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Intro

While still in college (go Broncos!), I teamed up with Alex (@slevenbits) to create a startup. We were young, inexperienced and naive. Our first project was called YippieMail and it was an email aggregator. Simply put, YippieMail could display all your webmail accounts (i.e. Hotmail, Yahoo and Gmail etc) in the same web interface (this was before most email providers supported IMAP, so you couldn’t use an email client). Looking back at it, YippieMail was a pretty stupid idea, but it did land us meetings with Sequoia Capital and few other VCs on Sand Hill Road. Keep in mind that this was around the time Meebo raised many millions from Sequia and DFJ to do the same thing but for Instant Messaging (IM), so at the time it probably did not seem as such of a bad idea.

It was in the early days of YippieMail, which was pivoted into YippieMove (RIP 2008-2019) my now decade-long remote experience began (some of which as a digital nomad).

When we began working on YippieMail, Alex was living in San Jose, and I was living in Mountain View. For those of you not familiar with the Bay Area, these two cities are not very far apart, but when you factor in the horrendous traffic conditions, it can easily take well over an hour to drive between the two (while it might only take 20-30 minutes without traffic). It was then we decided to work remotely rather than getting an office somewhere in between. Ever since, in all our subsequent ventures (Blotter, and then Screenly) have been remote-only.

To this day, even though both Alex and I both live in London, we only get together every other month or so in person to catch up. Moreover, in my new venture (WoTT), we have adopted this remote philosophy even if both founders are located in London.

So what have I learned over this decade of working and running remote teams? Let’s dive in.

Remote is not for everyone

The first thing that I would like to point out is that remote working is not for everyone. Over the years, we have had a few team members that could not work remotely. In some cases these people discovered this themselves and chose to leave, and in some other cases it became clear that it was not a match.

Usually, people who fail at remote work tend to either lack the self-discipline it requires, or they are simply socially oriented and thrive being around other people. In the latter case, working from a shared office can help, but even then, if you lack the self-discipline and habits required, you are likely not going to thrive. While there are plenty of exceptions to this rule, young people (early 20s) tend to struggle more with this than people who have reach their late 20s and early 30s.

The bottom line is that some people excel while working remotely, while others work better in a regular office environment. It’s hard to screen for this in an interview, but it usually becomes evident during the first year. It is important to look out for this in team members as a manager.

Either you’re remote or you’re not

Either you’re remote-only or you don’t do remote at all. Lots of companies brag about giving their staff the freedom to work remotely. However, the reality is that unless it is in your company’s DNA to be a remote company, it will inevitably favor the team members that are working in the office (in particular if this is where the leadership is). The reason for this is largely related to the flow of information. People chat over the water cooler, over coffee or over drinks after work. This leads to unevenly distributed information, which easily can make people feel left out or that other team members simply assume everyone else knows about something despite it never made it to the official channels. In a remote-only culture however, the information flow tends to happen in a more organized fashion either over email or in the company chat rooms (or even in Github Issues).

Company and team summits

Company summits matter a lot. Even if you’re a remote team, having everyone get together in person every year (or twice a year) can make a huge difference. While video chats is a higher context medium than email or chat, it still isn’t a full substitute for meeting face-to-face. When we did our very first summit for Screenly at the lovely Villa Lava in Croatia (a great place for company summits), it was the first time our team members got to meet each other in person, despite having worked together for years. In retrospect, it was a big mistake to not be doing summits earlier, as we could see a big difference in how the communication changed online after the summit. Because text based chat is a low context medium, it’s very easy to misread the intent of a message. However, if you have met this person in real life, you have a lot more to work with and can use that context to read the same message in a new light. These days, the developers at Screenly get together in person every quarter (roughly) for a one week summit, and the entire company gets together annually. (You can read more about how we work at Screenly in the article How we work at Screenly that I wrote a few years ago.)

Tap in to a large talent pool

Hiring remote means a larger talent pool. I’m hardly the first to point this out, but one of the major reasons why it makes sense to be remote-only. You are no longer limited to hiring in your geographic area. The tools for recruiting have changed a lot over the last decade since I started working remotely. That said, recruiting is far from easy. Because people from around the world are able to apply to your openings, the second you post a job ad, the floodgate opens. The reality is that 99.9% of the applicants for remote jobs are people who utilize the “spray and pray” approach. Filtering them out is fairly easy, but in best case scenario, you’ll have a handful of decent candidates for every 100 or so applicants.

The filtering process that tends to work well is to have rigorous screening questions that actually requires a little bit of work and is unique. This will help you weed out all the candidates who simply put “Call me to discuss” in all the boxes (or worse).

Yes, this screening process will take a fair bit of time, but tools like Upwork make it fairly quick to reject candidates that fail to put in the effort (or are clearly poor fits).

From experience I am also very reluctant to work with agencies and prefer hiring team members directly. The reason being that a number of agencies we’ve run across over the years have a small amount of talented engineers that will do the screening process and perhaps the first few weeks, and then they gradually shift the work over to a more junior person, while charging the same rate.

It’s also worth mentioning that with the raise of the digital nomad movement, there are a lot more job boards that are “remote friendly,” including Angelist and a plethora of (IMHO overpriced) remote-focused job boards.

A final word of warning for people hiring remote team members: don’t hire people who want to join your company just because you offer them to work remotely and subsequently have more flexibility. While not always true, it is sometimes an indicator of people who want to coast along with minimal supervision (while perhaps getting their own business off the ground). What you really want is people who believe in the vision and product, and where remote is a perk, not a the reason why they want to join.

