The Complete Guide to Working On A Remote Team

The secret to increasing productivity, work–life balance, and team happiness

15 min readJun 28, 2017

This is a guide for people on remote teams or those considering it. Why go remote? What are the benefits and how do you overcome the downsides? Learn how remote life can make employees happier and more productive if done right. Avoid the common mistakes and learn best practices.

What Does It Mean to Work at an All-Remote Company?

Work-from-home policies and remote workers are becoming more and more common in tech. The next wave of workplace flexibility is all-remote companies where there is no headquarters or home office. If all we need is a laptop and internet, why should it matter if we are physically in an office?

“Last year, 43 percent of employed Americans said they spent at least some time working remotely” — New York Times

I’m VP of Product at Octane AI, an all-remote company and we have a team of 15 people all working from different locations. We collaborate on video calls, Slack and Google docs. We still share jokes and have water cooler gossip, we just have no physical water cooler. Other all-remote companies include Automattic, Basecamp, Buffer, Doist, InVision, RebelMouse (where I was previously VP Product), PowerToFly, Zapier and many more.

Why We Chose to Make Octane AI an All-Remote Company

We believe the best talent isn’t in any one city. We look for the best people for our team and our mission no matter where they live.

Women make up 42% of the leadership at remote companies, compared with 14.2% in S&P 500 companies. — Fast Company

We believe collaboration can happen just as effectively remotely, if not better. We believe remote teams have all the tools at their disposal to successfully collaborate and be productive.

“There will be no ‘digital nomadism’ or ‘remote work’ in the future. They will just be cute terms that used to describe changing work trends.” — Kate Kendall, CEO at CloudPeeps

We believe performance should be measured by what you get done, not face time. In a traditional office someone can get props for staying late even if they are just goofing off. One of the benefits of remote work for productive workers AND for the company is that you are being measured by your output, not your face time.

We believe working remotely allows for better work-life balance. Because f*ck commuting. If you need to run a quick errand, run that errand. If you want to go to the gym over lunch, do it. We believe you, living your best life, will be the best for our company.

“Commuting is associated with an increased risk of obesity, insomnia, stress, neck and back pain, high blood pressure, and other stress-related ills such as heart attacks and depression, and even divorce.” —Jason Fried, Remote: Office Not Required

The Benefits of Working Remotely

Work can Fit Into Your Life Instead of Vice-Versa

Remote work allows more flexibility to fit your work into your life in the best possible way. Do you prefer to go to the gym or go grocery shopping in the afternoon when it’s less busy? Go for it! Need to do your laundry while working on a big project? I do it all the time. Since you get to choose the location and exact hours you work, you get to maximize both your productivity and your personal life.

82% of remote workers report lower stress levels — PGi Report

You Can Choose an Environment Where You Focus Best

Open-offices are all the rage for startups, but they aren’t where everyone does their best work. It can be noisy and hard to focus, leading to decreased productivity.

In one experiment in a Chinese call center, they allowed one portion of their workforce to work from home for 9 months. The productivity of those working from home increased 13% compared to the in-office group. — Harvard Business Review

As an introvert myself, I know that I focus best at home and that’s where I do my best work. We have other people on the Octane AI team who prefer to find cafes or co-working spots because that’s where they are most productive. The beauty of working remotely is you can choose the work environment that works best for you.

How to Be a Productive, Effective Remote Team Member

Collaborating Across a Digital Divide

We live in the best time yet for digital collaboration, but there are still some pitfalls to avoid to ensure you are able to communicate effectively.

