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Holloway Guide ToRemote Work

Improve the way you work together—even when you’re apart.

A comprehensive Guide to building, managing, and adapting to working with distributed teams.

  • The 330+ page Guide
  • Curated commentary from experts
  • Ongoing updates to the content
  • PDF copy for offline reading that’s yours to keep
  • Access to advanced search, bookmarking, and other features on the Holloway Reader
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Everyone has written a guide on remote work—but no one has done so as diligently and comprehensively as Holloway. They’ve spoken to everyone who knows about remote work, and do not shy away from what’s tough or complex.Job van der Voort(CEO, Remote)
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Everyone should have access to expert knowledge.

Companies are increasingly struggling to afford office space and hire and pay talented employees in expensive cities. More and more, employees want flexibility and choice in their work—to be near family, to be rid of time-consuming commutes, to have lower costs of living. These operating costs and hiring pressures—paired with an explosion of in-home broadband access, smart phones, and cloud-based tools—make remote work an intriguing option for a growing number of companies. But anyone who has spent enough time working remotely knows that it is an ongoing and dynamic series of tradeoffs for everyone involved.

Luckily, the people contributing to this guide have been involved in remote work for over a decade. We’ve been at large companies with work-from-home policies, hybrid companies navigating the complex interactions of offices and remote employees, to all-remote startups that don’t have any offices. We’ve seen how remote work can unblock hiring obstacles, save money, and provide employees with more satisfying, meaningful, and healthy careers. We’ve also seen dysfunctions in nearly every domain, from treating remote work as a privilege for a select set of people, to isolated, burnt-out workers left to their own devices. Those trying to build effective remote teams can benefit from these experiences, and avoid costly mistakes.

The lead authors of this guide, Juan Pablo Buriticá and Katie Womersley, lead large distributed engineering teams at fast-growing startups (Splice and Buffer, respectively). Additional contributors include Andreas Klinger (Angel List), Job van der Voort (Remote.com), Hiten Shah (FYI), Brenna Loury (Doist), Laurel Farrer (Distribute Consulting), and many more. We cover practices at companies like GitLab, Trello, Zapier, and many more, with the goals of helping managers design what works best for their company and employees, and helping employees make the most of their remote experience.

We believe remote work is a viable and important element of modern work that stands to reshape significant aspects of how companies, employees, and economies function. With the right foundations and practice, companies and employees can approach this complex, ever-changing landscape with knowledge and confidence.

Does this sound like you?

  • I’m worried my team won’t work well together if they’re not all in the same office.
  • I want to hire someone in another country, and I have no idea what that entails. Where do I start?
  • I’ve heard remote teams have to write everything down. Is that true? How would we get any other work done?
  • I’ve read blog posts saying companies that are entirely remote do better. Should we ditch the office and have the entire company be distributed?
  • How do people handle time-zone differences in remote teams?
  • What tools do remote teams use for tracking projects or collaborating?

Table of Contents

Part I
Remote Work Benefits
Remote Work Myths and Pitfalls
Practices of Successful Remote Teams
Remote Company Culture
Part II
Working Together When Apart
Key Channels and Tools for Remote Communication
Remote Collaboration Ground Rules
Staying Aligned Across Remote Teams
Remote Team Agreements and Protocols
Making Decisions Remotely
Remote Meetings
Handling Urgent Issues Across Remote Teams
Part III
Managing Distributed Teams
Compensation for Remote Employees
Onboarding Remote Employees
Remote Team Integration
Remote One-on-One Meetings
Goal Setting and Feedback for Remote Teams
Morale, Mental Health, and Burnout in Remote Teams
Sharing Difficult News with Remote Teams
Part IV
Being A Successful Remote Worker
Key Strategies for Remote Working
Skills for Successful Remote Work
Setting Up Your Remote Office
Being Professional When Working From Home
Personal Health for Remote Workers
Part V
Legal, Tax, and Operational Concerns
Hiring Remote International Employees
We all have opinions and thoughts on how to effectively work remotely, but no one blog post or medium article offers the complete picture. The Holloway Guide to Remote Work expertly synthesizes the state of remote work from hundreds of interviews, conversations, blogs, and research so that we all can make the right choices for ourselves and our companies.Scott Hanselman(Partner Program Manager, Microsoft)

Researched, written, and edited by experts.

Written by practitioners. Edited by professionals.