(I have intentionally not mentioned the legal structure of how to hire remote talent. IANAL so you probably should check with one to ensure you comply with the local laws.)

Finding good remote workers is probably easier for some roles than others

Remote work is likely easier for engineering than for other roles. In all my experiences, we have always been engineering heavy organizations. Yes, we’ve had a number of other roles too, but in terms of head count, the engineers always outnumbered all other roles. What I have noticed however is that it tends to be easier (in general) to manage engineers remotely compared to other roles (such as sales). This is likely related to a number of variables, but in general, I’ve found engineers to be more self-motivated and requiring less handholding. There is of course a large correlation with seniority too. Regardless of position, more senior people tend to require less handholding and thus work better remotely.

Remote is a major time saver

Remote work saves a lot of time. First, it should be said that remote work does not necessarily equal working from home. We’ve had plenty of team members over the years that preferred to work from a shared office (including myself for a period). To each and their own. If however you work from home, you can save a big chunk of time (and money) every day. When I had an office in Shoreditch, it took me 30-40 minutes each way. That adds up top a lot of time every week. These days I have a dedicated room as my home office (something I strongly recommend if working from home). This means that my morning commute is roughly 60 seconds, and that includes a detour to the kitchen to fetch myself a cup of joe. What you do with this time is up to you, but I usually dedicate this 1-1.5h every day to exercise.

The power of routines and habits

Habits will make or break you as a remote worker. As mentioned earlier, remote work is not for everyone. It requires a lot more self-discipline than a regular office job where you’re constantly “supervised.” Over the years, I’ve experimented with a large number of habits, and at this point I’ve devised a set of habits that work pretty well for me (but they are likely to change as I keep experimenting). The most important habit when working remotely from home is to mentally trigger a beginning and an end of the work day. It’s easy to sit in your PJs or sweats all day just because you can, but it will likely backfire in the long-run.

To make this more concrete, here’s my current daily schedule:

  • 07:00: Wake up
  • 07:05: Reading (Sharpen the saw from The 7 Habits of Highly Effective People)
  • 08:00: Check in with the team
  • 08:10: Exercise + shower
  • 09:30: Start of my work day
  • 19:30: End of my work day
  • 23:00: Bedtime

Clarification: This does not necessarily mean I work 10 hours per day every day (sometimes I do). I do take a lunch as well. Also, I am perfectly happy to wrap my day at 17:30 after a productive and sucessful day. The 19:30 hard stop, not as hard requirement for me to work to it every day.

As my good friend Milos (@milosgajdos) pointed out while reading a draft of this post, an early start isn’t for everyone. Shifting your day is perfectly fine too. The point is not when you start your day and when you wrap it, but building and sticking to habits that make you productive.

If you want to learn more about the importance of habits, I strongly recommend reading The Power of Habit by Charles Duhigg. Also, a word of warning, don’t get obsessed with reading all about productivity. I’ve been a victim of productivity-porn myself, but I can tell you first-hand that you’ll waste far more time reading about it than you’ll ever save.

Sleep matters (shocking, I know…)

Perhaps not related to remote work itself, but more the startup culture. VC used beat it in to young and naive early 20-something kids that it was cool (and even expected) to frequently pull all-nighters and sleep under their desk. I feel like the tide has finally turned on this. Yes, you still have the Gary Vaynerchuk-wannabees out there with their hustle-porn, but I think (and hope) they are a dying breed.

What is however related to remote work is the the importance of wrapping up your day. As you may have noticed above, I end my day at 19:30. After that I’m not allowed into my office (unless there’s an emergency). I also try to keep my screen time to minimal in the evenings. In my younger years, I frequently worked late into the night. Yet, even if I clocked more hours, I got less done.

Switching off very is important, and it is a lot more challenging when you’re working remotely.

If you want to learn more on this, I recommend the book Why We Sleep by Matthew Walker.

Distractions kill productivity

Kill the distractions. Working from home is challenging for a lot of people. It’s easy to get distracted by various things around the house, but for me the biggest distraction has always been the digital kind. Cal Newport nails this in his latest book Digital Minimalism, where he talks about how distracting mobile phones and social media can be. I’ve found this first hand. For a long time, I kept my phone next to me on the desk. However, every time the phone buzzed, I lost my focus. Even if I did not check the phone, it still got me distracted. The remedy for me was to simply move all my distractions to the living room (i.e. my phone and Apple Watch) and just check them periodically throughout the day. Alternatively, Airplane mode on your devices is another great way to kill noise.

For the hackers out there, I’ve found that running something like i3 is also great for cutting out noise on your desktop. I use this on my “developer workstation” (which is different from my other workstation).

Don’t skimp on equipment

While having good equipment is always important, you tend to have more control over your equipment when working remotely than when you work in an office where everything is provided to you on your first day. You are going to spend a lot of time in front of your workstation. Your body will thank you for spending a bit more money and get:

  • A large 4K screen (they have crawled down a lot in price recently) on a monitor arm
  • A standing desk (I use this one from Ikea)
  • A good ergonomic keyboard

That’s a wrap!

That’s it. At least for now. I’m sure there are things that I have missed, but it should hopefully be useful for other (new and old) remote workers out there.

If you are eager to learn more, I would recommend the following additional books:

  • Deep Work by Cal Newport
  • ReWork by Jason Fried and David Heinemeier Hansson (DHH)

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