How and Why Remote Work Works

*This is about a 16 minute read and may be used as a reference tool. It does necessarily need to be read from start to finish. Some points are repeated throughout different sections intentionally.

Given the current situation around the globe, you may be reading many articles about remote working. Many of them have great insights. In this article, I will share my own personal experiences and attempt to share some very practical advice, which you may not see in those articles.

In 2015, I began a new job with a new employer. Along with the usual challenges of starting a new job, I had to learn to work remotely, something I’d only done during snowstorms or other extreme circumstances before. The company had recently moved toward a remote way of working and the team that I came in to lead was spread around the United States.

Around the same time, during nights and weekends, I began teaching User Experience Design courses at a school called General Assembly. I taught both in person and remote courses, which gave me plenty of chances to experiment with the differences.

Meanwhile, in my day job, on top of the regular weekly team meetings, project kickoffs, check-ins and 1:1’s with each other (all remote), my team and I design and facilitate workshops and design sprints for other teams and clients. About a third of those workshops and design sprints are remote for one reason or another, which I reference in this interview. We’ve run numerous 5 day Remote Design Sprints, the first of which I wrote about here.

Over the last 5.5 years, remote work has become a regular and comfortable way of working. But it didn’t start that way. It has required countless experiments. Now that so many have been thrust into remote work by coronavirus, I am sharing this list of tips, tricks, pitfalls and surprises about remote work. Thank you to my amazing colleagues Greg Smith, Nicole Norton, Corinna Snyder and Jacqueline Hwang, who contributed to this article and with whom I get to experiment every day.

Embrace the differences between in person and remote working

It’s common to assume that there is a major drop off in effectiveness, engagement and productivity if a team works remotely. In my experience, it’s just different. Some things are easier in person, but not all things.

I recently went through a major renovation on my home. We changed a lot. One of the biggest challenges was trying not to adhere to the constraints of the house as it was. It was hard to imagine a wall being relocated, a door shifted over, or the kitchen being in a different place. We had to work hard to drop the existing constraints to reimagine what it could be.

In person teams may struggle similarly if they choose to (or are forced to) rethink meetings, workshops or other activities to be remote. It’s tempting to simply try to recreate what you’ve done in person and it can be difficult to forget the constraints of the past.

A few years ago, my team and I were working on the design for one of our first fully remote workshops. (Note that we all work remotely with each other normally and tend to be together only when we do an in person workshop, something we also do quite often.) As we were designing this remote workshop, we reached one part around collaborative prototyping. We were really struggling with how to recreate the great, in person collaboration that we’d seen with so many prototyping sessions in past workshops. We kept running into reasons we couldn’t recreate it. Then we agreed to take a break (and a walk). During our respective walks (we were all in different locations), we each had a moment to rethink our dilemma.

When we returned, someone suggested we flip our thinking. Instead of attempting to recreate a great in person activity, we asked the question “How might we take advantage of being remote for this activity?” That question and mental reframe changed everything for us and the ideas began to flow. We saw advantages we hadn’t before. We saw that there was an opportunity for generating ideas separately and individually — something difficult to do sitting around a table. We saw that it would be easy enough for each person to take photos of their own prototypes and post in our shared virtual collaboration space. We saw that capturing notes and feedback on each person’s ideas could be far faster since we can pretty much all type faster than we can write… and we wouldn’t be constrained by a physical wall space that a finite number of team members can reach and write on (how we’d done it in person).

The point here is that in person or remote isn’t a better/worse comparison. It’s just different. Embrace the differences and play to the strengths of each setting.

Don’t assume you can’t accomplish work in a remote setting

People often make the assumption that to achieve good outcomes in a meeting or workshop, you have to be in person. In my experience, proximity is just another factor to consider, not all that different from any other. There are times when being in person is very beneficial. For example, in some of our workshops we have helped teams prototype and test physical spaces like offices or trade show booths. Those are very tactile, in person experiences. Therefore, during the prototyping and testing portions, it’s usually important to be in the same physical location. In cases where that isn’t an option, consider creating storyboards in place of prototypes and gathering reactions from virtual testers to those. It’s not as good as allowing a user to truly feel the experience of something, but it’s still pretty good. In the end, proximity matters much less than one would think.