“The technology is here; it’s never been easier to communicate and collaborate with people anywhere, any time.” — Jason Fried, Remote: Office Not Required

Here are some best practices:

Understand the “Why.” It can be easy to give a remote worker a task list without helping them understand the business goals behind what they’re doing. Everyone works better when they are in sync on the company vision and how their work ties into those goals. If they know the “Why” they can be a part of the creative process to help reach the company’s goals. On the flip side, if your manager gives you a task and you don’t understand why you are doing it or how it will help the company, ask!
Make sure each person has multiple tasks on their plate and is clear on their priorities. Sometimes when working remote, you get stuck on one task because you need to ask someone else about it and they are asleep because of time zone differences or are focused on something else. This is totally fine as long as everyone has a next task to turn to while waiting on feedback from someone else.
Respect work schedules when planning meetings. No one likes having to move their personal plans because of a last minute meeting. Keep in mind different time zones and try to work together to set meetings times that work for everyone. When in doubt, don’t be afraid to work together asynchronously.
Use visuals. A lot of communication in remote situations happens through text, but try to add a visual when possible. I love Droplr for sharing screenshots with drawings and text on them but other tools can work great too. Literally, if I’m referring to a share button I will add an image like this http://d.pr/i/cloUJP that points a big arrow to exactly what I am talking about. This helps make sure everyone is on the same page.
Use a project management tool. This is good advice if you’re working in-person also, but there’s no way you can have a remote team without using a good project management tool. The tool itself isn’t important as long as you can set tasks, assign them and collaborate together. Some popular ones include Trello, Asana, Clubhouse, JIRA and more.

We organize our communication and company activities around specific actions. So, instead of chatting about something that’s just popped up or sharing more ideas, we ask how we can save it for later or turn it into an action. — Kate Kendall, CEO at CloudPeeps

Use a team communication tool. You could use email but it gets disorganized quickly. I recommend Slack (which we use at Octane AI), Hipchat, Twist (a new player in the space from all-remote Doist) or a similar tool. Organize your communication in channels so it’s easier to find the information you need.
Escalate the medium, not the message. If you are having a conflict with a coworker in a text chat, don’t just continue to disagree in text. Hop on the phone or do a video call. With just text, we lose tone and body language and it can more quickly lead to a huge disagreement. If things are getting tense, get on a video call.

“At PowerToFly, we make sure that direct reports have at least one weekly video chat or voice call each week. This allows us to hear any issues that can’t be interpreted via email or group chats.” — Katharine Zaleski, Co-Founder of PowerToFly

Give people the benefit of the doubt. If they sound a bit terse, it might be that English is their second language or it might be that they had a very late night with a baby. Try to understand things from their point of view, empathy is an incredibly valuable asset in a remote worker.
Consider a team retreat. It’s not 100% necessary, but one thing remote teams do is use some of the money they save on office space to invest in a yearly team retreat. When I was VP of Product at RebelMouse I worked with some people for years before meeting then and we always worked well together, but I will say that when I did finally meet them it was an incredible bonding experience and helped us communicate even better in the future. Want advice on how to make the most of your retreat? Check out What We Learned Planning Our First Ever Team Retreat.

“Take the time to show up early to virtual meetings. I do virtual meetings both with my teammates and customers, and technical difficulties are par for the course with video conferencing technology. Showing up early makes it more likely that meetings will start (and end!) on time.” — Camille Emefa Acey, VP Customer Success at Clubhouse Software

Having a Balanced Life is Crucial to Success

One challenge for remote workers is setting boundaries between work and their personal life so they can be effective and stay sane.

Don’t work all the time. For real, this is very important. Your brain needs a break to recharge and be creative. Set up do not disturb times in slack which can let you relax and not get buzzed with notifications. Don’t be afraid to tell someone you’ll get back to them tomorrow. You having a life makes you a better worker too.

Be truly productive when you are working. Focus on using the hours in the best possible way. Setup your environment so you can focus and make sure you are clear on your priorities (otherwise ask your manager). If you work best with a separate work space from your home life, you might find yourself setting aside an area of your home to be home office or looking into nearby co-working spaces.

Team Bonding

In a remote situation you can’t all go to happy hour together or gather around the water cooler so it’s very important to still get informal bonding time with your coworkers. Some remote companies, including Octane AI, have a team retreat once a year which is great for bonding, but we also need to do it on a daily basis to stay connected as a team.

