In this episode, we talk about what challenges people and companies face when they make the decision to go remote.



Original transcript

Welcome to the Collaboration Superpowers podcast. My name is Lisette and I’m interviewing people and companies doing great things remotely. Hey, everyone. Thank you for joining me. In the last, short podcast episode, I talked about why people and companies are making the choice to go remote. This week I want to dive into what the challenges are that people and companies face. What’s so hard about working remotely?

Before I dive into the details, I want to talk in general about the change in mindset that’s needed when we go remote. One of the biggest shifts that we need to make is going from time-based working to results-based working. So it no longer matters how long it took you to do that marketing report. It only matters that the marketing report is done by the deadline and that it’s high-quality. Now saying, “Oh, just switch from time-based to results-based,” sounds really easy, but this is a huge challenge. Being paid for time spent is a pretty easy calculation. But being paid for value delivered starts to complicate things a bit. There’s a fantastic podcast episode on the Jacob Morgan podcast, episode number 46, that talks about how the gap went from time-based to results-based and the challenges they face but the results that they saw. So while this is a challenging problem, it is one that needs to be addressed when we go remote. When I ask people why remote working isn’t allowed at their company, the answer is shockingly fast and direct. It’s always management. Now to be fair, making the shift from co-located to remote isn’t easy, which is an understatement. I mean on top of whatever challenges we’re already facing in the office, going remote will add a whole, new set of issues, and that just takes time to work through. How is the team going to communicate? How will we know what each other are doing? How do we keep that sense of team? And most importantly, what’s in it for the company? All very fair questions. And let’s face it. Managers who want to offer flexible work options are taking a risk. If something goes wrong, they are responsible. So yeah, I can understand the hesitancy of management to implement and start flexible work options. But as we know, flexible working is the future. So just because it’s hard and just because it’s a risk doesn’t mean that it’s something we need to ignore. So yes, while managers do play a role, it is absolutely not fair to cast all the blame on them.

One of my favorite quotes comes from Jurgen Appelo when he says management is too important to leave to the managers. And I really like that quote because it says that it’s all of our responsibility for making our teams and our projects thrive, co-located or remote. So let’s dive into the details about what’s so hard. I’ve divided this into two categories. The first is what’s so hard for people who go remote, and the second category is what’s so hard for companies when they go remote. I hear this a lot. When people first go remote, they often think how hard can it be. I mean you’re just working from home or from a coffee shop. What so hard? But as many telecommuters and freelancers, entrepreneurs, and digital nomads will tell you, it’s not as easy as it looks. Yes, we have the freedom to create our own schedules and design our own spaces and choose the work that interests us most, but with that freedom comes the great responsibility of actually producing quality results. And when we work on our own, people tend to struggle with discipline, isolation, being always on, and finding a productive workspace. So let’s talk about that a little bit. We’ll start with discipline. You know that ability to set a schedule and stick to it and stay free from distractions, that ability to get the work done when no one else is watching, especially when the work isn’t fun, I think discipline is one of the major challenges that people face. And some people are better at it than others. So it’s not a judgment in one way or another, whether you have discipline or not. But you have to recognize what type of person you are. And if the structure of an office really works for you, then stick to that. I’ve heard from a lot of remote workers that isolation is really a problem because we’re working on our own so much. And people naturally crave human contact. So even when you’re working with a team of people and you’re using video, there is still a sort of isolation of being virtual. There are many things that we can do to not feel isolated, but that’s going to be a topic for another podcast episode. A big downside of being able to work from anywhere means that we can and tend to work around the clock. It is surprisingly hard to set our own boundaries and stick to them. Again, there’s that discipline thing. But really, when there’s no one watching or keeping us in check, it becomes our own responsibility to figure out what our limits are and then stick to those limits and communicate those to the people that we’re working with. I’ve heard words recently like telepressure and technostress, which I find very amusing. But it does highlight a certain truth to the dangers of being always on. I came back from a vacation a couple of weeks ago and since then made the decision to not check emails and social media on my phone first thing in the morning. And I have to say it does make a difference in terms of my attention span and total energy throughout the day. Therefore, boundaries of this kind are putting things in place to help keep our minds focused and fresh. There is a balance there. And different people have different boundaries, so it’s really up to the individual to set their own boundaries and then stick to them.

One of the last challenges that people face when they go remote is finding a productive workspace. It takes a little bit of time to figure out what kind of environment you are most productive in. So does it need to be quiet? Does it need to be bustling? Does it need to be sunny? Does it need to be natural light? What do you need to get your work done? Do you need external monitors? Do you need a webcam, a headset? All of these things need to be taken into consideration when we work away from the office. I really enjoyed the story that Jesse Fewell told in episode 80 when he first started working from home. He began by creating an office in his attic and then decided that the attic was too short. He’s a tall guy. So it just wasn’t working. He kind of felt crouched all day. So then he went and built the office in a corner of his bedroom but then found that he wasn’t leaving the room all day and eventually made a decision to actually build a small office in the backyard. And that has worked very well for him.

