Remote

Quick, work remote! A guide on how to set up your remote working strategy

20 minute read

Today it’s the Coronavirus (COVID-19) pandemic, tomorrow might be another kind of emergency. The result is that many people have been asked to stay at home. Given in the last decade we have now built a fairly effective infrastructure that allows remote working, “stay at home” has now evolved in “work from home” — and its matching hashtag #wfh.

The problem with this is how sudden it is. To go from a local company to a remote company takes time, and having so little time to prepare often leads to experience only the worse sides of remote working. Knowing how to prepare however can make a huge difference in the outcome, to the point that the entire company might also learn in the long term that remote working works, and works well.

The preparations mentioned in this document apply in many scenarios: can be an emergency, can be temporary remote work for other reasons, can be the start of a long-term change in the company. The practices to start remote working are the same.

An important premise that applies to everything: the cultural change that needs to happen is that the company should start thinking of being distributed — 100% remote — even if there’s the expectation an office somewhere. This is a useful rule of thumb: if something is harder to do when remote, it should be fixed.

This article — borrowing from my experience, especially at Automattic — is divided in two parts. One for the company side, one from the individual side. Each section contains a mix of practices, how-tos, tips and how to manage fears. 

The company side of remote

Let’s imagine the scenario where the company has decided to go fully remote, at least in a few offices or countries, for some weeks or longer.

Setup Checklist

How can we make sure we can have people working from home?

For a modern business, usually “going remote” can feel like a radical disruption of how the company works and delivers value, but a lot of digital tools have already made their way during the last 4-5 years showing that it actually won’t change that much. For this reason many companies are already on the verge of being “remote ready”: the change in these scenarios is not structural, it’s often more a matter of culture and policies.

To be sure however, this is the checklist we would go through:

  1. Ensure there’s one synchronous communication tool — people need a way to talk and clarify things quickly, in real-time, when everyone is there at the same time. The scenario this tool covers is: I’ve a quick question or clarification and I need someone for five minutes right now. Example of tools: Slack, Microsoft Teams, Discord, Hangout Chats, Skype, etc.
  2. Ensure there’s one asynchronous communication tool — this is the keystone of effective remote working, a communication tool that allows to write more structured content, usually published somewhere inverse chronologically. It’s substantially a blog or an activity stream. This allows for structured discussions, timezone efficiency, and overall more in-depth discussion. This should also be the main tool for decision making. Example of tools: Basecamp, WordPress, Yammer, Workplace from Facebook, etc.
  3. Ensure there’s one storage communication tool — this might not be strictly needed in the short term, but to ensure success in the long term it’s a very important space to have: somewhere to store things in the long term. Larger organizations likely already have something like this for all company-wide policies and division guidelines. It’s basically a wiki of some form that allows content to be written and searched long term, and it compensates for the first two where time tends to make discussions fall back. Example of tools: Confluence, GitHub, Dropbox Paper, Google Drive, Notion, etc.
  4. Have a video conferencing tool — while many synchronous communication tools provide this out of the box, in some scenarios might be necessary to provide a separate one. Example of tools: Zoom, Hangouts Meet, Skype, Pexip, Whereby, etc.
  5. Make a list of all the company-related activities that happen in person — this can depend a lot on the business, and in some cases might not even be a long list. It however provides the foundation to make sure remote work is successful. Write the list, prioritize it, and make sure that all the activities have a way to be done remotely. Guidelines might be written for each item on the list that provides easy information to people on how to get started. The main thing we expect to be in every list: meetings.
  6. Review security policies — some policies might have been written years ago before even the company got “digital”, and without revisions might force very difficult situations for remote work, or even block it entirely. Revising these policies would benefit not just in the short term, but also in the long term.

If you want to read more in-depth about communication tools, you can check the three speeds of collaboration model here.

Ahead-of-time IT

Will everything work smoothly for employees working from home?

A lot of organizations tend to have too-strict IT practices that disallow employees to effectively access resources from home. It might not be your case, but for this reason it’s important to have the IT department (or whichever part of your organization deals with access control for your systems) prepare in advance. 

It’s difficult to give guidance here due to the large variety of companies and systems out there, but one technique is usually effective regardless of the specific details of your organization: have the people in charge of the company systems to work from home first. That’s one of the most effective ways to identify and fix the issues that might arise, and they are also the most technically savvy people to fix it.

