Rules for remote work

I’ve worked remotely since 2017, both as an employee and as a founder. When we all locked down in 2020, I saw everyone thrown into chaotic remote working situations they had no time to prepare for. At that time, nearly two-thirds of employees polled “felt like the cons outweigh the pros” and a third considered quitting altogether. Four years later, remote work is now an intentional choice made by many organizations—but I still hear my friends complain about their continually dysfunctional remote cultures.

I think that’s a shame, since I’ve come to love the benefits of being remote: working wherever and whenever I’m at my most productive and creative. I’m able to collaborate with teams spread across the country, with people living fascinating lives on their own terms, and maintain a healthy balance between my work and my life. The benefits of eliminating a daily commute cannot be understated, either.

When a company doesn’t have a strong remote culture, avoidable stresses and conflicts become inevitable. There’s no training for an office that suddenly shifts from in-person to on-line when managers are learning in realtime along with their employees. The work never stops, either. There’s no chance to regroup and rebuild a remote culture from the ground up. Changing a company’s culture from the grassroots is difficult when you not only need buy-in from managers, but need them to be the ones leading by example.

Here’s what I’ve learned about how to build a positive, functional remote work culture. These lessons cobbled together from personal experience building remote workplaces, informed other remote-first companies like Automattic and 37signals (a note to remote managers: there are books written about this and you should be reading them!). In retrospect, the best time to have have written these down would have been April 2020. But, as the old saying goes, the next best time to have written them down is now.

1. Escalate mode, not tone.

If there’s a golden rule for remote working, it’s this one. There’s a nasty cognitive bias where we read negative emotion into innocuous messages. Like a ship’s crew maintaining their boat against salty seas, workplaces need to be constantly counteracting the corrosive effects of negative intensification bias.

Fortunately, we have the tools to avoid this. As soon as you start to read negative emotion into a text conversation, switch to an audio call. When you switch into a higher-resolution medium, you can hear someone else’s tone, instead of trying to infer it. If a phone call becomes testy, escalate it into video. The more you can see and hear somebody, from audio to video to an in-person meeting, the easier it is to build empathy, resolve problems, and keep your relationship constructive.

This isn’t to say that tension and negativity may be avoided altogether. But if a discussion is on a sour subject, or has the potential to curdle, start it from the highest-resolution medium available and deescalate down from there.

2. Limit communication to specific, enforced hours.

One of the huge upsides of remote work is the flexibility to work when you’re at your most productive. One of the huge downsides is feeling like you’re on-call at all hours of the day. In the US we paradoxically view overwork as an elite signifier; in reality, the overworked are “less efficient and less effective,” more likely to feel depressed and anxious, and experience declines in creativity and judgement. It’s a fallacy to think that working at all hours demonstrates a commitment to success; it only leads to burnout.

Let work happen at any time, but try to limit communication to an agreed-upon window of time. Try to avoid sending emails or messages during this time, and don’t expect any responses if you’re communicating outside that window. Unless one of your specific responsibilities is monitoring resources that need to always be available, the business won’t fail because you waited until tomorrow morning to reply to an email. This is critically true during vacations or holidays when an office is meant to be closed.

A friend of mine here in Indianapolis (Eastern time zone) was just telling me how she works remotely for a company in Portland, Oregon. Her office’s hours are 9am Pacific to 5pm Eastern, which sounds amazing. This policy respects everyone’s schedule while expecting everyone to be available and responsive during the same daily window of time.

3. Use (a)synchronicity to your advantage.

At some point, we’ve all left a meeting with the same feeling: this should have just been an email. In truth, an email isn’t enough, but it can turn an hour meeting into one that’s over in fifteen minutes.

There’s a story, beloved by the startup community, about how Amazon holds “silent meetings” that begin by reading a six-page memo that narratively describe the idea or problem under discussion. There’s many aspects of Amazon’s culture that should be avoided, but this one is actually pretty good. It maximizes the advantages of writing and speaking while minimizing the disadvantages of each.

Writing helps articulate your argument, instantly share it, and affords consideration and thoughtful response from readers. Meetings are a great way to synchronously communicate, build consensus, and create opportunities for dialogue and debate. Try to use each to its greatest advantage: don’t introduce new ideas in a call, and don’t expect an immediate response in writing.

