The Art of Working Remotely

The Nylas team has offices in SF, NYC, and plenty of remote workers in between. Here, we share lessons in successfully working remotely.


Working remotely is a skill. It’s not hard, but it’s full of nuance and takes genuine effort. The benefits are numerous, as are the potential pitfalls. You can be as effective remote as you are co-located. All it takes is deliberate awareness, some upfront setup, a few tools, and a lot of forthright self-honesty.

When in Doubt, Say More. When Not in Doubt, Say More.

Communication breakdowns are the biggest causes of remote work not panning out. Those breakdowns are generally caused by a mix of environmental, psychological, and sociological factors. Just about every section of this guide addresses this fundamental issue one way or another.

Make Extra Sure You Can Make Daily Check-in Standups & Meetings

Nobody knows you're being blocked until you say something about it. If people said "how are you doing" as frequently in chat as they do in real life, status reports may be less necessary. Status updates are a remote-equivalent to "how are you doing". When asked IRL we tend to include both life and work things. Don't leave out the life things in the remote version.

Leave Continuous, Passive, Digital Breadcrumbs

When co-located a lot of information is conveyed when people glance at your screen dozens of times a day. It's a 1/2 second mini-update of what you're working on. Those mini-updates are crucial. They're mini-affirmations we're all still working towards the same goals together. They're mini doses of self-accountability for fear of randomly being on-looked at. The remote equivalent is all of the notifications when you review code, or update a project tracker, or commit something. As long as the notification systems are sufficiently passive, properly scoped, and require < 1/2 second of attention, they provide a similar effect. In the real world, scoping is provided by the physical proximity of your team. In the remote world scoping is provided by Slack channels and filtering systems.

Be Visually Present & Aware of Other's Presence

A team is a fundamentally visual thing. Seeing each other invokes a lot of subconscious processes. If you can't see someone, you'd be surprised how fast you jump to the conclusion that they're not working and not with you. Passive, visual presence is surprisingly important. It is the strongest form of the "I'm available" status. We use the Google Hangout wormhole to emulate this as best as possible. It's also a powerful self-accountability system to know your teammates can see you. It's a subtle but powerful reminder that you and your work are needed.

Finding a Good Workspace is Deceptively Hard.

Take a look at these workspace requirements. Missing any one can have disastrous effects on productivity. How many times have you heard/said: "I can't talk here", “The internet cut out”, “Battery is about to die”, “Too much background noise", "Can you hear me now"? These may seem like trivialities, but they have serious repercussions on communication activation energy, focus, flow-state, time & money.

  1. > 80% chance of finding a seat
  2. Ability to take a call at any moment with the proper equipment:
    • Background noise-canceling microphone (not your computer's microphone)
    • Headphones
    • < 40 dB ambient environment (quiet voices)
    • Can talk freely without feeling rude
  3. Good enough internet: - Frustration caused by a choppy video link can't be overstated. It destroys any inclination to use the highest communication-bandwidth medium you have.
    • Download Internet speed > 10Mbps
    • Upload Internet speed > 5Mpbs
    • Latency < 200ms
    • Uptime > 95%
  4. Power outlet - If you're less inclined to jump on a Google Hangout or Slack chat because you're afraid of running out of battery, then this is now negatively impacting you.
  5. No time limits (wifi or seat usage)
  6. Comfortable seat

The litmus test is simple: "Does this place make you feel less inclined to jump on a quick video chat?" If yes, then your environment is taking a subtle but significant toll on your effectiveness and productivity.

Surprisingly few places fit all of the requirements.

It's a poor assumption to think you can go anywhere and find a spot to work. Most places are lacking on several fronts and cause compounding subtle stresses over time. 

For a full day's worth of productive work you either have to really know a good place you've been to a bunch, or should just invest in a day-by-day co-working space (there are so many now)!

Think about how much you're paid-per-hour-equivalent. Multiply that by the efficiency difference between a dedicated working space with all of the above requirements and most coffee-shops. Almost always it's an economic no-brainer.

Thinking of the time-value of money — The $100/hr heuristic.

Finding a new coffee shop:

  • 10 minutes of Googling/Yelping ($17)
  • 5 minutes of teardown/cleanup ($8)
  • 15-30 minutes of transit time ($25-$50 + $3 of subway or + $10 Lyft)
  • 5 minutes of ordering coffee/setup ($8 + $4 for coffee)
  • 5 minutes of fiddling with wifi/finding a seat ($8)
  • 10 minutes of not-really-working while waiting for a better seat to open up ($17)
  • 5 minutes of moving again ($8)
  • 15 minutes of spooling back into working context. ($25)

TOTAL: 70-95 minutes. ($110 - $160)

Now imagine if after all that the coffee shop was full and you had to do it all over again!

Make "Working Time" and "Not Working Time" a Binary Thing in Your Head.

It's completely fine to not be working from 1pm to 4pm, but just be honest with yourself about that time. Half-working is double-shitty. It 1) Detracts from your focus and prevents "Flow", and 2) Tricks yourself into thinking you're being productive. We, and many others, don't believe there exists such a thing as "Multitasking".

Being in a co-located, open-floor plan office naturally makes it feel slightly weirder to be in that mixed state. It also (perhaps unfairly) makes it weirder to have not working time from 1pm to 3pm.

The simple remote-equivalent is to passively post in Slack when you're coming off and on (self-accountability again), or use your presence on Slack as your proxy for "current status". (just be consistent about it).