Lead Authors
Katie Womersley (Buffer)
Juan Pablo Buriticá (Stripe)
Contributing Authors
Haley S. Anderson (Just Security)
Paul Maplesden
Paul Millerd (Boundless)
Courtney Nash (Holloway)
Steph Smith (Integral Labs)
Contribution and Review
Greg Caplan (Remote Year)
Toni Cowan-Brown (Protocol)
Matthew Damm (Fenwick & West)
Ryn Daniels (HashiCorp)
Stephan Dohrn (Inside Out Coaching)
Rodolphe Dutel (Remotive.io)
Ben Erez
Laurel Farrer (Distribute Consulting)
Joe Giglio (Chief Remote Officer)
Bud Hennekes (A Boundless World)
Andreas Klinger (AngelList)
Morgan Legge (Convert)
Brenna Loury (Doist)
Darren Murph (GitLab)
Kristen Pavle (Ponder)
Dan Pupius (Range)
Hiten Shah (FYI)
Jonathan Siddharth (Turing)
Dave Smith (Packet)
Kevin Stewart
Luke Thomas (Friday)
Job van der Voort (Remote.com)
Kathleen Vignos (Twitter)
Judy Williams (The New Stack)
Jay Yuan (Turing)
Additional Thanks
Sophia Bernazzani (Owl Labs)
Darren Buckner (WorkFrom)
Frank Chen (Slack)
Matthew Gregory (Ockam.io)
Jody Grunden (Summit CPA Group)
Nathaniel Hemminger
Liam Martin (Running Remote)
Lauren Moon (Atlassian)
Jeff Morris, Jr. (Lambda School)
Oliver Starr (Turing)
Anita Umesh
Editorial and Production
Courtney NashLead Editor
Rachel AndrewEditor
Carly GillisEditor
Hope HackettSwiss Army Knife
Vahe HovhannisyanGraphics
Rachel JepsenEditor
Joshua LevyDesign
J. Marlow SchamauderCopyeditor
Titus WormerPrint Engineering

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  • The 330+ page Guide
  • Curated commentary from experts
  • Ongoing updates to the content
  • PDF copy for offline reading that’s yours to keep
  • Access to advanced search, bookmarking, and other features on the Holloway Reader

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We believe the reading experience for book-length resources can go beyond paper or e-books. Reading on Holloway means a distraction-free, interactive format to help you find what you need, when you need it, in your browser. Digital access to a Guide also means access to ongoing new content, curated commentary from experts and readers, and features like search and bookmarks.

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Over 90 definitions of key terms

Psychological safety is a shared belief held by members of a team that the team is safe for risk-taking.* Psychological safety enables team members to express new ideas or suggest improvements or changes without fearing potential negative consequences. As a result, psychologically safe teams take more risks and perform better. Unlike trust, which focuses on how individuals feel about each other, psychological safety is focused on beliefs about group norms, and being respected within the group.

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Pitfalls and confusions highlighted

dangerWhen thinking about remote work, both startups and larger companies often look to other, often famous, companies for inspiration. But you are (probably) not GitLab or Basecamp, and “just use the GitLab handbook” can be inappropriate advice. The approach to remote work that you want is not necessarily the same. Each company’s size, growth, philosophies, and financial outlook may be very different from those of other companies. And if you’re an employee, one company’s handbook or philosophy won’t necessarily help you succeed elsewhere. We can learn a lot from seemingly successful remote companies, but we shouldn’t blindly copy them.

confusionTerminology about remote work is fraught with debate and inconsistency. Despite the fact that there’s a growing movement behind using the term distributed over remote—notably, viewing team members as remote can have hierarchical implications about what is “central” and what is not—for the purposes of this guide we will use “remote work” throughout to refer to the broad category, and draw distinctions about fully distributed companies or teams when relevant.

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This guide is an epic undertaking. It’s an incredibly comprehensive look at all aspects of work as they pertain to distributed teams.Daniel Pupius(founder, Range)

Why pay for a Guide?

At Holloway, we imagine a place on the web where depth, quality, and high-value writing are the norm. A place where experts’ ideas are accessible to anyone. Where thoughtful, inclusive, and well-written resources win over quick takes, self-promoting blog posts, and content marketing.

We believe you, the reader, know the difference. It’s 2020. You recognize sites riddled with ads and clickbait headlines. Deep and comprehensive resources take expertise, time, and money to build. By buying access to a Guide, you’re supporting a place online that makes longform reading a pleasure—and allowing us to pay authors, contributors, engineers, and editors who build and improve them. We see Holloway as a new and powerful way to publish. We hope you’ll join us on the journey.


