How To Transition to Remote Work

Companies transitioning to the work-from-home model became the recurring theme of the last month. I've spent more than half of the previous decade working in remote teams and have seen quite a few transitioning from the office to full-remote processes. Actively advocating remote work to everyone I know, I feel having to put a few cents into the tip jar.

To get an idea of what the current remote working plane looks like, I recommend digging through some data. Buffer and AngelList had created an excellent study, "State of remote work 2020". I've found most of the things presented there highly correlating with my observations across the field. Also, there is another study that is released by OwlLabs, representing some other useful points to keep in mind. I recommend reading them to get some valuable insights into the struggles and benefits modern remote workers are having in their companies.

Disclosure: I don't work for any of the companies mentioned in this post. All the apps listed here are just the examples I have seen in the wild. The tricks described here had worked out great for me in the past not only for building the remote teams, but also to heal the problems and increase the performance of the office-based companies. 

0. Don't be afraid of changes

The modern world is moving fast, and we should be able to keep up with the changes. Do not marry your tools or processes. If something is not working out, sometimes it is better to replace the app or rebuild the process instead of trying to fix something that does not quite fit. Embrace the changes instead of fighting them and see the outcomes this attitude leads to.

1. Build and gradually refine your framework

With the right approach and motivation, building the remote team becomes a fun and exciting experience. Some of the issues in the current processes are often visible, and the team can tackle them early in the process. What worked out great is keeping the list of the problems the team encounters in the new environment and working through it to find better methods and tools that help to deal with the nastiest ones.

Building the best framework for the team should be the iterative process with everyone involved. Working from home or other remote locations introduces team members to the new not-so-obvious problems, and fixing them together usually leads to the motivation and performance boost.

There are lots of examples out there, from increased length of daily standups caused by connection or audio issues to team members struggling with the working schedule due to distractions. The first one is usually straightforward, and the team can fix it by using other communication software.

I've seen people hopping from hangouts to zoom, skype, and even FaceTime to find the right tool, but once it clicks, everyone becomes happier and more productive. The second one has a few different options, such as renting the co-working space for the struggling team members or paying for members' coffee in their local coffee houses, but it looks like these are not very relevant at the time. Instead, the team could transition from synchronous to async collaboration model and allow flexible working hours for the members.

Start building your list with the existing collaboration processes in your team. Then try to transform that list into the remote model, if something is not mapping right, think about changes in the process and tools that can help with that problem.

For example, showing something on your screen to your teammates is something trivial and can be easily encountered in most office environments I was working in. Still, collaborative coding via skype or zoom feels clumsy. There are plenty of tools like teletype or floobits out there to scratch remote pair programming itch. Another creative solution I've seen was using the miro board for system design discussion instead of whiteboard.

But don't get carried away by finding the tool for every problem you are trying to oversee early. Overwhelming people with new applications and processes could be daunting, and their performance will decrease. Instead, keep your remote framework lean and introduce new tools gradually as you encounter the flaws in the existing processes.

2. Tighten your feedback loop

Remote working can be challenging for some team members. While some people are thriving in such an environment, others don't. It is much better to detect the problems earlier than fight with the consequences afterward. Consider increasing the frequency of 1-1 meetings at least for some time to be aware of the current situation.

In addition to regular 1-1s, try to come up with alternative sources of the healthchecks for your team. Setting up the small daily check-ups had led to insights hard to be overvalued. If you want to implement something like that, there are few things to keep in mind. First, they should not be huge, sometimes less means more, you don't want to have your team crunching through the list of 45 questions daily.

Second, they should not be disruptive. If you're going to do those check-ups in the form of a few questions during the working hours, it is not a very bright idea to pull the team members out of the "flow state". Third, consider making this anonymous. Some people feel much more comfortable talking about their problems anonymously. Make it clear that this addition is to help them with complications, not to spy on their working day.

There are plenty of tools to build something like that from strawpoll to abot and facebook workplace polls. Make it fun, and people will like to share their issues and concerns with you.

