How does one run an organization remotely, effectively?

I haven't been able to personally try or validate much from the book. It's more that the things in the book make a lot of sense to me, and that I have a good amount of trust in the authors.

That said, there are some things that I do have personal experience with and can contribute my data point. I just started an actual remote job three weeks ago, and before that I've spent years as a solo founder of a startup, and autodidacting.

• The biggest thing (by far?) I've encountered is that it's important to have an off switch. Working from home, it can be tempting to check in and do a few tasks at 10pm. But when I do that, it makes it hard for my mind to properly "shut off" and relax.
• I've found cabin fever to be a minor issue when I stay home too much, but never a major one.
• I don't feel like I can get away with slacking off at home. I feel like I'm ultimately just being judged on my output, the same as it is in a physical job. At the end of the day if my output isn't there, I feel like my job would be at risk.
• At the job I'm currently at we do something called donuts where every two weeks we're paired with someone on the team to have a video chat with to get to know each other, and where talking about work is off-limits. The donut call I had made me feel closer to the people on the call, but I've also started to feel closer with the people I've been interacting with in general. And it's not clear to me that feeling closer to people translates to more productivity at all.
• Some people on my team aren't native english speakers and have trouble with writing, but despite that, I don't think it actually is much of a barrier. It involves a little bit more back and forth, but soon enough the signal comes through. This goes against one of the chapters in Remote. Perhaps being a clear thinker is what is important versus being a clear writer.

Okay. From a practical point, one thing I've found is working remotely from the office introduces two immediate challenges.

First is the loss of the informal information flow -- the remote person just quickly drops out of the loop. When the whole team suddenly becomes becomes remote that informal information flow is just gone. New communication patterns might help mitigate that. I now one of the clients I used to work with had a policy that all emails related to work got sent to everyone. That might not be what you need but they strongly felt that insured the corporate distributed knowledge was preserved and in some cases extended -- sometimes really good insights came from people not directly working on a particular project; sometimes brand new opportunities were seen because multiple teams notices some common threads.

Avoiding the pressure to micromanage will likely be important. Clear goals statements, progress milestones and probably some good mechanism to raise a hand to point up an emerging problem.

When people get moved from the office to working remotely you will likely find that there were all sorts of things taken for granted that made one more productive -- or just made the work easier. Before cutting ties with the office everyone should closely survey their remote work environment to make sure they can do the job remotely as well as in the office from pure procedure steps. Do I really have sufficient desk space or am I trying to work off the kitchen table? With the table work -- is the light right? Too many distractions maybe? What about things like screen space? Access to applications remotely -- does the VPN really kill the connection so you know it will take twice as long to get results back?

If the organization doesn't already have experience with operating on a remote basis it really needs a few dry runs to learn what it doesn't know. So will be the people. Does the organization have time to do that?

Contact lists -- yes, everyone has the office directory but that might not be too helpful when everyone is not remote. Does the phone system support call forwarding -- and does that functionality expose the number the call is then forwarded to. Is that a problem? How well will everyone work if all they have is a cell phone. What's the backup plan there -- online tools (Skype, Zoom, MS Teams or other tools might be good but also might be problematic based on various security setting or bandwidth to the remote location (I am guessing home -- so another twist there is who else is in the house? Does everyone have a work space or will people be trying to work out of their bedrooms in a shared house?)

Most of that is mostly mechanical aspects.

One of the soft aspects is loss of vision -- people cannot monitor each other as they do in the office. That will probably lead to some tension over (not too much) time. It's natural for most of us to see the work we do and see the work not done by others we needed them to do. (I think there have been so posts on LW in that vein of thinking). That's part of a culture shift moving for the co-located office to everyone remote. How best to minimize that type of dynamic should be considered. Maybe some type of group conference call where everyone can share experiences, what's working and what is challenging might help keep everyone feeling they are all in the same boat with one another and not a case of multilateral "me-them" feelings.

These are they types of things I've see or experienced.

If you are thinking about your own organization my suggestion would be some trial runs. The organization was not setup initially for the remote structure so unlikely to have what is needed to support that. There will be a learning curve.

In terms of how to manage the output and make sure the organizational output keeps getting produced you probably already have most of that. They might be a few things you can think about the are directly observed during the normal course of the day. If they are really important from a "run the company" view what is the proxy in the remote setting? What is the impact of generating that proxy measure on just getting the job done?