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BrentOzar gives a great answer about financial/legal issues, and sytse gives another great answer about investor risk. I'll add some thoughts from a more "down in the trenches" (and ten-year remote developer) perspective.

First, remote work just isn't for everyone or for every situation. Some people thrive on frequent interaction with others, and just don't have the same energy when they have less. Some get outright depressed. Teaching/mentoring also requires frequent interaction, which is an issue for a team with a lot of new people. Sometimes online interaction is an adequate substitute. Sometimes it's not. Also, some people simply don't focus as well and let themselves get distracted too much when they can't literally see and hear others working around them.

Second, dealing with remote workers requires a change of habits that many find unwelcome. You have to write more and speak less. When you do speak via phone or VC, you have to learn new conversational protocols. Our subconscious protocols for when it's OK to start speaking and when to listen tend to break down a bit especially with high delay or poor connection quality, so people have to work a bit to make sure everyone gets their say.

Anyone who works remotely also has to be hyper-aware of time zones. If folks on the US west coast never want to meet before lunch, it's going to cause friction with people on the east coast who would rather not have meetings after 5pm almost every day. Similarly, if those west-coasters like to do solo work at the beginning of the day and collaborative work at the end (a common pattern for reasons I don't fully understand) they're going to hit that full-day round trip latency for questions and code reviews more often. And that's all with only a three-hour difference. In general, it gets even worse when larger differences are involved.

I've been working remotely for a decade. It works for me largely because of how I am and because I very actively try to teach my colleagues about how to make it work. Sometimes it barely works, and I wouldn't count on it working for a different person or a different team/project.



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