Ryan has a great set of techniques for behavioral interviewing, when meeting candidates, which he details here. He also has great advice for remote worker hiring, in terms of the […]
Why I created this podcast
This episode digs into how 2020 looked as remote went mainstream, albeit somewhat forcefully. Stefan is a writer and thinker covering remote work trends from before the pandemic and shares unique insights.
Stefan is a writer and entrepreneur passionate about the future of work. He started writing through his thesis research at Yale University and since then has interviewed over 250 entrepreneurs and produced over 1,000 pieces of content for B2B startups, venture capitalists, and tech media outlets as a freelance writer. He’s also the author of The 50 Laws of Freelancing and publisher of Remotely Inclined.
I talked with multiple employees who had gone to remote than my friends, people on Twitter, et cetera, and they’re like, oh my God, I just hate remote work. I want to be collaborating with my coworkers. I want to be able to work from a cafe. I’m tired of being at home. And a lot of instances I had to say, wait a minute, you realize that remote work means you can work from a cafe or remote work means you can go into the office if you want to.
The real fundamental premise of remote work is just that you’re not tethered to an office, that it’s not an absolute requirement, but a choice. You are listening to the online remotely podcast, the show dedicated to helping lead distributor teams under difficult circumstances. I’m the host Look Sharp and I’ve participated in a run distributed teams for almost a decade. As a practitioner, I’m speaking with experts on leadership, strategic alignment and work to help you navigate the issues start facing after you get.
You’re welcome, welcome. Today on the podcast, we are speaking with Stephanopoulos, who is a leading remote essayist, journalist and thinker covering the topic. I enjoyed his pieces. They were quite thought provoking throughout the year. And I thought right now would be a great time to conduct a retrospective across the year that everyone discovered remote together with him. So on this episode, we cover why coronavirus has actually been a bad thing for remote work. We cover how to thrive as a company rather than just to survive the pandemic, and also how to use tech tools to recreate your office dynamic.
Tune in and let’s get on with the show.
Welcome to the podcast.
Since both of us have been in remote work for a bit longer than just this year, I think it would be interesting to hear your take on what happened this year. How did you get into the topic of remote work in the first place? Yeah, absolutely.
It was by accident and by necessity. The short version of the story is that I tried to start a business in twenty fifteen that I ran bluntly for far too long. It was failing. The idea was OK, but the execution wasn’t there. I was inexperienced and ultimately put me into some debt. I took on a loan to help the business go forward and when it fell apart I needed a job. So I was working at a startup and then I had started freelance writing just very occasionally covering an event or two for a local media company.
And someone cornered me at an event and just said, Are you Stefan? And I’m like, Oh, God, did I write something bad about your company? Please don’t hurt me.
And you said, no, you’re Stefan. I love your writing. Can I pay you to write for me? And that was in twenty seventeen. So that’s when I actually started my freelance business, which is the business that I run today. And I had to go remote because I couldn’t afford the time to leave my office job to go see a client so remote for me was the only way that I could be an entrepreneur because I was in debt.
I could not afford to leave my job. I needed that salary at that time.
And that’s how I got into remote completely by accident. Like I said, I needed to be remote in order to be successful. So fast forward through that time from twenty seventeen to twenty nineteen, I was learning on the fly, figuring some stuff out. I was a solo printer so I didn’t need as much of the content of like how to hire remotely, which was a very scarce at the time, as you well know, pre covid we weren’t talking about it that much.
And so I actually didn’t talk about being a remote entrepreneur. I just did my business remotely. And to some extent I would even try and go on my lunch break around the corner to another startup client because my my clients were all startups in Toronto where I live. So I would try to show up to do that face time to almost make up for the fact that my business was remote and then came covid, which definitely changed everything and nothing for me.
So how I ran my business did not change. I was doing it remotely. Anyway, in twenty nineteen over the summer, I had run my business while on a trip to Europe and so I was on a different time zone running the business remotely and it just was the same. And that was something that my clients really liked about working with me during the early days of covid because it’s OK. Working with Stefan does not change. We can just continue that and figure out everything else.