From Meetings to Calls

How can we translate our approach to in-person meetings to running them on calls?

The first activity usually being impacted is “meetings”. The first rule of thumb for these meetings is: can this be an asynchronous activity instead? Would collaboratively writing a shared document work better? In short, can you kill this meeting?

If not, if the meeting is absolutely essential, then it needs to shift to a voice or video call of some form. Your company might have already a video conferencing system in place, so the only thing that should be ensured is that everyone has access (and there are enough licenses).

If you don’t have a company-wide choice already you can explore alternatives: Zoom, Slack Video, Skype, etc. See which one works best.

Notice that you often might want to supplement video calls with a shared document of some kind. A Google Doc or Dropbox Paper that is live edited by everyone can work, but also a shared whiteboard tool like Miro could be excellent.

On the human side, it’s usually advisable that everyone in the call has their webcam on, as it helps countering the detachment of a remote call. However, it’s also important to not make people feel pressured to have the camera on. A camera off might work well for some people, maybe due to the space they are working in, or maybe for neurodiversity reasons. Don’t create a culture that blames people if they prefer having the camera off.

Allowances: Workspace and Internet

What can we provide, as a company, to make sure people are effective in working from home?

It’s important to provide a budget for allowances to give people working from home. While ideally this should be a long-term allowance available to everyone, might also be an exception in the short term.

The amount of this benefit might change from company to company, but here are things you might want to consider:

  1. Internet costs
  2. Babysitting costs
  3. Chair and desk costs
  4. Desk light or webcam light (like this)
  5. Webcam
  6. Headset with microphone (like the Sennheiser SC 30)

While we tried to rank by priority, the importance of each of these can vary from company to company. For example some companies work on high-bandwidth data from local servers (video companies, game companies, …). Providing a top-speed internet for remote workers is a prime need.

Tasks and Project Management 

Do we need to change how tasks are assigned and work is organized?

If you use your office to manage your project, like a kanban board on the wall, this is something that needs to become digital. Luckily, there are already plenty of tools out there that can help: GitHub, Trello, Asana, Pivotal Tracker, Jira, etc. Hopefully your company already uses one of these tools, so people will need to adapt their practice to use them in a slightly different way.

In an office there’s also often the habit of walking to someone to ask them to do something. While this intuitively becomes now a message in the team channel (hopefully not a private message for transparency), it could be ideal to take the chance to think of using one of the digital tools above to explicitly manage these informal tasks too.

Remote Feedback Inbox

How can we make sure we aren’t missing anything important?

Someone inside the company — ideally HR — should prepare a form or other tool where people can submit feedback on things that aren’t working remotely, and then prioritize them and fix them. This should be very transparent and open, and for each issue it’s important that there’s always a follow-up of some kind.

A very simple way to do this is to use a tool like Google Form or Crowdsignal, get all the entries daily in a spreadsheet, and review them all at least weekly to address them. Likely this will peak at the beginning and decrease over time, and it will give visibility to all the issues that people are having remotely — and provide a way for the company to fix them.

Management Fears

How can we ensure productivity when collaborators work from home?

One of the major reasons for companies to not allow remote work is that management fears people won’t work if they are at home. From a pure management perspective, this is a major issue for at least two reasons: one is lack of trust that will make the employee feel bad regardless of how good they are, and two is measuring the wrong thing: the time spent into the office instead of the outcomes of work.

These fears are largely linked to the company culture, and while there are some exceptions they usually correlate to bad management or micro-managers. This isn’t something that can be addressed in a quick transition to remote work, however, it’s also important to acknowledge they exist and they need to be addressed.

One approach could be to open a discussion, possibly even anonymous in a first round before going open, on what are the fears in this regard. Once this data is in, it’s possible to start tackling it in many ways: management training, change of processes, change of policies, etc.

It can help to allow tasks to become more transparent. If managers start making use of a combination of personal messaging and task assignment on open and shared tools (like the project management tools mentioned above) that transparency might be able to ease the fears of the individuals.

The individual side of remote

The company has asked you to work remotely. Maybe you’ve done it before, maybe not, but this time it’s going to be for some extended amount of time. 

Setup your Workspace

How can I set up a specific part of my house for work?

Behavioural economics demonstrates how our environment shapes our behaviours. When it comes to remote work, setting up our house properly helps our mind to shift into work focus. A dedicated space makes all the difference. You can find an interesting mental model about this here.