So when people first go remote, I just want to remind people that it can take time to figure out what your personal preference is and working styles are. And of course we probably want different environments for different tasks, right? So now we have multiple workspaces to figure out, nothing that can’t be overcome but certainly a challenge. Okay, so while individually, we struggle with discipline and isolation and productivity, as teams, there is an entirely different set of problems, most of which are centered around communication and team-building. Okay, communication is hard even when we work together in the same place. I’ve never interviewed a single team, co-located or remote, that has said to me that their communication was flawless. It’s just the nature of the beast when we work with other people. But it sure is efficient to be able to just look over your shoulder and say, “Hey, Bob, what’s the status of that report?” I mean that is high-bandwidth communication, right? On top of that, the people around you can hear that you’re asking Bob about the status of the report. And those conversations that we overhear in an office can be just as important. When we go remote, we have all kinds of obstacles that get in the way of that smooth, high-bandwidth talking. We’re fighting bad Internet connections, people with background noise, software glitches, time zones. I mean add to that language and culture, and it all kind of feels rather hopeless, doesn’t it? You can visualize it like all of this information is getting squeezed into a tiny phone cable and then spit out at the other end. I mean all that information around emotions and body language, it’s all getting lost. And of course if you’re a listener of this podcast, you know that there are lots of great things and tools to help with these conversations. But let’s be honest, technology is moving at very fast speeds. And trying to keep up with all the new apps and gadgets that are out on top of our workload already is a lot to ask. One of the things that I find most challenging when I give my workshop at some of the bigger companies is dealing with all of the security issues. Many, many very good tools are simply restricted by the IT departments for security reasons. And maybe there are good reasons, but it’s also really binding the hands of their employees. So yeah, communication is a huge struggle for remote teams, no doubt about it.

And the other thing that’s really hard is creating a sense of team when we go remote. It’s so much easier when we’re in the office together. Seeing and being around each other inherently creates a sense of team. And when we go remote, we have to work extra hard to build and maintain that sense of comradery. How do we create spontaneity? How do we learn about each other? Is it possible to have chitchat remotely? And most importantly, how do we build trust with each other when we’re remote? That’s a huge one. I cover that quite extensively in episode 81, but I’ll give you the basic overview here because it’s such an important issue. I always say that trust comes down to reliability, consistency, and responsiveness. So can I rely on you to get the work done? Can I count on you to do work that’s of high quality? And can I find you when I need to? When a team has trust, they operate as a cohesive unit and they look for ways to help each other succeed. A lack of trust will manifest itself with people not talking to each other or withholding information from each other and disengaging. And that’s a recipe for doom. Definitely, don’t underestimate the importance of team building and trust building on remote teams because these are your critical pillars for remote team success. So now we’ve talked about what’s hard for individuals and we’ve talked about what’s hard for companies. And I want to end by listing some of the general challenges that we have when we’re a global team. Number one on the list, time zones. It’s hard for everybody. Time zones are a mess, and we simply need to be extra careful on remote teams to get that right and to recognize that, we’re going to screw up sometimes. I mean I must say I get a time zone wrong at least once a month and I double-check and I’m supposed to be a pro at this, but it just happens. So double-check and have some understanding when things go wrong.

The next thing that’s very hard for global teams is payment. How do we pay people from different countries? What are the tax regulations around that? This stuff is a challenge to figure out.

Another challenge of going global or being global is dealing with culture and the differences in the styles of how we work and live across the globe. I recommend listening to episode 88 on the podcast where I talk about how to discover the culture on your virtual team. And I go into all kinds of tips that I’ve collected from the interview. So of course with all of these challenges, there are things that we can do. But I just wanted to focus today on what’s so hard, and culture is really hard.

And the last thing which goes hand-in-hand with culture is language. Differences in language and accents can be a real challenge on a global team. Again, I talk about some of those tips in episode 88 as well. Okay, I hope you’re not all feeling hopeless with all the things that are so hard about working remote. Plenty of case stories out there of companies who are doing great things. So don’t despair. It’s simply good to recognize what the struggles are so that we can deal with them. And if you want to learn the details of how to deal with them, there are a number of different options. One, you can go back and listen to the back episodes on this podcast. I give tons of great tips and tricks for how to create successful, remote teams. You can pre-order the book, Stories Of Remote Teams Doing Great Things. It’s coming out soon, I promise. And when you pre-order, you get a hard copy of chapter one in the mail as long as supplies last.

And the last way to learn how to overcome all the challenges of going remote is by taking the Work Together Anywhere workshop. I’m very excited to say it is now offered in 18 countries and seven languages. And you can take it online, so there’s no excuse. Find an event near you at

Stay tuned next week when I interview another company that’s rocking the remote world. A big [ol’ – 15:01] American thanks to Nick, the podcast monster. He produces this podcast and makes it all pro. You can hire him to make you a star at And another shoutout to the incredible Alfred Boland who just makes Collaboration Superpowers look great. He’s the graphic designer, and he’s the one that makes me look so cool. You can check out his work and hire him to make you look so cool at All right, everybody. Don’t despair. The challenges can be overcome. I’ll see you next week. And until then, be powerful.


Podcast production by Podcast Monster

Graphic design by Alfred Boland

Managers, Podcast
Share on Facebook0Share on Google+0Tweet about this on TwitterShare on LinkedIn1Email this to someonePrint this page

This article is written by on