But what ended up changing was people went from, oh yeah, like you’re a freelancer. I come show up at my office every now and again to wait a minute, you’ve been doing this remote thing for years now. Like, how the F do I do it? So to your question of how did I get into the topic? I stumbled into it because I had to.
I learned a lot of my own stuff. And then in late twenty nineteen, I started thinking, I want to put out content about remote leadership. And I call in my head, I called it remote leaders and it was just going to be interviewing other remote entrepreneurs on how they run their business, because I was curious how other people had solved this problem for themselves in the way the same way that I had solved it for myself. And that evolved into remotely inclined, which became this broader newsletter all about remote work and remote leadership in general, whether that was a team or a business or even just an employee trying to to make this whole thing work.
So that was the journey where I stumbled into it. I educated myself and then I thought, I want to put this content out in the world because I know how confused I was and I can’t be the only one. And then covid really just accelerated the interest in that topic in terms of the freelance business itself.
So you’re it’s primarily writing and or is there other parts to it?
There are a couple other parts. My my one liner is I’m a freelance writer for startups and venture capitalists, and that right now is the bulk of my business. But the other part that I wanted to start was one I don’t. Just write editing, content strategy, all the things that come under, I put words on a digital piece of paper, but the other piece is that similar to remotely inclined to this feeling that I was solving some problems for myself, I couldn’t be the only one.
I was having trouble finding news that was relevant for freelancers and understanding how certain corporate actions matter to freelancers. So I took a blog that I had already started just for fun called Pulse Blueprint and evolved that into news and resources for freelancers. So that’s now the second part of my business, which is helping other freelancers in the world learn a little bit more about what’s going on in a way that it impacts them. So those are the two areas of my business right now and then have a couple of growth plans for twenty, twenty one.
We shall see how they play out.
Of course, one thing I wanted to ask you quite frequently, differentiate between remote work under lockdown and remote work.
Can you explain what exactly you mean?
Yeah, absolutely. One of the first articles that I wrote for for a remote inclined, rather, was called Why Coronaviruses A Terrible Thing for Remote Work. And I published it in February. So before lockdown started, when it was when everyone was calling it the novel coronavirus, that’s how we knew it. And I looked at this thing and when yikes. And as some news started coming that some companies were starting to push their employees remote and just as a precaution, we’re not sure what’s going to happen yet.
I was thinking this is horrible because it’s going to associate remote work with being stuck. It’s going to associate it with a pandemic. It’s going to associate it with pain and suffering. If people are dying from this virus. Back in February, I didn’t know any of the numbers that we’d be experiencing now. It’s just a really bad thing. It might push people to consider remote work and that could individually be good. But on the whole, I don’t think it’s going to be good.
So as the pandemic evolved, I’d say that I was in general kind of on the mark, but I didn’t hit it one hundred percent. So obviously what has changed is that people are realizing they really like remote work and want to continue it. So my tone shifted a little bit from, OK, it may not be the worst thing in the world. I may have been a little off the mark there, but I am concerned that people are associating everything about remote work to the pandemic.
So, for example, I talked with multiple employees who had gone to remote than my friends, people on Twitter, etc., and they’re like, oh my God, I just hate remote work. I want to be collaborating with my coworkers. I want to be able to work from a cafe. I’m tired of being at home. And a lot of instances I had to say, wait a minute, you realize that remote work means you can work from a cafe or remote work means you can go into the office if you want to.
The real fundamental premise of remote work is just that you’re not tethered to an office, that it’s not an absolute requirement, but a choice. And that nuance I had, I found myself having to constantly explain whenever I’d say, oh, I’m a advocate for remote work, I think it’s a great thing. And people go, Oh, I hate it. Like, I hate being stuck at home. And it’s no, you’re in lockdown. You are working remotely in lockdown.
That is a different thing. And I would go into a personal example. Last year I ran my business from Europe on vacation. This year, I was actually back in Europe. I was in France running my business from the French countryside because I managed to get myself an Internet connection that is the power of remote work, or that I wanted to go to a coworking space in Toronto where I live. And so I did. And I invited my friends to come join me.