Fast Parrot in Slack, our communication tool, has become a huge part of Octane AI team culture. It’s important to have little quirks that make your team feel connected.

Here are some best practices:

Say hi. When asking someone about a task make sure you are also saying hi, asking how they are doing and generally acting like we are a team of humans, talking to humans.
Have a place for non-work related conversations. We use fun Slack channels to talk about what we’re passionate about which includes travel, working out, music, tv and movies and more.

It is my belief that working to develop a great remote working culture will pay dividends for decades to come — Joel Gascoigne, CEO at Buffer

Celebrate people’s victories with them. Victories in work or life. Props with growbot or fun animated GIFS are great for this!

“We play together virtually. Yep, that may sound odd, but some of us play online poker (it’s legal where we are). We also play video games across the internet, switch and mario kart has been a recent favorite. It’s great fun and a way to share experiences that are not just work.” — Claire Knight

Just check in with someone to see how they’re doing. It doesn’t always need to be work-related. Do be open to the fact that you might have caught them heads down on a project so don’t be offended if they aren’t chatty back.

How to Structure a Remote Work Day

People who are successful with remote life tend to either structure their day to have defined work-life balance where they have very clear working hours or go for work-life integration where they work in spurts throughout the day. Both styles of working remotely can be incredibly successful and can even be mixed and matched for one person as they need to.

“We discovered that people who work from home (i.e., telecommuting) are almost twice as likely to love their jobs than employees who work in traditional co-located work-sites” Mark Murphy, Founder of Leadership IQ

Example 1: Work-life Integration

Wake up, check slack while drinking your coffee and in your pjs. Answer a few things. Write down your priority list for the day.
Break to exercise, shower and eat breakfast
Work until lunch
Eat lunch, go for a walk to recharge or read a book
Work until the late afternoon when you are feeling brain dead.
Take a break, hang out with a friend, your kid(s), or significant other, eat dinner.
Do another bit of work in the evening when your brain feels recharged again.
Sign off at least an hour before bed to read a book or otherwise unplug before falling asleep

Tips for success with Work-life Integration

Don’t work all the time. The danger of this style is you can fall into a trap where suddenly you aren’t taking those breaks and you are just working all day. This will burn you out.
Taking breaks doesn’t mean you are multi-tasking work with other things. Humans are terrible multi-taskers.
Set boundaries with your coworkers when they ask you for stuff or set-up meetings. If they are asking for a task or a meeting in a time when you need to take a break, let them know.
Don’t work straight until you sleep. That’s a surefire recipe for insomnia.

Example 2: Work-life Balance

Wake up, drink coffee while reading the news. Go to the gym, shower, eat breakfast
Sign on and work straight to lunch
Eat lunch and maybe walk around a bit to recharge
Work until dinner time
Eat dinner, chillax, don’t check work stuff

Tips for success with Work-life Balance

The timeframe for your hours is up to you. If you’re an early bird, start at 6am and finish early; if you’re a nightowl, get started late and work late. It all depends on your ideal working schedule.
Ensure you have a work environment (home office, co-working spot, etc) where you can focus and not be disturbed.
Since you are working intensely during your work-day, fully unplug when you are not working. Use Slack’s do not disturb function or turn off notifications on your phone.
Set boundaries with your coworkers. It should be totally fine to say “I’ll get you that tomorrow” or wait to reply until your morning.

Want to be a Digital Nomad and Travel the World?

You can skip this section if you are reading this because you are working from home because of covid-19, but hopefully it will become relevant again soon!

Octane AI has had a few employees travel while working for us. One of our engineers spent two months in Japan. Rodrigo, our lead designer, recently spent two months in Europe. We think the ability to travel while working is one of the huge potential advantages of remote work. If you want to do it, working in a remote team is the best way.