Make "Not Working Time" Known. Make "Out of Office" Not Ambiguous.

"Out of office" is ambiguous. Are you seeing a doctor? Are you scuba diving? Are you sick? Are you working from a co-working space in Metropolis?

When you're co-located it's pretty obvious when you're not working — you're not there. When you're remote, you can't use that same metric (save quantum effects).

Make it explicit. Say the hours you'll be available (remember timezones!). Say if it's a working day or an off-the-grid day. There is no "in between".

This serves several beneficial purposes. It lets your team know when it's more acceptable to ping you, it gives yourself more accountability, it saves everyone from a "is he working" angst, and it also means your "off-the-grid" days can genuinely be "off". Don't make us enforce a minimum vacation day policy!

Get Good at Timezones

Especially around daylight savings time switches. PST = -8 UTC but PDT = -7 UTC. Europe and the US switch DST on different days. Wolfram Alpha is awesome at conversions. Hot-key it.

The "Laundry Effect"

When you're working from home, it's so, so tempting to do laundry.

Imagine if I scheduled a 10 minute meeting in the middle of the day, then after you got back, and just about when you started to hit a Flow state, I scheduled another 10 minute meeting. Finally, just for fun, I'm going to tack an extra 30 minute meeting on the end of the series.

Set boundaries to prevent you from doing this to yourself. You'd kill a manager if they did that to you. This is one of the literal/metaphorical reasons I rarely work at home.

Invest in tools

Communication activation energy is everything. Distributed work tools are competing with the co-location equivalents of verbally saying something or making furtive glances in one's direction. Getting your tools tuned such that everything is a single click or glance away is surprisingly difficult.

When in doubt, use the highest communication bandwidth available (aka the power of video)

Communication bandwidth is about as measurable as digital bandwidth.

  • Typing: 60 wpm
  • Voice only speaking: 200 wpm
  • Reading: 400 wpm
  • Visual gestures + speaking: (way more then 200wpm)

The "information density of gestures" is a hot and highly debatable topic of research in psychology & business research. It doesn't take a lot of academic papers to tell you that it's high. Very high. When a group of people are co-located around a table it's the microexpressions of affirmation, trepidation, or disagreement that pushes some ideas thorough and tables others.

Without video, all of this is lost. This is why video quality (and digital bandwidth) matters. If you can't tell the difference between a genuine smile and a Duchenne (aka fake) smile because of pixelation then you're losing a ton of information.

This is also why working environments have to support video (noise, bandwidth, microphone hardware, etc), and why it's so important for video tools to be low-activation energy.

Make it trivial to pair program (use Hangouts Screenshare or tmux)

Don’t be shy to setup a quick screenshare for some pair programming. For those that like more configuration there are plenty of solutions with tmux, ssh, and others (including Atom).

Make it trivial to video chat (Use Hangout wormhole for persistence)

Use one of our persistent Google Hangout rooms (/standup etc). Make it so that talking to someone via video chat is as easy as possible, ideally a single link click. Slack video is pretty good at 1-click calling. So is pasting a semi-static Google Hangout link.

The conference rooms that have Hangout boxes use semi-permanent names. They should be logged into them at all times.

Make it trivial to draw ideas (use document camera + Hangouts + print screen)

This is an area that doesn't have many good web-based solutions -- though there are document projectors/cameras. Get one of these then point it down at a table surface from 2ft up. Then draw on real paper and screenshare the results across a Google Hangout. You can then take a screenshot and paste the auto-clipped Dropbox link into Slack or put the actual file in Dropbox.

Explicitly ramp-up Slack usage

To re-iterate a theme: when in doubt, say more. When you're co-located you can verbally say "hey you". Think about the number of times you do that in a given day. When working remote each of those instead has to be a Slack @mention. 

Reading is 10x faster than typing. Skimming is even faster. (video chat is faster still). Having too much to read is never (yet) the problem. Not typing enough is far, far more likely to be the greater issue.

Treat Slack like you'd treat a physical room. Your brain is naturally very good at filtering passive information. This is why you can hold a conversation in a room with lots of people talking. This is why you can so effectively drop in on different conversations going on at once. This is why it's okay to have a lot of activity on Slack across all net channels.

Explicitly ramp-up usage of other collaboration tools

This is related to the "digital breadcrumbs" and "status reports" concepts. When remote it's very difficult for others to get a sense of what you're doing. Being extra explicit and accurate about Phab tasks, and other tracking systems goes a really long way to making them reliable indicators. It also has this side effect of making project progress more rigorous and efficient.

Explicitly be more thoughtful on commit messages / status updates

When co-located there's a very strong tendency to write semi-nonsensical commit messages and code review explanations with the assumption that you can turn around when your reviewer mutters "wtf". This can be mitigated by being more open to writing "wtf" on Slack and by writing more thoughtful commit messages.

Time auditing

When you're co-located everyone naturally falls into a similar rhythm. People eat food at about the same time, and you get a sense of how quickly (or painfully) someone is getting through a feature or bug. When remote these rhythms are very hard to pickup on and time dilates in weird ways. No relativity required.

Keep track of how long you've been working on something then let people know in Slack/JIRA/and any other tools you use. When you're co-located, your teammates know something is a time-consuming bug based on swears-uttered-per-hour. When remote, you just need communicate when things are getting stuck over Slack.

Other resources

There are many. Here are some:

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The Nylas Team

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