The super power of anonymity that is unlocked by remote working

Being remote provides something that can be invaluable — anonymity. No matter how hard we try, it’s hard to shake the feeling that the second you share an idea in a room full of people, it’s being judged by everyone. Even the best leaders who create an environment of openness and a culture of experimentation may not be able to tamp down the social anxiety of sharing ideas. Remote work changes this dynamic. It’s like the feeling of wearing a mask on halloween. All of a sudden, people don’t know who you are. There is some freedom in that. In a remote setting, it can unlock previously untapped creativity.

My team and I often refer to this phenomenon as “working together, alone”. We are very intentional about when it’s time to work individually, anonymously and silently. And we are just as intentional about when and how we lift those constraints.

When no one will know who’s idea is whose, the creative floodgates tend to open. People share things they wouldn’t have because the personal judgements go away. If you can keep that anonymity in place for decisions, then you truly have a team effort. You can achieve shared ownership of an idea, goals and outcomes. Wherever possible, we make sure that no one ever knows who came up with the ideas. It allows team members to individually own their tasks towards a collectively owned outcome.

The tools do matter, but don’t start there

Many people ask me what tools we use for remote working and collaboration. The answer I give usually frustrates people. It depends. Yes, some tools are better than others, but avoid the trap of focusing on the tools first. Before you do that, think about what kind of experience you want for your meeting or workshop. Is your meeting about coming up with ideas? Making decisions? Sharing decisions? These are all very different types of meetings and shouldn’t be handled the same way. See more on meeting types here. Once you have decided what kind of remote meeting this will be, then you probably need some of the following tools. I won’t call out specific ones since every organization has their own rules and restrictions about what tools can be used, but if you’d like to hear my personal opinions, message me directly.

You will need tools that allow for:

Communicating

• Video conferencing
• A chat tool for quickly sharing links, images, gifs, memes, etc (don’t underestimate the fun factor — memes build personal connections!)

Collaborating

• Screen sharing
• Virtual breakout room capabilities (not a must have, but needed for some types of meetings or workshops where group work may be needed)
• A cloud based file sharing tool so everyone has easy access to the same version of the same things
• A virtual collaboration tool, ideally one that allows participants to remain anonymous, which can be a huge benefit

Creating

• A digital prototyping tool (not a must have unless part of your meeting will involve creating early versions of ideas to be tested)

Energizing

• Music! This ties back to energy levels and can make all the difference. We have a couple of playlists we use and sometimes we just spin the wheel of music (yes, we have a wheel). Also, if you can, use a screen sharing tool that also allows you to share audio into the video conference so the sound quality is better.

Don’t collocate clusters of people just because you can

Oftentimes, teams have clusters of people in one office and individuals who may work from home or be the only one in another office. When it’s time to have a meeting or working session, it seems like a no-brainer to have the colocated people get together in a conference room while the individuals join individually. It feels like the right thing to do. But if your meeting needs any amount of collaboration, don’t do it! This dynamic almost never helps. It leads to side conversations and disproportionate opportunities for everyone to contribute. The message gets lost, the contribution is uneven and participants leave feeling frustrated and distrustful.

There are two scenarios where collocating may work, but approach these with caution.

• When delivering a one to many message — Think of a town hall meeting where someone may be on camera speaking to a large group, sharing information relevant to all. This can work as long as you are intentional about how questions can be asked and answered. Call outs on a conference bridge will lead to pure hell unless the group is very small. Instead, set up a form or chat window where questions can be submitted. Then have people managing those and funneling them to the speaker, who should read aloud and respond to the question.
• When breakout teams can be the same as collocated groups — My team and I have done this. In one 2 day workshop, we had teams collocated in 4 cities (Atlanta, New York, Tampa and Chicago). In order for this model to work, we had 1 lead facilitator fly to each location to sit physically with that team, while one of those leads, who happened to be me, also played the role of overall lead facilitator. We designed the workshop to have portions where all 4 teams connected over video conference, then would break out with their teams to work on something, then come back together again. It worked well, but I warn you it can be a logistical nightmare. Take whatever preparation time you think you need and double it, because you will have 4 rooms to set up, 4 sets of A/V equipment to work with, 4 sets of localized distractions (a fire alarm went off in one location) all to contend with. It is not for the faint of heart.

