I've worked remotely for almost seven years, for companies of many shapes and sizes (ranging from 7 to 150+). I've been a part of early stage companies, to well established organizations. I guess you can say I've been able to collect quite a few data points on how to work on a distributed team: I've also learned what NOT to do as well.
If you're curious, I've written a few posts on remote work that you might enjoy:
I've read many of the books on remote work that exist and the unfortunate reality is that most of them are terrible.
The issues I have with the existing books fall into a few themes:
With that being said, there's a few good book picks I'd like to share below. I'll also mention books that I think are worth avoiding (there's a few that have great reviews on Amazon, but in reality, are mediocre).
Okay - let's jump into the best remote books I've read. This list is updated and highlights the best books as of January 2021.
We are writing our own book on this topic, called the Anywhere Operating System. Unlike the other books mentioned, this book is written for a post Covid-19 world. Instead of trying to convince you that working from anywhere is the future, instead, we are focused on helping you navigate these changes with a user manual.
The book is segmented into two parts:
The first book recommendation is Remote: Office Not Required, by Jason Fried and David Heinemeier Hansson. This is probably the best book I've read on convincing your boss to let you work remotely. With that being said, you shouldn't expect to gather rich, tactical insights here. One Amazon reviewer hit the nail on the head with this review:
"I felt this book was better suited for companies/mangers that are on the fence about remote work vs. companies like mine that have already embraced it. As the owner of a company with a remote workforce, I don't need to be convinced about its benefits, I need more help with the everyday challenges that come a remote workforce."
If you're looking for tactical advice on how to work on a distributed team, you won't find too much of it in this book. With that being said, there's advice on collaborating on a remote team - like how important timezone overlap is. Additionally, the authors discuss one of the most important topics (in my view) - cabin fever and loneliness.
Overall, I recommend this book as a way to build a healthy mindset around working remotely (or to convince your boss to let you work remote).
My second book recommendation is The Year Without Pants, by Scott Berkun. This book takes a different tone compared to Remote; it is a personal story about Scott's year working remotely at Automattic (one of the largest fully distributed companies out there).
As the title suggests, the book is a humorous read, although some of the topics may be specific to one company vs. being practical advice that you can use. Additionally, this book was written in 2013, so there's some outdated tools and processes that have been mitigated with recent technology like Slack or Zoom.
My favorite chapter was called, "Your Meetings Will Be Typed"; in this chapter Berkun discusses various tools and processes they used to communicate (including a tool called P2). I'd argue communication is the most important thing remote teams need to get right, so it's good to see people covering it in a bit of detail.
To date, this is the most comprehensive, tactical, and up-to-date guide you will find on remote work. The best part is that it's free. What I like about this book is that it shares stories from a first-hand perspective (Zapier is a 200-person fully distributed company), but the advice is stuff that you can apply to your team/organization.
My favorite "chapters" in this book are:
Overall, this is a must-read. It balances out the other book recommendations with tactical, yet helpful and applicable advice.
Unlike the other book recommendations, Distributed Work is written from an academic perspective in the early 2000s. While this book is extremely dense and research heavy, it also contains incredible insights on the topic. This is a deep, deep dive into the topic of distributed teams.
Some of the problems with remote work outlined by the author have been mitigated over time thanks to technology, but some of the problems mentioned nearly twenty years ago are still very real.
If you want to build a foundation for "why", this is a MUST read...just don't expect to read the entire book in an evening (it's ~ 400 pages). I'd love to see this book be updated for the modern workplace.
This is my favorite book on the topic due to how deep it goes.
This next book recommendation isn't specifically about working remotely, but it's very relevant to life as a distributed employee. Deep Work, by Cal Newport is a wonderful book that discusses the important of uninterrupted, focused time to produce a high-quality product. Remote work is ideal for this.
The modern workplace is filled with distractions (i.e. - open office floor plans) that prevent you from doing your best work. This book dives into how you can take back control of your day and get more done.
The book is segmented into two different sections:
My favorite section was a chapter called, "Work Deeply" in which the author discusses how important rituals are. At Friday, we've built software to create communication rituals at work.
Finally, I'd like to quickly share books that I do NOT recommend reading. The only reason I'm mentioning these books is because they have strong Amazon reviews (so I purchased them), but was sorely disappointed.
Again, this is my personal preference. You may find value in them. I did not.
I feel like there's an opportunity to create a book that dives into the foundational elements of working on a distributed team (not generic advice), but doesn't read like a textbook. That's why I've decided to write my own book on distributed work. If you'd like to follow along, I'd love your support!