And we worked together and we collaborated. And that’s the power of remote work. It’s all about this notion of choice and lock down took away our choice and it frickin sucks bluntly. I hated what room, what lockdown did just to us as a populace to humans, but to the remote work movement.
And in that way I feel that I was accurate when I said coronaviruses going to be a terrible thing for remote work because it entrenched this idea that the first remote working experience for millions of people was under lockdown conditions. And that is not fair to them. It’s not fair because lockdown sucks, but it’s also not fair because they’re not experiencing the benefits of remote work. They’re just experiencing the downsides because remote work is not perfect with the remote environment, you have to be far more focused on how you create your own schedules.
You have to be far more self-motivated, both to start and stop work. But we saw a lot of information coming out a couple of months ago about how people are actually just working more during the pandemic because they’re sitting at their computer. So they just keep working and have nothing else to do in lockdown. So that’s what I mean when I harp on this idea that lockdown of remote work in earnest are not the same thing and that. Working remotely because you have to is a survival mechanism, but remote work is supposed to be about choice in how you work.
Interesting that you mentioned survival, that was actually what I was thinking of asking next in your podcast episode about the three levels of cost.
You mentioned that there is a difference between companies spending money just to survive through the pandemic versus companies trying to really make remote work. So let’s say try and thrive while remote friendly.
What do you think are the main differences between those two? Could you go into a little bit more detail in terms of them?
Yeah, I think the main difference that I saw between those two expenses is, one, how bitter someone was about it and then to what the outcome what the goal was. The bitterness is just if you have to spend for survival, you’re going to do it, but you’re not going to be happy about it. Whereas spending to thrive, you want to do it. But you’re you may not be quite as motivated because it’s interesting. As soon as you say spend money to get more, it’s this question of, I don’t know.
But if it’s spend money to avoid pain, then we are very eager to do it. So that was one more hokey, emotional difference. But on a more practical level, the idea of what do you want out of it? So if you’re doing any form of spending for survival, that’s going to be something like, OK, we need to urgently implement a collaboration technology because we found that our systems don’t work anymore because we are realizing we over relied on walking to someone’s desk.
When you get to the office, environment is all well and good, but you can’t do that in a remote environment. So they would spend tons of money on instant implementations and choosing a technology that it’s hard to assess if it’s actually going to help you in the long run or even solve all of your short term needs. It’s just that you saw that solved one. So you do it quickly. So, for instance, teams that suddenly wildly expanded their Slack’s or got Microsoft teams and then someone says that, OK, we whiteboard it a lot.
So now we need to get mirro and then, OK, we we like talking. So then we got back. And all of these technologies individually are very powerful and I would highly recommend them under the right circumstances. But my problem is not the technologies, it’s just that in survival mode you are buying and buying a buying with little intention. So you’re hoping that it’s going to solve the problem that can end with tech bloat. So you end up spending more money than you need to.
And it can also end up with usage problems where you aren’t using it in the way that it’s intended or in its most impactful way because you rush to get it done because you had to. And again, I’m not blaming anybody in this. Now, if you contrast that to spending a bit more intentionally, it can be the exact same things. Let’s say you set up a communications triage system, so you expanded your slack to only be for social conversation so that everyone knows when you get a slack notification, it’s probably a meme, whereas continuums is for your your professional communication.
So if you know that if you get a team’s notification, you have to check that because it’s going to be relevant to your job. And you use Mirro to actually whiteboard in controlled environments where you are collaborating on Microsoft teams and sending voice messages in your back and collaborating back and forth in an asynchronous way. And then you put it all in your mirrored board and it’s all part of a cohesive system. So it’s not about the tools because there are so many really powerful, valuable tools.
But the difference for spending for survival versus spending for thriving is what systems do you have? What intense do you have? And then are you actually buying what you need or just buying a symptom cover in the short term, hoping that it calms everything down so you can think about it later? I think in the earliest days of the pandemic, everyone just needed to survive. And again, I don’t judge anyone for their purchase decisions. I’m happy that companies were willing to invest this cash.