Make sure everyone is able to join in a way that allows them to participate fully

Related to the points above, it’s important to set expectations in advance for all participants. If you need to verbally share a message one way, a telephone conference bridge might do the trick. If you need to view something over a screen share, make sure everyone knows that and is able to join in a way that allows for that. If everyone will need to collaborate through a virtual collaboration tool, make sure everyone can be on a device that allows for input. If people don’t know these things in advance, someone may think they can join while driving from one place to another, only to learn that they can’t contribute because they can’t be on their laptop.

Assign roles intentionally

It’s important to assign and define roles in all types of settings. In a remote setting, you will need a few roles that don’t tend to exist in person. Here are ones we often use:

• Lead facilitator — This often exists in person as well. In a remote setting, assigning this role is critical. This person will manage all aspects of the session. They own the agenda. They own the decision to veer off the agenda if needed. They are the CEO of the meeting.
• Titan of tools — You will likely have video conferencing, collaboration or creation tools in use to support the session. The lead facilitator should not play this role. It’s too much of a focus taker. This should be a separate person who is there to make sure everything runs smoothly allowing the lead to focus on making the session as effective as possible.
• DJ — I’ve mentioned music in other sections and will again. I can’t stress enough how important music can be to energy levels. The Titan of Tools might be able to handle this, but they might have their hands full. Music is important enough to ensure it doesn’t get lost in the shuffle, so dedicate someone to this. They will love it!

How to stop everyone from talking over each other in a remote setting

Much like monitoring energy and interest levels, we humans rely heavily on physical cues from each other to manage conversation. When everyone is in the same room you can see body language that may indicate someone has something to say. It might be a subtle lean, a clearing of the throat. People may even raise their hands. In a remote setting, at best you probably see people from the neck up, amidst a grid of faces. But people don’t always turn their cameras on and even if they do, it’s difficult to pay attention to all of them, depending on how large your meeting is.

So what can you do? Here’s what I recommend.

• Don’t try to recreate the in person experience. It’s a different setting. See this section on embracing the differences.
• Avoid open ended, untargeted prompts like “does anyone have any thoughts?” Remote or in person, I generally feel these prompts are a bad idea and lead to unproductive discussions, worsened by being remote where social cues are mostly lost.
• Instead, set up ways for people to contribute without talking. Collaboration doesn’t always need discussion and it often suffers because of it. Use a shared doc or collaboration tool and allow people to contribute there. Make it clear they should only contribute if they have something to contribute. Much like asking “does anyone have any thoughts?” people may feel like they have to come up with thoughts just because it was asked. Also, if people have contributed silently to your shared collaboration space, don’t feel the need to verbally respond to any of it. Move on.
• If you are making a decision, use a virtual voting tool instead of discussion.

How to build trust and camaraderie in a remote setting

Like many other things on this list, it’s helpful to embrace the differences. It’s also important to acknowledge that much like being in person, there isn’t one single trust building moment. It’s a combination of moments, many of which are mentioned in this article. For some quick tips, go heavier on the warm ups using a virtual collaboration tool. Play games like “one word story” where each person types in a word to add to the story, one at a time, silently. Play a game like 2 truths and a lie, or 1,000 uses, one of my personal favorites. There are plenty of ways to build rapport with each other that don’t require you to be in the same room. My team and I even held a virtual holiday party this past year, complete with an ugly sweater competition.

What about the loneliness?

Yes, it can feel lonely and isolating to work remotely. I can’t point to one set of strategies to combat this. My best advice is to follow all of the other advice in this article. For me, all of these combined have helped me feel connected to those I work with. My one personal hack is to work from a couple local coffee shops for parts of a day. That only works when I have a good chunk of heads down, earphones-on work to do, since most places are too loud to comfortably contribute over video or phone. But the temporary change in setting always helps. I’ve experimented over the years with different personal strategies and I recommend you do the same.

Managing Energy levels

I get asked a lot about managing energy levels. It’s challenge because the lead facilitator has different data to work from in a remote setting. Slumped shoulders, subtle yawns or big smiles may be more difficult or impossible to detect. Video conferencing helps, but you just don’t know. Someone could be binge watching The Office. Here’s what I recommend in no particular order.

