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3aaa208 Aug 12, 2017
@lenazun @puzzlement @tehpeh @slant @guih @crowchirp @bitbckt
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Working remotely

Working remotely sounds great. We think we’ll save ourselves the commute and we’ll be able to flexibly weave in and out of work and home life. In reality, work takes a different shape when there is no office, and we’re all in different environments trying to connect to other humans.

We have no “central” office at Hypothesis and we currently work from 4 different countries in different time zones. We have learned that communication, decision making, social interaction and leadership need slightly different strategies. We still have much to improve, but we’re working on it every day.

Feel free to share this content under a CC license. Send a pull request with your edits and ideas!

These are some of the things we’ve learned while working remotely:

Before you get hired (some questions to ask)

Before you start working remotely at a new organization, you should explore how they structure remote working and if there are any expectations mismatches between you and the organization. A particular remote job may or may not be a match for you. This should be talked about at the time of the interview, ask as many questions as you can.

  • How long have there been remote workers for? Is the organization new to having remote workers or has it had remote workers for a long time and bedded down a remote working style?

  • What is the remote working culture like? Is most collaboration over email, text chat, phone, video conf, or some other means? Are there watercooler-equivalents like social IRC channels or video chats? How active are they? Are remote workers mainly working from home or from co-working spaces? Are there occasional team gatherings to meet colleagues in person, and are they optional or compulsory? If the organization has a very strong culture of in-person meetings, and decisions are made in social gatherings, it will be hard to integrate as a remote worker.

  • How many remote workers are there at the organization? What percentage of your team are working remotely, what percentage of teams you will work closely with are working remotely, and what percentage of employees overall are working remotely? Working as one of very few remote workers for an organization where most of your colleagues are in an office is different from a mostly or fully remote organization.

  • Are the remote workers spread across multiple timezones? If so, are your team and closest colleagues in your timezone or another one? Are you expected to adapt your working hours to overlap better with your colleagues? How are meetings and other commitments scheduled across timezones? You will want to know what the expectations are in terms of their working hours and availability.

  • What are the benefits for remote workers? Will the organization reimburse any of your remote working expenses, such as membership of a co-working space, home office furniture, or your home Internet connection costs? If you're working in a different country from most of your colleagues, will you get equivalent benefits to your colleagues (eg, health insurance coverage)?

  • What are the travel expectations for remote workers? Are you expected to travel to headquarters or other offices or customers, or to team meetings, and if so, how often and for how long? What are the travel policies and allowances for remote workers? How do these travel expectations compare to those of non-remote colleagues?

  • What are the career progression possibilities for remote workers? As a remote worker in a partly non-remote organization, could you move into more senior positions over time, such as team leader, middle manager, or executive? Could you move into other teams in the organization, and if so, which ones? Are there some roles that are closed to remote workers? Match these answers to your own career goals.

  • Is there support for first-time remote workers? If you haven't worked remotely before, will the organization support you in learning how to work remotely, and if so, how?

  • How do remote workers get coaching, participate in pairing and learning opportunities? If you're at the start of your career, remote work may be particularly difficult. You may need a lot of support and guidance from more experienced team members, and this is not easy to do remotely. If you're a bit more advanced, you still should ask how these learning opportunities and collaboration spaces are happening for remote workers.


  • Read, write everything down, repeat. Working remotely will require you to write and read much more than you think. Write your thoughts, explain how you came to a conclusion, propose a solution in writing. Your input will be required in writing too, and there’s a number of emails and documents that you definitively need to read to keep up with what’s going on. You will find yourself repeating things many times, in different documents/meetings/chat rooms, and that’s ok.

  • Rules of polite communication are not the same. Sometimes you will have to interrupt people, hijack a meeting, reschedule at the last minute, ask people to repeat themselves etc. You still get to be nice to people, say thank you, please and sorry, say “good morning” and “have a good evening”.

  • Interruptions are OK. Don’t be afraid to ask people if they have a minute. It’s on the recipient to manage their time and availability (i.e turning off their slack notifications, or saying “sorry I can’t right now, I’m on a call”). Don’t guess on other people’s availability, just ask.

