A bunch of articles and blogs have been written about working from home, but I was recently asked for my take on remote work challenges, so here’s yet one more. To give a little context, I worked from home 50% from 2012 to 2016 with my team spanning the range from 100% in-office to 100% remote. From 2016 to 2018, I was 100% remote with my entire team also 100% remote.

Flexibility Flexibility is the #1 perk of remote work, how can it be a challenge? People are creatures of habit. When all of a sudden you don’t have to get up in the morning, shower, eat, drive to work, then sit at your desk, your brain can get a bit confused about what it’s supposed to be doing.

The best thing I’ve found is to keep a schedule and actively stay a presentable member of society. Keep your working hours consistent, shower and dress presentably every day, and go out into the world in the evenings. For example, when I’m living office life I have groceries delivered, but when I’m primarily WFH, I go to the grocery store IRL.
Focus While you’re not as likely to be distracted by drive-bys or office chatter while working from home, there’s a whole host of non-work-related things that will by vying for your attention: kids, pets, Netflix, housekeeping, and noises outside for a start. Work from home long enough and you’ll know every delivery truck schedule and how often each of your neighbors mow their lawn.

The biggest help here is to make sure you have a dedicated office space (preferably with a door that closes) and a highly functional, non-cluttered workstation. The goal is to avoid non-work things being in your field of vision while you’re “at work”. One of the worst things you can do is trying to WFH on the living room couch or at your workbench where you play with personal projects.
Communication In my experience, communication seems to be the most interesting (or at least SEO-friendly) challenge for remote workers as there are more articles and vendors in this space than any of the others. The long and short of it is that humans send and receive a ton of information IRL and when we reduce the bandwidth of that connection, things can break down.

The best approach I’ve found on this front is to make communication as multi-modal as possible. Use chat, email, tickets, phone calls, video calls, and by all means meet up IRL when the opportunity presents itself. The more disparate interactions you have with someone, the more you’ll naturally get to know them which will improve your understanding no matter what comm channel you’re currently using.
Burnout Losing the commute is one of the absolute best things about WFH. That said, lots of folks use their commute to mentally shift gears between home and work. Getting rid of the commute can lead to a state of perpetually being somewhat at work which burns folks out surprisingly quickly.

The goal here is to have a solid context switch – something that says I’m working now or I’m hanging out at home now. For me, the most effective thing is to have a dedicated work laptop and a dedicated personal laptop. I never, ever work from my personal machine and I never, ever do personal stuff on my work machine. When I start my workday, the personal machine gets undocked, closed, and set off to the side while the work machine goes into the dock. At the end of the workday, the process is reversed. If the machines are running the same OS, I also make sure I’m using different desktop backgrounds, themes, etc. Context is everything.
Tribal Knowledge One of the best things about working in an office is that after a few months, you magically know a lot of stuff. You get to know people casually even if you don’t generally professionally interact with them. You overhear things in the hallways. You see who visits who’s office. You see prototypes if you happen to work inside a secure zone. If you’re particularly unlucky, you hear one side of every sales call the company makes. You lose most of this by being remote.

There are a few things you can do to improve the situation, however. One of the easiest is having non-work channels on the company chat. Giving people the opportunity to chat about dogs or cars or cooking or whatever it is that they’re interested in helps to build those connections.

Another major help is simply writing things down without making it too formal. Wikis and Slack logs can make for excellent “collective memory”. One perk of this approach is that through RBAC you can actively manage where different organizations have shared history vs encouraging unique/specialized perspectives.

Finally, my favorite approach is to have a few people who straddle the line between office life and WFH. These folks tend to pick up tribal knowledge while they’re in the office, then share it over remote channels with everyone else. Maybe I just like this approach because I enjoy straddling this line myself. =)