The most important thing you need to do is to create a specific workspace in your home. Some people really hate the idea of mixing work and home spaces, for others it might not seem a big deal, especially if remote working is going to be just for a few days or weeks. Regardless, it’s still advisable to create a suitable work area as it’s one of the key factors to preserve good mental health when at home.

In order of preference, these are the approaches you can have to setup such a work area:

  1. Have a room dedicated to it. When you’re in there, you’re working, when not, you’re not. Having an entirely separate space helps our mind to connect and disconnect easily, and thus creating a healthy separation.
  2. Have a corner with a table dedicated to it. While not a separate space, dedicating a corner is similarly effective to achieve separation.
  3. Have a room configuration dedicated to work. If you don’t have a room or a dedicated corner and table, the next best thing is to make sure your space looks different when you’re working. A simple way to do it is to have a different light configuration: you can buy a good light, maybe even colored, and you turn on that light (and off everything else) only when you’re working. Your brain will associate that light configuration to “work”, thus helping again to create a distinction.

Try also to have some kind of clear background for calls, and ideally not have the area behind you a passage area of the home, especially if there are other people in the house with you, so you don’t disturb them and they don’t disturb you.

Make sure your space is as well lit and as ergonomic as possible. As much as it might feel appealing to work from the sofa or from the bed, it might create strain even just after a few days.

Start and End Rituals

How can I set the pace for my day?

While distractions can be something to deal with at home, usually people that work remotely don’t have them at the top of the list if they set up a good workplace. What’s there instead is not knowing where the day starts and ends: as there are no other people around you to make you feel the rhythm of the day, it’s very easy to lose cognition of time, and go on working beyond healthy work hours.

It’s thus advisable to create a daily ritual that works for you. For example you could get out every day to get a coffee in the morning, and have a shower once you finish working. Or maybe have a walk. Or brew some tea. Experiment with a few different ideas and see what clicks.

Another technique we personally used when the days were particularly flexible is to set a timer for 8 hours of work. When it rings, we know we should be closing, regardless of when our day started in the morning.

Have breaks: not just for your mind, but also to move the body a little bit. Short of a gym, do some exercise, stretching and movement. Your body will thank you.

Setup your Camera

How to make your video calls more effective?

Even if you work with the most text-based company in the world, it’s likely you’re going to have at least one or two calls during the week — if that doesn’t happen, we’d still advise you to do at least one for socialization purposes!

Setup your camera and room lights so you are well lit, and if possible get a led light that you can use specifically for this purpose. 

It’s also important to try to look at the camera, not at the screen. This makes you feel more connected and present during the call. To help this, you can just resize and move the window with the others’ video to the top, so it’s as close as possible to the camera and even if you look at them it still seems you’re looking at the camera.

If other apps distract you, try to run the video full screen or in a separate virtual desktop. Some people even use a separate device only for the calls: if you happen to have a tablet or a phone on a stand, you can make all the calls via that.

Some apps, like Zoom and Microsoft Teams allow to set an image as a background or blur it, which can work great and make you less self-conscious about the room you’re in.

Distractions, and ADHD

How can I limit distractions and interruptions?

Distractions can be challenging when working from home, especially if you have attention deficit hyperactivity disorder. The space around you can create many distractions, so it’s important to try to be prepared on how to deal with them:

  1. The workspace is very important. Try to have it as separate as possible, especially if there’s someone else in the house (maybe they are working from home too…).
  2. If other people are at home at the same time, talk to them and discuss how they can disturb you if needed. A good strategy for this is to act “as if” the person is at an office: just send a message instead of going to them and tapping on their shoulder.
  3. Clear the desk, and what you see right around your screen. This might seem small, but reduces the chances of the mind wandering.
  4. Take breaks, take a shower, have a walk, take a 10 minutes nap. While it might seem counterintuitive to stop working if one is too distracted, it’s a viable technique as it helps to recharge and refresh. 
  5. Have meals ready in advance, or just the ingredients, so you don’t have to decide and it’s easy to do.
  6. Dress comfortably, but still make sure you take care of yourself.
  7. Have separate “personal” and “work” profiles on your computer. 
  8. Chores might also attract your attention. A way to avoid this is to remind yourself that you managed to do this working in an office before, and maybe make a list of the chores so you can plan them over the week. This might seem a lot, but just offloading the chores to a note for “later” might free up your mind.