  • Be direct. Don’t “ask to ask” or bury your request in a full paragraph. Lead with your request or question, and provide a format for the response you want (yes/no, comments on a document, +1s or -1s, etc). Keep your sentences short, you don’t need to heavily justify everything you say, we believe you!

  • Don’t read too much into things. Don’t interpret lags, non-responses, silences, missed events, short emails, dropped pending items, cut-off chat conversations or distracted interlocutors. Chances are these are incidental communication issues, not intentional messages.

  • Plain, human language. No one should be furiously googling the word you just said. Try to keep the jargon out of our group conversations: jargon tips the power balance and alienates people. If you don’t know what X is, please ask immediately, even if you just need a refresher.

  • Informal conversations, chats just for the LOLs, are OK. It’s also OK to politely decline if you’re busy. This is awkward, but it’s the only way we can have informal conversations when we’re not in the same room. It’s perfectly fine to chat about music, puppies, breakfast and animated gifs. It’s fine to make jokes in conference calls. HAVE FUN.

  • Response lag. Do not expect an immediate response, and don’t feel pressured to respond immediately, unless something is on fire (in which case we will have an appropriate way to ping you). Give people time to switch context, think, and process. If you need a quick response, please indicate that in your request (i.e. “I have a meeting in 1hr and I need your thoughts on this” or “whenever you get a chance before the end of the week”)

  • Asking questions. The earlier you ask a question, the happier we’ll all be. Don’t struggle with a problem or a doubt by yourself, just ask someone. It doesn’t matter if they look busy (remember, it’s their job to manage their own time). Ask detailed questions and give indications of the type of answer you’re looking for (an idea, step by step instructions, help troubleshooting, debugging, testing something out, etc)

  • Communication style. When you’re working different hours in a different place, co-workers have no context for how your day has been or what mood you’re in. Maybe it’s too early in the morning and you didn’t sleep well. Maybe it’s been a long day of chasing an annoying bug. Take deep breaths, be aware of your emotional state, be as positive and open as you can be. Practice empathy, ask how other people’s days have been, try to understand context and assume the best.

  • Isolation. Everyone who works remotely at some point feels isolated, out of the loop, or trying to catch up with what’s going on. You will have the vague feeling that discussions, decisions and important things are happening elsewhere, and you’re missing out. This is most likely not true. The only way to find out is to raise the issue, ask how things are going, ask your manager for general org update.

  • English: not everyone’s first language! Be compassionate and forgiving, but don’t be afraid to correct us nicely (this helps us, seriously). We will do the same with your Hindi/Spanish/German/Irish/others. Here’s a great guide on how to do this.

Schedule and time management

  • Individual time management. You’re responsible for your own time. This is extremely important. You get to define when you’re available and when it's OK to contact you. You have to accept/decline meeting invites, set up the appropriate reminders, set yourself away on the shared calendar, snooze your Slack notifications, and plan for your week/day. You get to decide when to switch contexts. No one can do this for you.

  • Calendar invite etiquette. Provide context for all meeting invites (perhaps have a little chat with the people you’re inviting before sending it). Make some attendants clearly optional, if they are. Include the meeting main goal on the invite, and if there’s an agenda or supporting documents, include links to those too. The default for a meeting should be 30 minutes, consider if you really need more. Send notifications if you need to reschedule a meeting or cancel it.

  • Avoid expensive meetings. Think about the minimal set of people who should attend a meeting, and what their role or input will be. Is this something that can be communicated via email? If a recurring meeting keeps being canceled, maybe you should rethink the need for that meeting or its frequency.

  • Scheduling across timezones. Define a time band for meetings on your day. What is reasonable and acceptable? Use the Meeting Planner if you need to find a good hour to meet. You can also use the “find a time” feature of Google calendar. Finally, ask if it’s possible to reschedule a meeting that is outside of your work hours, or if someone else can attend on your behalf. Don’t expect others to worry about your time (remember this is your job).

  • International holidays. We have an approximate list of international holidays on the countries where our team usually live. The general rule is: if the holiday is on the list, we don’t expect you to be available. If it’s not on the list, but it’s important for you, let us know in advance and take the day off (put it in the team calendar). Team meetings where the 30%+ of participants are on holiday will be rescheduled.