3. Make sure everyone has access to the required equipment

This one is obvious but often overlooked. Even with the most excellent remote framework, people without stable internet and working laptops won't be able to do their work. An office environment exists to provide essential tools for team members to do their job, but home is a different thing. Consider covering some costs for your team members such as the internet or food expenses (if you were offering some type of free food at the workplace).

Supply people the necessary equipment for their home offices such as laptops, headphones, mic, and even a table with a comfortable chair. People working from home have the same needs as people working from the office, just pay attention to their needs, and you will be surprised by the results.

Also, I want to emphasize covering some food costs. Sometimes companies fail to realize how much of their employees' income distribution planning is influenced by the free perks offices are providing. Please, discuss this with your team, don't let people starve.

4. (Async) Communication is the key

The biggest mistake I've seen is leaving the communication model untouched while transitioning to the remote model. The office offers the luxury of synchronous communication and collaboration. Micro-chats are happening in the office environment all the time, leading to better knowledge retention, synchronization, and prioritization.

The most successful transfer I've seen was with the team that already had adopted the asynchronous communication and collaboration model. After their daily standups, they would send out recap emails to all team members, and most of the discussions were text-based instead of meetings. This method alone led to a significant increase in the team's performance and quality of their conversations.

Asynchronous communication basically means the sender does not expect the immediate response after sending his message. I'm a fan of this model; it allows parties of the process to stay in "flow state" for as long as they need. The other part is that it leads to more meaningful and thoughtful responses increasing the value of the process itself.

Not every conversation should be handled asynchronously though, for example, brainstorming some ideas this way could lead to missing valuable insights due to some self-censoring happening in text-based communication. (Is this too stupid? Yeah, it's dumb, won't send. — The idea that led to another idea which led to a $1M profit increase had just gone). But in general, try to move away from the synchronous model as much as possible.

Another trick is to keep these discussions closer to their subject, reducing the issues with the missing context. Move PR/code review/design decisions to VCS UI, task discussions to the task management system, UI/UX discussions to respective collaboration tools you've chosen, etc. This change helps with knowledge retention and distribution and allows parties involved to handle multiple conversations asynchronously. Recalling the context is another underrated feature of asynchronous communication, which becomes handy in the remote environment.

But what if the receiver ignores messages? A few possible problems are leading to this situation, but two simple tricks could resolve most of them:

1. Gather all the sources of the discussion in one notification feed for each person. For example, it could be email or slack/other messaging platform bots. Make sure everyone involved in the conversation is receiving all the information they need.
2. Set up some "Inbox Zero"-like policy for that notification feed.

5. Syncing up

Asynchronous communication and collaboration models are introducing the new challenge: How to keep everyone in sync? Unfortunately, you can't throw a bunch of mutexes into people and fix that problem. You have to establish the cultural behavior of keeping everyone in the loop by reiterating tasks on dailies, maintaining logs of critical discussions and decisions, making sure the tasks are visible to everyone, introducing meaningful statuses, etc.

As an example, I've seen the team building their slack bot to send smart notifications to responsible people if other tasks on Github blocked theirs.

A few tools are helping asynchronous teams to sync up, such as idonethis and Status Hero. They can be used to track everything your team is working on, the team's goals, current blockers, and other useful stuff.

6. Flexible working hours

As mentioned above, allowing remote workers to have a flexible schedule could be used to solve some common problems. Besides, building the team's remote culture with flexible or floating working hours will be very helpful once the team grows global. Remote working model opens up the gigantic pool of talents across the planet, so why hesitate and try to squeeze everyone into one timezone?

But having the team distributed across the different time zones is one of the issues remote employees are struggling with. Essentially this boils down to lack of asynchronous communication and lousy synchronization. Hence, the general advice is to try to build those processes with the possibility of having members working at a different schedule. It would be great if everyone in the team would have some overlapping working hours to hold dailies or other syncing up meetings.

To keep everyone synchronized on timezones, it is a good idea to create the team availability calendar. Some tools already have that feature, but there are products built precisely for that like Spacetime or Timezone.io.