• Pay attention to your own energy. If you are the lead facilitator, this always matters, but I’d say it matters much more in a virtual setting.
• Skip the round robin intros. In general, I think intros at the beginning of a meeting are a waste of time. Unless you are meeting before robbing a bank and absolutely need to know each person’s role and how their skillset will be used in the heist, skip this step. Just get to work. This is even more true in a remote setting where people can more easily tune out.
• Encourage people to be on camera but make it totally optional. If the medium is a video conferencing tool and you are the lead facilitator, you should probably turn your camera on. That might make others feel more comfortable turning on their cameras. Either way, be respectful towards those who aren’t. Don’t make people feel bad if they don’t. You never know what others may be dealing with on their end.
• Do a warmup that everyone can easily participate in. Intros are not a warmup and you already know how I feel about those. Do something simple. Use a remote collaboration tool and play a quick game like “1 word story” or “1,000 uses” or “collaborative sketching”. Cap this activity at no more than 5–7 minutes.
• Give people a chance to get focused. In those first few minutes when you might be waiting to get started, ask everyone to write down, on their own, one thing that is on their mind that may prevent them from being fully engaged in the session. Then give them 2 minutes to do one small thing about it. That might be as simple as turning on your out of office, sending one quick email, or just getting something to drink.
• Play some music at the start. This is simple to do. Pick something up beat and energizing. And if you happen to be using a video conferencing tool that allows you to share audio (some do), play it that way. The sound quality will be much better.
• Check in along the way. At the beginning, we tell people that we will be checking on energy levels along the way and that it’s 100% encouraged to call out if theirs is low and they need a break. Chances are they aren’t alone. Even a 5 minute break can help people reset. It’s worth the investment.

Keeping people engaged

There is no silver bullet here. All the tactics above and throughout this article will help. I will say that the best way to ensure engagement is to include people who want to be there. This may seem obvious, but people often invite others to a workshop or meeting for the wrong reasons. I’ve heard comments like. “This person should be there.” or “If that person isn’t included they will be offended.” or “This person is the expert.” Beware of all of these, especially inviting the experts.They can be helpful or they can cause others to shut down and defer. Get to know the expert first and be sure they want to be there.

Managing distractions

People always ask about how to manage distractions. It’s a great question. One major downside of remote work is that in order to do it, you need to be sitting right in front of the distraction machine. Technology like chat, email, video and tons of collaboration tools has removed much of the communication friction that once existed. Unfortunately all that friction removal has created a whole new kind of friction, created by all the distractions.

So what can you do? First, accept that you will lose a few. Smart people have spent years designing products that will grab and hold your attention, no matter what context you are in. Push notifications on a phone are designed to do exactly this. You can’t stop that train. What you can do is make some recommendations to people who attend. Here’s what I recommend.

• In advance, make sure people know how they should connect to the meeting. Let them know if they need to be able to see a screen, share a screen and if they need to be able to speak or just listen. Set expectations.
• If it’s a workshop or large working session, ask people to only join if their schedules are clear. I’ve had many people contact me before a workshop to let me know they will have to miss a block of time. I tell them they should probably just skip it altogether. It’s usually not worth it to get those people back up to speed. Also, their lack of context hinders the group’s ability to move forward.
• Ask them to close email and shut off notifications.
• Set the expectation that this may require extra focus and discipline, but that it will be well worth it and the outcome for the commited is usually a feeling of trust, camaraderie, accomplishment and exhaustion.

Dealing with time zones

Last but not least, one advantage to being in the same physical location is time. If you are in the same place, you are in the same time zone. This makes decisions like when to start and end easy. In a remote setting, this is more difficult. Recently I led a remote workshop that had participants from California to Malaysia and many places in between. We started at 8am ET, which meant a very early start for some and a late night for others. If you find yourself in this situation, be sure to set expectations with the participants about how they will need to be engaged. Our workshops are highly interactive so being in front of your computer, with the camera and mic on and a quiet setting are important. Dialing in while dropping the kids off at school won’t allow that person to participate effectively, so we make sure that whatever time we pick is one that allows each person to fully participate.

Those are the main ones from my experience, but I am learning every day and will continue to add to this as I do. I hope you all find this helpful and I welcome other comments, tips and tricks!