  • Etiquette during meetings. Start max 5 minutes after the starting time, maybe other people need pings and reminders. Remember Gunner’s rule: In a group of n people, try to talk 1/nth of the time. Keep the agenda in mind and mentally check what points have been covered, and what is yet to be discussed. Don’t be offended if someone else mutes your microphone during the meeting, you may not notice the background noise. Our meeting time band is very limited and chances are your participants have other calls on the hour: finish on time (or early!). If there was not enough time to finish a discussion, make sure you follow up.

  • Block time on the calendar. We have an open vacation policy but we often have to remind people to block time off not only for vacation but also errands, travel time, mental health, reading and studying, feeding the baby, walking the dog, picking up the kids, taking your mom to an appointment. Any time you need without interruptions should be blocked, we don’t need to know why.

Decision making

  • Communicate your ideas as proposals. In a collaborative team like ours, there’s a ton of ideas popping up. We love discussing, playing with ideas and imagining the future. It is helpful to say “we’re just playing with this idea” or “we’re thinking about doing it this way”. Make sure you sound like you’re clearly making a proposal, and not a demand or a decision. Do not expect these discussions to result in concrete actions, because...

  • Decisions should be communicated via email. When a decision is made, communicate it clearly as a decision via email, with clear next steps. Technical decisions have their own documents (ADRs). Do not assume Slack is a good record for decisions or a good way to assign responsibilities. Work is assigned on cards on a sprint, github issues, in a face to face conversation, or via email.

  • Communicate your opinions. When you send an email analyzing a problem or presenting different options, it is useful to clearly say which one you prefer. Don’t just set up a general debate and hope people pick it up. If you say “My preference would be A”, people have a starting point to agree, disagree or ask questions.

  • Feedback and suggestions. If you need people to weigh in or review your work before a specific time, make it explicit in your request and set a reasonable deadline. Also, be specific on the type of input you’re looking for. If you’re giving feedback, make concrete suggestions. Understand that not all your requests or suggestions will be accepted.

  • Meeting notes and action items. Retrospectives and post-mortems must have notes and action items. Other meetings can have notes, preferably taken collectively in a google doc, not always by a woman, or the youngest person in the room, or always the same person. Action items should, preferably, have a responsible person who will follow up.

Leadership and group dynamics

  • Assume everybody is doing the best they can under the circumstances. It’s hard to trust and rely on other people if we haven’t met them in person, or if our contact is limited. We have to make an effort to assume people are doing the best work they can do at the moment. We have to believe that any mistake or omission is made by a person who is trying their best, dealing with a set of variables we may not understand, and act accordingly.

  • Make room for the quiet voices. Some people need more time to think and process before speaking, or are overwhelmed in large conference calls and in-person meetings. Some of us need to double check our words (if English is not our first language, or we’re working outside our area of expertise) . We have to make an effort to ask directly what the quiet people think, give them plenty of background material before a meeting, and allow space to submit their thoughts in writing. Make sure others don’t interrupt or shut down the quiet voices and acknowledge their contributions.

  • Learn to facilitate discussions. If you’re a leader, you will be playing facilitator more than a participant in most discussions. Learn how to balance different points of view, keep track of time, keep discussions on point, make sure there’s notes. Even if it’s not your meeting, sometimes you have to step into the role, so be prepared.

  • Traffic control for topics and discussions. If a discussion becomes too large or goes off topic, find a way to split it and send it to the appropriate channel. “This could be better discussed by email” or “let’s take this to a slack group” or “let’s have another call for this other topic” are good things to say. Intervene when discussions are going nowhere or becoming dialogs. Don’t let people get into a pointless argument, it’s usually easy to see (from the outside!) when a discussion is not going to end well.

  • Apologize explicitly when a mistake is made. Over-communicate around mistakes and make sure affected voices are heard. Have a post-mortem or a learning session, copy the team on the results and action items. Get in the practice of acknowledging conflict or misunderstanding: when you are all remote, there is no way to know who’s mad at whom and who solved their issues. This can be toxic in the long run, it’s better to speak frankly about what’s going on.

