Solid post — as someone who’s worked remotely for almost 8 years (and is building software for remote teams), the categories ring true.

I’d argue that these challenges are primarily based around communication (or the lack thereof). Feeling isolated at work is a communication challenge, being disconnected is a communication challenge, and watercooler serendipity is a communication challenge.

I’ve found that media richness theory (http://campus-adr.net/ODRModule/media_richness_theory.html) presents an incredible way to frame these challenges around remote work. Specifically, the remote worker needs to rely on “lean media” a lot (written communication, Slack, etc), while the person in the office can spend a lot of their time in a media-rich environment (like in-person meetings + watercooler discussion).

If an organization wants to make remote work better, then need to adapt communication to the “channel” that makes the most sense. For example:

• information sharing (like status update meetings) should be done asynchronously and in a written format as there’s not a lot of ambiguity.
• For collaboration and a lot of back-and-forth, you need to be on a video call (or fly to the office). Otherwise, misunderstandings will 100% happen.

The best companies understand this and build regularly occurring communication habits at a team and company level.