Here are some tips/things to think about

Do some research and make sure you are choosing a location with reliable wifi.
Sublet your current apartment to help pay for your trip.
Look up where you’re going and make sure ahead of time you can find lodging that is reasonably priced and with good wifi so you can work.
If your working schedule is going to change, tell your coworkers in advance so they can work out any needed changes to meetings etc.
Talk to others in #travel (a slack channel we have specifically for these discussions, I recommend any remote company have something like it) about your ideas in case they have any tips. Share your photos and stories, maybe even visit a coworker along your travels, too :)
If you are thinking of changing to a drastically different time zone then please check with your manager. Some jobs will allow for more flexibility (i.e. engineering) while other jobs (i.e. account management) might require shifting your work times if you move time zones.
Going to a far-off land can be super exciting but we’ve also had people take advantage by spending extended amounts of time visiting a friend or family member.

Life Hacks and Suggestions from Our Team and You

Experiment with your most productive working hours. “Test yourself to find your best working hours. I spent several weeks testing different working schedules, and I found that I work best from 6am — 3pm. I’ve learned to do my most in-depth work in the morning and save the easier things for the afternoon when my brain is winding down. I highly suggest resources like Thrive Global or The Mission to learn about different working styles and productivity hacks.” — Kelli Kissack
Be time zone aware. “Can you find ways to be more asynchronous and inclusive of all time zones? Try to be explicit about how various communication channels are used (e.g. Slack for immediate needs, video message for standups, email for everything else).” — Bonnie Porter at Buffer
Keep up your social life. “I’d say my best advice is to not neglect your social life. If you stop talking to people face to face, it becomes harder after time. I think having live interaction every day is really important, no matter how silly it sounds.” — Milena
Look into tax benefits of having a home office. “You may be able to deduct your home office expenses. Ask your accountant (or Turbotax).” — Megan
Scope out the best coworking spaces when traveling. “When I was traveling around Europe, I would do some research and try out a few different places to work since I loved getting out of my airbnb but some cafes and coworking spaces were awesome, while others were not so great. Some had awesome comfortable chairs with a quiet atmosphere and other people also working, while other places had really uncomfortable chairs or tables. By investigating ahead of time, I could make sure I was comfortable and ready for work.” — Rodrigo
Figure out your priorities for a workspace. “Set a clear baseline, minimum requirements for what you expect from a co-working space in which you will do your best work. This helps when researching and reviewing co-working spaces and helps you ask the right questions when speaking to them.” — Keji Adedeji
Take notes and write down priorities “I love using a paper notebook for my priorities for the day and notes in meetings. I find that then when I go over my notes to save it somewhere in digital form or send to someone else I really synthesize the important stuff and focus better than if I just took notes digitally to begin with.” — Megan
Invest in a nice work setup. “I use a laptop stand for my laptop (this one if you’re curious and I don’t even get a commission if you buy it) which is so useful because some cafes or coworking spots have really low tables and you end up hurting your neck after a while so your work setup has to be great and that extra expense for a quality stand and portable keyboard is totally worth it.” — Rodrigo
Food is fuel. “Don’t forget to eat” — Milena
Get in time with the fam! “I love working remotely because it’s easy for me to go home and visit my parents in Oregon and then spend a week eating lunches, dinners and hanging out with them in the evening while still doing my job. It’s an awesome way to take advantage of our ability to work from anywhere.” — Megan
Set boundaries with friends and family. “You may need to set boundaries on people outside the company who presume working remotely means they can interrupt you anytime, or that you can drop what you’re doing or quit early, or who simply don’t realize that you are working at a full-time job with responsibilities, deadlines and other people who need your immediate attention. Even people with workplaces often goof off at them, so it’s normal for others to not realize you are “at work” when you’re sitting on your patio with a laptop and lemonade. But most will respect that boundary once they realize it exists.” — Paul Boutin

Do you work remotely? Send me your tips and I’ll add in the best ones!

I believe the future of work is going to be remote, do you agree? Let me know! Share this with your remote coworkers and let’s figure this out together.

Follow me on Twitter as @meganberry. Want to work remote? We’re hiring at Octane AI!