  • Recognize good ideas and actions. Give credit for good ideas. Celebrate team and individual accomplishments. Have a symbolic token of appreciation (we have a couple of animated gifs for special occasions). This is much easier to do in person, but we have to be even more intentional when we’re all in different places.

  • Intentional 1:1s. Most of us have weekly 1:1s with our manager. You can schedule a 1:1 with anyone on the team at any time, just ask! These 1:1s are much more productive when they are structured and have a theme. For example, “this week we’ll talk about how we’re doing on quarterly goals” or “this week we’ll give each other feedback”. Some of us keep a running document where we write down notes, so we can review what we talked about last week.

  • Giving each other feedback. If you’re comfortable with giving direct feedback to someone, phrase it as “things you’re doing well and hope you continue doing” or “things you could be doing better”. We do a round of peer and manager feedback twice a year, but "in the moment" feedback is even better. When you receive feedback, listen and be appreciative. Keep in mind that the good things you’re doing outweigh the things to improve.

  • Your words matter more than you realize. In a small team, what you say matters to everyone on the team. Your words will be remembered and interpreted, as well as your tone and your mood. This is especially true if you’re in a leadership position. Working remotely makes this even trickier, because people will have few opportunities to interact with you.


  • The world is loud. You will need a quiet place to work, at home or elsewhere. Coffee shops are not the best. Libraries are OK, but you need a private room to make calls. A good pair of headphones, a functioning webcam and a good audio setup are essential.

  • Light is important. Daylight will make you happier, and it will make for better conference calls. Exposure to light during the winter is even more important.

  • Traveling and working. Think in advance of your setup, your availability, your internet connection etc. Let people know you’ll be traveling and adjust your schedule.

  • Are you OK? Sometimes we’re caught in the middle of emergencies and chaotic situations. In these cases, your only responsibility is to be safe. If it’s at all possible, send us a signal saying you’re OK.

  • Flaky internet connections. They happen, and they will frustrate you to no end. Disconnect your webcam and close other processes in your computer that may be using your bandwidth at the time of a conference call. If you attempt to join a meeting and it fails a couple of times, just apologize, reschedule or skip. Have a phone number as a backup plan.

  • Coworking spaces. You are welcome to find a coworking space and discuss with admin the details of pricing and reimbursement. Many co-working spaces only have an open floor plan, make sure you’ll have a quiet place to make video calls.

  • Find a good ergo setup. Notice if you need a special keyboard, a larger monitor, a better chair. All these things will make your life better in the long run. Make sure you make arrangements to adapt when traveling.

  • Don’t forget to eat, sleep, talk to people IRL. Work can be too interesting, too consuming, and you may be tempted to skip meals or go to bed late. Please don’t! You’ll be more pleasant to work with if you’ve eaten, had tea/coffee/etc, have talked to other people who have nothing to do with work, and have slept and dreamt happy internet dreams.

Health, family and the real world

  • Define a routine. My younger self would hate this suggestion, but it’s really useful. At the start of the day write down what you expect to be doing at approximately what time. Set some time to eat, stretch, go outside. Plan for a time when you will stop working. At the end of your day, make a summary of what you’ve accomplished, send it to #standup, and consider your workday finished. If you’re still working late at night, Lena will send you a creepy moon face emoji to remind you to log off.

  • Take the weekends off. This is very important. We don’t expect you to be available on the weekends and we’d rather you have a good story to tell on Monday.

  • You can share your personal life with us, but you don’t have to. Some of us like talking about our families and our lives outside work. Don’t feel pressured to share anything personal, we’ll like you just as much.

  • Caring for yourself and others. Do not apologize for prioritizing the care of your family or your own well being. Others won’t see you every day and we’ll rarely have context for what you’re going through. We hope you feel comfortable to have a conversation with your manager when you’re struggling with a personal issue. If you don’t, let’s fix that. If you’re sick, Dan will sometimes send you soup!

  • Avoid burn-out. Learn to recognize burn-out and how to avoid it. We want you to be a happy, productive person for a long time. If you recognize the signs of burn-out on a teammate, reach out and ask how they’re doing.