But what I’ve liked seeing later is companies saying, OK, we bought this because it’s going to help us do this, or we know that if we want to be successful, remote, we need to have more asynchronous methods, which is something that you and I talked about on our interview. He founded remote dotcom, which does administrative stuff for remote teams. And he said, look, if you really want to be successful, remote, you’ve got to have some asynchronous elements.
So then we have tools like Yaka or Mirro that can help. And it’s really just about the plan you have for the purchase was my main difference and how you actually are going to help people use it to solve an existing problem as opposed to buying technology, hoping that it will create things for you, if that makes sense.
Hi there. This is Luke. And just for a quick bit of backstory, this podcast is part of my process to create a book called. The line remotely, which will cover roughly the same topics as we have on the podcast, if you’d like a free advance copy of the book, I’d be more than happy to give you one. Just to be clear, it’s totally free. There’s eight chapters as of today available for presell and people are buying it right now.
And this offer will go away as soon as the book is fully launched. My main request is that you leave a review of the podcast using this podcast dot com slash align remotely. It’s designed to work on your phone, but you can do it at your desk, too. And then forward me a screenshot of the to customer success at a line remotely dot com and I’ll hook you right up. Just take a quick break rate this podcast dot com slash align remotely and get your free copy now.
It does. I did a good amount of my remote experience, more of a corporate environment. One company in particular was a Microsoft house and would always really confused me was they paid a good amount for SharePoint. But then there was like absolutely no configuration. It ended up being something that everybody would fight against in terms of how the searching for documents worked or something like that. It goes back to this point of actually being deliberate about it and then going and implementing it properly.
I was interviewing an entrepreneur and I forget this person’s name, so I apologize to him. But he talked about this idea of the random act of tech that you’re buying tech because you think you have to because you want to be a tech forward firm or you identify as a tech driven organization. Whereas what I found when people buy technologies to thrive, it’s usually a third order consequences. So they think about what they actually need to achieve. And that’s let’s say they need to have great ideas.
OK, so we need to brainstorm. And then they think, what does a person need to do to achieve that?
So in a remote environment, they need an asynchronous tool or they need to brainstorm asynchronously so that there has to be an opportunity for everyone to put in their best ideas throughout this time box so that we can all talk about it later. And then they say, what tool is going to power that could be mirro, for instance. So it’s that third order to avoid being this random act of tech. And as companies think about being more outcome oriented, which is critical for remote environments anyway, because employees need to be able to know what they’re doing and then do it.
Arguably the same problem in the office. But I digress. Once you think about the outcome orientation not just for employees, but the company first and then what are the employees need to accomplish to support the company? And then what tools will allow the employees to do what they need to do to support the company? That’s when you can start making technology purchases, and that’s when buying technology, particularly in a remote context, is going to be incredibly impactful.
In the same way. I remember one of my previous employers before I started my business, the office manager came up and asked me and said, How do you work? Do you like to if you have to brainstorm, what do you like to do? And I said, honestly, I’m a very visual person. I like writing things out. I’ve got paper strewn all over my desk. And she said, Oh, I’m just going to buy you a whiteboard.
That same process should apply to remote technologies. It’s OK, Stefan, how do you get your best ideas out? Well, I’m a visual person. I’ve got sticky notes all over my apartment. OK, why don’t we just get a virtual whiteboarding software? There we go. So it’s the that third order. What does the organization need? What do I need to do as an employee to support the organization or as the beta team leader, CEO, whatever my role is.
And then what technology is going to allow me to do that?
What do you think of the tools which are designed to fill gaps that people have because they’re working remotely as opposed to being in the office? I’m trying to think of a good example. So one one that’s come up. I haven’t actually used it myself, but I’ve heard it mentioned a few times. Don’t add up as a tool that helps to people randomly within a company random and run into each other.
What do you think of that whole trend?
Yeah, it’s funny you bring up Donut because I actually got introduced to donuts in an office environment in a startup that was very explicitly anti remote work or telecommuting or whatever term they used at the time. And the company was growing very quickly. And they used Donut as a way to foster culture in a fast growing company where there could easily be someone fifteen desks down from me that shows up one day that I do not know. That is in a different onboarding class.