7. Fighting the loneliness

As stated in Buffer's research, one of the biggest struggles remote workers are facing is loneliness. The office environment is full of human interactions, and the home office is usually the opposite. Loneliness is a complex issue, but few tricks could help prevent it from happening to your team members.

The first one is to set up the video/audio conference room where everyone signs in when they start their working hours and signs off once the working day has come to its end. This technique helps people feel engaged in teamwork even if everyone is on mute for the whole day there. Another great option is to pair the team members randomly with each other for the working day. This method not only leads to better relationships between your teammates but also helps them to feel less lonely.

In addition to that, you can set up the social channel/room where people could casually chat about the things they want. It helps to keep the team social interaction healthy and to fulfill the human desire to be part of the social structure. For most people, it could be weird at first, but when they get used to it, it feels more natural than water-cooler chatting.

Also, come up with fun, remote non-work activities for your team. Such as online game tournaments, watching movies or conference talks together, or just skype pizza parties. Remote workers are the same kind, and they like to hang out too.

You can reuse the same tool team is using for meetings to make this happen. Zoom rooms or hangout groups are working great; also, I've seen people using discord and loving it.

8. Motivation and distractions

One of the common fears I've faced is that people won't be able to keep their performance while working remotely due to the number of distractions they are facing in a remote environment. The possible solution for this is to expand mentorship and coaching beyond the professional field and teach team members some time management techniques.

Pomodoro, GTD, and others can help you and your teammates to stay focused on the work in the working hours and sign off more smoothly at the end of the day.

The other struggle mentioned in the Buffer's research is the team's motivation. Keeping everyone motivated is a big topic for covering here, but the one thing I've seen useful is to be as transparent with the team as possible. Precise definitions of the goals and visible progress can play a crucial role in keeping people motivated. You can build dashboards for your team to track and visualize critical indicators of your goals with the value each of your team members brings in.

9. Helping people to sign off

I've witnessed people missing this one too many times. Buffer's study confirms my observations that people tend to overwork or significantly hurt their work-life balance while working from home. Stress, anxiety, burnouts, lost focus, and motivation, I've seen it all. It is hard to relax when your working place is right next to your sofa.

I've found building the sign off routine for your team members early vital. It could be anything helping them to divide their day into "work" and "life". Asynchronous teams could use separate channels for checking in once they start working and sending goodbye messages once they are heading off. Make it fun, let's say it could be a channel where everyone can post only gifs or memes, songs are working out great too. The idea is to distract people with non-work activity before they are signing off to put their minds into a relaxed state.

For people working in the same hours, it could be the "sign off call" with a ban on work-related stuff, where everyone is saying goodbye and chatting about their hobbies, new music albums, or youtube videos.

Recap

Transitioning from the office environment to full remote is a complex task, but if done the right way, it could be an exciting opportunity for your team and company. Working from home is very different from working at the office; there are quite a few challenges for the teams to overcome to become successful in the remote environment. Some simple steps help to make the transitioning process less painful and more fun. The general bits of advice are:

1. Build an initial remote framework using the tools team is already familiar with
2. Teach the team remote culture
3. Keep track of the issues the team members are facing
4. Find the right process or tool for each issue
5. Iterate

Further reading

If you haven't read the two studies I've mentioned in the beginning, give them some love, they show some insights from the remote work environment:

• Buffer & AngelList
• OwlLabs

Heroku is well-known for having remote teams; there are a few blog posts and podcasts about their remote-first journey:

• On Making Work Less Remote: How the Heroku Team Works Together
• Making remote work
• Making Remote Work Work

Nick Francis has a great blog post in Help Scout blog — What We've Learned Building a Remote Culture

And of course, the great book by Jason Fried and David Heinemeier Hansson — REMOTE: Office Not Required.

Tools

There are plenty of tools that a remote team can use for daily collaboration tasks. Still, I encourage everyone to think about existing processes, analyze and refine them first, don't pick the tool if you are 100% sure your team needs another one. If you are confident you need one, you can find the vast list of applications at remote.tools.