Another way to successfully combine writing and meeting could be to speed up a morning stand-up routine. Having everyone write up what they’re working on massively speeds up the process, so that you can focus on discussing blockers and how to overcome them.

4. Don’t backchannel.

Backchannelling fractures and fragments understanding, like looking at your organization through a broken mirror. Nobody is able to see the whole picture, just shards that look different based on their perspective. Keep communication out in the open as much as possible, whether it’s by email, chat, voice, or video. Direct messaging should only be used for “closed-door” situations: providing feedback, expressing concerns, and planning surprise parties.

While it may feel more immediate and secure, these are false positives. It’s no more immediate than sharing the same information in a public. As long as the information being shared isn’t personally private, trust your team to be able to handle it. Tools like Slack and Discord use “channels” to help keep conversations on-topic—channels often provide enough focus to keep the conversation on a need-to-know basis without making it secret, and allowing employees to opt-in to discussions on their own. As you solve problems out in the open, you’ll build build understanding and consensus.

5. Call freely; decline freely.

Talk is cheap. It’s also information dense, synchronous, and empathic. Getting into a habit of simply calling someone when you need to think through a problem can be a powerful force-multiplier. But feeling pressure to answer every call can destroy your focus and productivity. Create an understanding that it’s up to the receiver to answer if they have the time and attention to. If it’s really important, call again. If it can wait, call back or fall back to a more asynchronous mode.

Tools like Discord, Slack, and Teams provide flexible audio/video channels for jumping in and out of quick conversations. The power of a simple phone call shouldn’t be overlooked. Voice memos and voice mails can be easily substituted if you just want to give a quick report. The point is that you’re actually talking to one another like actual human beings, not just typing at one another.

6. Chat is a watercooler. Don’t lean too much on it or things will get messy.

Chat is hard to search, hard to follow, and hugely distracting. It’s a bad format for building shared knowledge and a bad medium for synchronously communicating. When use chat, you let your thoughts guide your speech. Many ideas require more development, more editing, and a slower pace than chat affords. Yet, it’s come to dominate remote workplace culture because it’s so low friction.

Chat works best as a social glue, facilitating low-stakes discussion, scheduling, and sharing for things like quick status updates, dropping interesting links, and sending photos of your pets. Never expect somebody to instantly reply to a DM or a chat, treat it as the lowest-stake mode of communication (see rules ##1, ##3, and ##5). Any important information—a company policy change, or an important deadline—needs to be communicated outside a chat (ideally, as a memo or a meeting, depending on the urgency).

7. Prioritize spending time together, in-person and on-line.

Remote work is inherently isolating. It often involves closing yourself in a quiet room and endlessly looking at your computer. Sociologist Ray Oldenburg calls work the “second place” where people spend most of their time socializing outside their home. Employees suffer when their second place vanishes into the cloud, especially after their “third places” have already disappeared.

Creating spaces and times to socialize and gather, even through a video call, are essential for building the culture of a remote workplace. Bots that schedule random coffee chats can encourage coworkers to better know one another, while making space in the day for conversation and downtime. Incorporating a creative prompt into a daily stand-up routine can introduce spontaneity into an otherwise rote process. An occasional lunch talk, happy hour or game time can gather everyone for low-stakes, informal hangout (as long as it’s within the office hours established as part of ##2).

8. ‌Managers must lead by example.

This rule applies to the least number of people, but is no less essential. None of these guidelines will work if the people in charge are shooting off 11 p.m. emails that demand an immediate response, feel insecure when their calls go unanswered, and talk shit in DMs. If you’re a manager leading a remote workplace, establish guidelines, follow them yourself, and constructively reenforce them. Managers set the example, reinforce the culture, and have the power to spoil a healthy culture or reboot one that’s crashed.

Remote working is amazing, as long as its under the right conditions. This isn’t an exhaustive list, and may need to be tweaked and adapted for the particulars of the remote workplace you find yourself in. These principles have, however, helped me to guide frustrating conversations towards constructive outcomes, create a shared sense of purpose, and protected my most precious resource: uninterrupted focus.