This is the best guide I’ve seen on what shifting to remote work really means. The comprehensive collection of insights, best practices, and expert knowledge is not only deep, but easy to navigate in the Holloway format. I hope this guide inspires companies to explore remote work from a deeper perspective, and use it as a way to unleash human potential in the organizations of the future.Paul Millerd(entrepreneur and consultant)
When it comes to remote work, most of what you find online is anecdotal or individual points of view. Holloway assembled an incredible team with a lot of experience to consolidate ideas and create a shared understanding of the challenges and the methods of working remotely. Starting with a first-principles approach around work, culture, and communication, the guide evolves to practical guidance and curated benchmarks for individuals, teams, and companies.Raphael Straatmann(co-founder and CTO, Liv Up)
Characteristically comprehensive, manageable, and enjoyable, this new remote work book feels both timely and futuristic. Unless you play in the NBA or are raising a barn, you’ve been working more or less remotely for decades—at your desk, in an office, connected to others through a variety of devices. Not being physically present with your coworkers is a natural continuation of this trend. This book is Holloway’s most ambitiously self-fulfilling to date: we will soon look back at it and wonder how this wasn’t always perfectly obvious to our old selves!Anna Gát(founder and CEO, Interintellect)
Many organizations and teams are suddenly finding themselves forced to implement emergency remote work policies, but that doesn’t mean those big changes need to be handled sloppily. The Holloway Guide to Remote Work is a super well-structured, one-stop shop for everything you need to think about when attempting to transform a culture to support healthy remote work. Plus it’s a pleasure to read!Buster Benson(author, Why Are We Yelling? The Art of Productive Disagreement)
Data-driven yet human-centered, this is a comprehensive, thoughtful, and brutally honest guide to remote work. Hiring, onboarding, meetings, mental health—the Holloway Guide to Remote Work has it all.Anne-Laure Le Cunff(founder, Ness Labs)
If you really want a deep dive on the ins and outs and how-tos and oh-no!s of remote, this is by far the best thing out there. You can go from learning to help prevent burnout in your teams to the legal and tax implications of hiring global workers, all in one place. It’s truly remarkable.Greg Caplan(CEO, Remote Year)
The current pandemic has turned a lot of people on to remote work by necessity, and there’s a ton of stuff coming out every day to try and address the current upswing in information requests. A lot of it is just corporate marketing. This is not that. Holloway’s been working on this guide for months—it’s comprehensive, has a ton of contribution from people with all kinds of experience in remote management, and the format makes it easy to navigate to the problem you’re having right now.Andreas Klinger(Head of Remote, AngelList)
The most important aspect of a remote work strategy is to be intentional about it. This guide will get you thinking about which best practices apply to your business.Hunter Walk(Partner, Homebrew VC)
The biggest mistake a manager of remote teams can make is doing too much of the wrong thing, and not enough of the right thing. The wrong thing is micromanaging because you can’t see your team. The right thing is documenting everything so that you don’t have to see them. This guide not only explains why one is better than the other, but exactly how to do it successfully. Gold.James Turnbull(VP of Engineering, Glitch)
Such a complete guide to remote work was long overdue. More often than not, remote work has been studied and written about through a very tech-centric lens. Holloway’s guide provides an in-depth look at how everyone can adopt this new work style.Toni Cowan-Brown(Director, Protocol Media)
Distributed work is hard, but the benefits are incredible when you get it right. I can’t recommend this insanely comprehensive guide highly enough.Nathan Baschez(founder and author, Divinations)
People often ask me what tools we use to manage our distributed team at Product Hunt. Unfortunately you can’t simply install a few apps to run a remote team efficiently. Remote working is an intentional approach to communication that is fundamentally different from traditional office work. It requires trust and effective asynchronous communication. The Holloway Guide to Remote Work is a useful resource (alongside those tools!) to become a strong remote teammate or leader. I’m glad to see more knowledge being shared on this topic.Ryan Hoover(founder, Product Hunt)
This guide is a comprehensive resource of start-to-finish advice from the world’s top remote work experts. It’s a game changer for the future of virtual jobs.Laurel Farrer(founder and CEO, Distribute Consulting)
Companies exploring remote work, take notice! This guide covers what you need to know to get started and succeed, remotely.Rodolphe Dutel(founder, Remotive.io)
If you work remotely in any capacity, this guide is a no-brainer and will pay for itself in a week. There’s no need to reinvent the wheel—it provides a playbook for making remote work, work.Luke Thomas(founder and CEO, Friday)
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