It’s not all bad however. At work there are many other kinds of distractions that we can’t avoid: colleagues walking by, talking nearby, coming to our desk, general office noise, and so on. At home some of these issues disappear, and even more we have a larger degree of control on the environment around us.

For more details you might want to check this Twitter thread.

Decisions, Decisions

How can we make sure decisions are taken and are properly surfaced?

Make sure every decision that happens in a voice call is written down somewhere. This should already be how your company works regarding meetings, but we noticed that working in an office often assumes that information discussed in meetings is “known and shared”. 

Remote working and calls make this harder, as calls make meetings become invisible: you won’t even know that a colleague had a meeting, so there’s no chance to ask them, or to see that something happened.

Making sure that decisions are tracked in written form is good practice, and once you do it even if you go back to working in an office you’ll want  to keep doing this because it’s so much better. 

Kill Meetings, You’ll See Why

How can we avoid falling in a tunnel of endless calls?

We’ve never found any organization that didn’t do useless meetings, and if yours is like the most, you’re likely doing meetings for things that can be done in text. Text is your friend, it allows more reflection time, and more people to engage. You might have to find ways to figure out on how to do something in text instead of in a meeting, but it’s totally worth it — the benefit is that you’ll gain even more flexibility as you can review the decisions and discussions when you are ready, not when the meeting is scheduled.

Watercooler Spaces and Socialization

How can we preserve the social interactions that make work more human and meaningful?

An office provides plenty of occasions for people to socialize, know each other, and see the other people as more of their role in the company. When working remotely, these random moments disappear entirely, as such, they need to be explicitly created.

This means it’s important to allow for the human side to surface. A lot of people fear that too much chatter makes people unproductive, but that’s a fear we rarely witnessed first hand. Usually people don’t socialize in chats because “chat is for work”, and the fear that chatting makes people less productive never materializes. 

Main advices for this:

  1. Allow socialization to happen in chat channels. Chats are the best for it because messages get old quickly, and if a work discussion starts it’s easy enough to interrupt the social side.
  2. Create special channels for purely socialization. Maybe you have existing socialization channels, like a team whatsapp group or telegram, maybe not. Anyhow, when work becomes remote, trying to recreate a “socializing virtual room” is very important, as much as it’s crucial to make sure it remains a place “for fun”. Having a #watercooler channel for example is a good one, but also having themed ones, like #cats (memes of cats), #emojis (where people can only talk via emojis), or #photography (let’s talk about our shared passions). 
  3. Bring some fun in calls. When you have a video call, consider also that it’s one of the few situations where you interact live with someone, thus try to consider also the social aspect of them. While there’s no need to do ice-breakers and explicit social activities every time, five minutes of light chat might work. Experiment and see what’s effective for your team.

We can also suggest installing Snap Camera, and use it when you want to add some element of fun in the call. If not overused, this can help make calls a bit more fun. 

Making Our Presence Felt

How can we recreate the sense of presence and availability within the team?

Working remotely might make people feel less together, so it’s important to make sure your presence is felt by the people you work with. For some people that usually relied in the office environment this might be a challenge.

One good technique is to have an asynchronous text standup at the beginning of your day: when you start working, you type in your team chat (or equivalent) what you did yesterday and what you plan to do today. And on top of that, you can also add maybe something personal, non-work related. 

Another thing that works for some people is to just type in the team chat when they switch work, saying things like: “Switching to work on X…” and nothing else. This creates context, awareness, and socialization moments.

And again, this doesn’t have to be strictly work related. Even mentioning something as mundane as a home delivery or mentioning the lunch you just had can be effective.

For more insight on presence, check this other article.

Feeling Alone

How can we avoid feeling disconnected from everyone?

A lot of introverts that never worked remotely might underestimate this, but ultimately regardless of being introverted or extroverted feeling alone is something that everyone might feel at some point. While the practical solution for this can vary from person to person, try to identify when the feeling arises, and ways to balance it.

Sometimes just a walk to grab a coffee can help. Or having a moment in the day to call a friend. Or might even be a coffee break shared with the rest of the team. If the circumstances allow, even working from a cafe or a coworking space for an hour or two might help.

In short, if you feel you’re not having enough people time, try to find it explicitly. Often, your team will benefit from it as well.


Do you have any other tip you would give to people starting to work remotely? Reach out!

More Resources

This article was co-authored with Meg Pagani. Thanks to Riccardo Cambiassi for integrations to the original post.