Thoughts on Remote Work

January 22, 2019

I was just commenting on this thread on Twitter and decided to write down the same thoughts more coherently. This is a quick summary of my thoughts on remote work, which is pretty trendy these days.


A few weeks ago I decided to start interviewing people on distributed teams, with the idea that there must be lots of fertile ground for products to be built in this space. It seems obvious that in an online world, the future of work doesn’t require a group of co-workers to be in the same room.


I went into these interviews expecting to find a discrete problem to solve around organization, communication, or logistics. After speaking to about ten remote employees or founders, I didn’t really find any obvious problems of that nature. Instead, I found bigger problems with the nature of remote work.


My overall takeaway: Remote work will be the future, but not until there’s a big change in how it’s done.

The Current Dogma on Remote

If you read blog posts online, or talk to anyone who works remote, they’ll all tell you the same thing: Remote teams require a lot more process. Like five times the process. More communication, more documentation, and more structure.


If you go on to hear about the way they work, you find that most of these teams have solved these problems using a variety of tools. They have documentation systems, asynchronous communication strategies, and task tracking across several tools.


There are many new startups forming right now dedicated to enabling the future of remote work, but I think they’re all missing the bigger vision. If you assume that remote work requires five times the process, what do you build? Things like a knowledge base, a task tracker, a meeting scheduler, etc. Most of these startups are building tools where you can expend five times the effort on process.


And right now, if your team can figure this out, you get all the amazing benefits of remote work. However, I think everyone vastly underestimates how difficult it is to find people who can work this way. I do not think that 80% of people can do it.

Talking to Remote Workers

I talked to about ten remote employees or managers. Each person had figured out a process for staying on top of their work remotely, and each process required someone extremely organized to make it work.


Additionally, everyone I spoke to seemed like an outlier in terms of motivation. They were particularly diligent and had strong internal drive. Each of them talked about the discipline required to sit down and do a full day of work on their own. Even amongst them, almost everyone mentioned feeling at least a little lonely.


Even though I was expecting to find a lot of logistical problems, these companies seemed to have a process that worked pretty well for them. However, it isn’t one that will scale to be possible for all people. I don’t think it’s the future of work.

Unlocking Remote Work for Everyone

I think the defining companies in this space will challenge the assumptions of most of today’s remote teams.


In the big picture, the assumption today is that a remote team requires five times the process. For remote work to be the future, I’d challenge that assumption. Five times the process is too hard for most people.


So, how do you make remote work not require five times more process than being co-located? The simple answer is make it as close as possible to being co-located.

The tools to build that enable the future of remote work will run counter to the beliefs about remote work today. Specifically that will mean:

  • Enable synchronous communication over asynchronous communication
  • Work the same or overlapping hours with your team, instead of whenever you want
  • Don’t work in a room by yourself

The Point

There’s a way of working on distributed teams that works today, but it won’t work for all people. That’s because we’ve only solved the easy parts of the problem and not the hard ones.


We will figure out all the organizational and productivity problems. The hardest challenge of remote work is trying to change fundamental human nature: we’re social creatures, we communicate synchronously, and self-discipline is hard.


Whichever companies can enable us to solve those problems instead of trying to change human nature will unlock the future of remote work.


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