foot, coding, not listening to that saying, okay, there's going to be a three, two, you're going to have to be in the office on these days, or that day is coming back to the office. So for me, I think that's the biggest fault I would land on, on these, these large companies. They're saying your employees are absolutely crystal clear. They're not being forced back into the office. Again, if someone come back, they want to come back and how they want to come back. So you need to adjust how you're running your company to accept that because of 40, 30% are going to leave tonight. If you don't let them permanently work remotely and potentially another 30, 40 may leave, if you don't give them that flexibility to choose. I don't think there's any company that could replace that many employees, that quickly.

[Brian] I don't know. I mean, I've actually never really worked for that large of a company before, so I don't know what it's like. but yeah, it's, it's, we're, we're, we're living in a kind of exciting and kind of chaotic times right now, for sure.

[Scott] So Brian, how can people find out more and connect with you and zip message?

[Brian] So, Twitter where I hang out mostly I'm, I'm at @Casjam jam on Twitter and, you know, it's, it's that That's where the product is. and I, as you said, I, I, co-host the bootstrapped web podcast with my friend Jordan, and we just kind of talk about what, what we're working on.

[Scott] Amazing. So we'll be happy to include all those items in the show notes and Brian, again, thank you so much for the opportunity to speak today and being able to share your journey and hiring asynchronously and what the right format that you've found to be, and really kind of mixing the synchronous into the asynchronous and kind of being that journey moving forward. So certainly appreciate you sharing that with our listeners and yeah, it was great to connecting and again, a big fan. So thank you so much.

[Brian] Yeah, Scott, thanks for having me on, I think it's awesome that you're, that you're just focusing on, on async and this topic right now in this season. I, I think it's a really great, I, you know, most of the podcasts I do, we kind of brush over it for like five minutes, but I, I love the deep dive on, on asynchronous, so awesome. Yeah.

[Scott] Yeah. Very much trying to focus that on hybrid, it's the two big things, but, yeah. So thank you again so much. And until next time everybody have a great date. Thanks. Again, everybody for tuning into today's episode of leading from a follower. If you enjoyed the podcast, you can learn more on our website, leading from and subscribe to the podcast in your favorite app. This podcast is all about you. The remote leaders. We'd love to hear from you with your feedback or ideas for future topics and remote leaders. We should be speaking with.