So it’s interesting that these companies have rebranded to being remote work culture builders. And I again forget who said this first. It’s not my saying, but it feels like remote washing in a way where similar to greenwashing, where companies all of a sudden market themselves as environmentally friendly or. Washing, which is the is marketing themselves as LGBT friendly because it’s pride month, remote washing started happening a lot in April, May, June twenty twenty, where every company was like, yeah, we’re a remote solution and don’t that’s an interesting example.
And again, I am not trying to bash Donut. It was a perfectly fine app, but to pivot from, we help you build office culture and meet your colleagues to wear a remote solution is an interesting one that I think is smart. You’ve got to go where the search intent is. People are looking for remote solutions. I don’t judge anyone for that.
But the premise I question a little bit, I really like the idea that people are trying to help co-workers connect. I think where I start to have a bit of skepticism is a bit more around. Does that gap a need to be filled or is remote work just fundamentally different? And maybe that gap is less relevant and then, B, if it does need to be filled, does it need to be filled in the same way that it was filled in an office?
So one big one that we’ve seen a lot in the remote world and is starting to come down the pipeline to the to mainstream communication, is this idea of asynchronous meetings. So in an office environment, we said we built a culture over the past 20 years, especially of, oh, do you have a few minutes? Just want to, like, quickly chat with you about something. You walk over to someone’s desk or you book twenty minutes and someone’s calendar and you have your live chat, your synchronous chat.
And then if we imagine that is a gap that needs to be filled and arguably, yes, it is. People need to be able to collaborate instantaneously with colleagues or at least top someone on the shoulder to collaborate more generally. Does it need to be filled the exact same way that we filled it in the office? And arguably that answer is no. We saw evidence of this with the massive rise of zoom fatigue and this idea that a human can engage face to face in person for far longer and be far more productive than doing the exact same thing, staring at a screen and how more and more research was coming out.
Microsoft actually put out a study, I believe it was in July or August, that their proportion of our long meetings decreased significantly and whenever an hour long meeting was booked, they would get more and more questions of what is this meeting for? Why do we need an hour? I don’t want to stare at a screen for an hour. It hurts my eyes, whatever it may be. That is some interesting data that suggests, OK, yes, the gap needs to be filled, but does it need to be filled the exact same way remotely as we did it in the office?
And I think the answer is no. A lot of other people think the answer is no. And the solution instead is to consider asynchronous meetings. So send in voice notes back and forth on back or send illume video or write your ideas in a mirrored board and then have everyone pop in and send a message with a time box for reply instead of an expectation of an immediate reply.
So there are lots of ways to get that done. But the premise of did it need to be solved? Probably, yes. Did it need to be solved identically to the office in that one case? Arguably no. In other cases maybe. And that’s where tech can be helpful. So instead of tech coming in and saying, here’s what you did in the office, we’re going to make that easy remote, I would like to see more questioning of do we actually have to solve this problem?
And if yes, do we have to solve it identically to how we solved it in the office? Because if all we do is just this quote unquote remote washing and say, oh, our technology powers, remote teams, we could end up with even more of that situation that I mentioned earlier where people are buying technology to solve a problem that may not need to be solved or may not need to be solved in that way for optimal performance. And then we end up with more and more.
I hate remote work and it’s do you or do you just have the wrong tools? It’s a square peg in a round hole. Exactly. So that was a great discussion with Stefan and we will continue next week, wrapping up the year. But from this part of the discussion, I think my biggest takeaway was. Actually, the necessity of some element of async, if you want to be successful, one remote also have a quick announcement, a line remotely the book is launching on Amazon on January 4th.
There’s going to be a giveaway of tools for remote managers and the details will be announced to a line remotely subscribers only. If you are interested in participating, then please sign up at a line remotely dot com where you can leave your details and you will get the information shortly before Christmas. Tune in next week for part two of this interview. Thanks for listening to this episode of the online Ramogi podcast, if you enjoy the show, please leave a review on iTunes, Google podcast or wherever you get your podcast.
Ryan has a great set of techniques for behavioral interviewing, when meeting candidates, which he details here. He also has great advice for remote worker hiring, in terms of the […]