How to not suck at remote working

I’ve been trying to work remotely (from home, in my case) since the moment I had my first job. I’m not sure why exactly, but I just wasn’t made for the 9 to 5 office life.

I dislike everything about working in an office. The daily commute, the empty conversations, the distractions and of course the meetings. But on top of it, my productivity never peaked when working in an office environment. I only showed up to clock my eight hours, then went home to do my “real” creative work. Often I didn’t even do anything at the office, just pretended to be busy before I could finally call it a day at 5 p.m. That was about 14 years ago and things have changed quite a bit since then.

Today, remote working seems to be more popular than ever. According to a recent survey from Gallup, 43% of employed Americans have worked remotely in some form over the past year. Other reports state that by 2020, 50% of the American workforce will be working remotely. Some because they want to, some because they have to.

And it makes sense. Working remotely, if done right, is a win/win situation for everyone involved. According to this study, given the choice of a 10% raise or the option to work remotely, 53% of all participants chose to work remotely instead of getting the 10% raise. Dropping the commute is by far one of the biggest factors of increased happiness for those who made the jump. Even if your commute is only 30 minutes it makes a huge difference; the influence it has on your overall mood and happiness is enormous. There are few things people hate more than their commute.

Other benefits of working remotely are a more flexible working schedule, and typically a lower cost for the company that employs you (they don’t need to provide office space, etc.). The positives are fairly clear for both parties, at least on the surface.

Yet, I’ve learned that while working remotely is appealing to many people, very few are good at it. Most people I’ve worked with remotely are distracted, unproductive and certainly not performing the way they should or even want to. The remote life is not easy and you have to learn how to do it right.

These are the rules to live by if you want to be a successful remote worker, at least from my perspective.

#1. Know who you are

Although some might say “remote working is the future,” I don’t believe this is a general truth. It simply doesn’t work for everyone.

For one, working remotely can be pretty lonely. Some need the daily watercooler conversations and a tangible feeling of belonging. This may exist to some extent within a remote team, but it’s inherently different. For example, your Slack chat may help replace the daily watercooler conversations, but it’s not the same as sitting down and sharing lunch with your coworkers.

Some people, given the chance to work from home, would not accomplish anything because they’re easily distracted or simply need the fixed schedule and structure of office life.

Ask yourself:

• How much do I value social interaction throughout the day?
• In what specific ways could I create a healthy social balance as a remote worker? Would that be enough?
• How much do I value and depend on the structure of an office environment?

I’ve worked with people who were two completely different personalities when working remotely compared to working in an office on location. Be honest with yourself about who you are and what you need before jumping into remote work.

"There is nothing more toxic to a remote working environment than people who make assumptions."

# 2. Over-communicate

This is by far the most important practice of a successful remote worker. You have to over-communicate, almost to an extent where it feels like you’re talking to yourself out loud.

The challenge with working remotely is that you don’t really know what other people on your team are doing. You can’t just walk over and check in with them at their desk or exchange a few words over lunch. To sync up remotely means you have to schedule a call or bother them via chat, and you can’t just have meetings all day to make sure you’re caught up with everyone.

My biggest frustration when working with people remotely is when those people do not communicate — folks who don’t ask any questions, who don’t tell share they’re doing or what they have accomplished. It’s easy to fly under the radar and disappear when working offsite; you have to actively fight against it.

The most damaging are those who make assumptions — assuming that someone will do something about X or will get in touch about Y. There is nothing more toxic to a remote working environment than people who make assumptions:

“Oh, I didn’t reply to that email because I assumed you would do it.”

“I assumed you would get in touch with me if you needed something.”

“I thought you already did that.”

“I thought this wasn’t as important, so I didn’t do it.”

Remove assumptions. Over-communicate and be proactive about it. Reach out immediately and try to inform people about what you’re doing as often and as efficiently as possible. That doesn’t mean you need to schedule dozens of meetings, but a simple message in your group chat such as, “Hey team, today I’m going to work on X. Just FYI,” puts everyone on the same page and gives people the opportunity to jump in if needed.

Over-communicate everything: What you are working on, when you think it will be done, if you’re running behind and how much you’re running behind. Even if people don’t respond to your updates, you need to be consistent about it. Just because someone didn’t acknowledge your update doesn’t mean it’s worthless — quite the opposite. It means they feel informed and satisfied about your current status.

I love working with people who speak their mind as openly as possible, people who proactively reach out about everything and don’t shy away from bothering someone if they think it’s important. The worst thing that can happen when working remotely is that you work on something for an entire week, only to find out that everything you did wasn’t at all what your team was expecting you to do. Over-communication helps set expectations. And as a bonus, it helps you manage your time better, since keeping your team informed requires you to stay on top of your to-do list.

# 3. Use The Daily Status Update

Yes, the third rule also relates to communication. It’s that important.

I try to have relatively few meetings when working remotely. I don’t like calls and I think they’re time wasters for the most part. I do schedule calls with my team every other week because they boost morale, and a little bit of chatting certainly helps you build relationships with your team (some people need this more than others, and I’ll admit I’m low maintenance when it comes to social interaction). But most days, I like to be efficient and productive. After all, that’s the reason I decided to work remotely.

But there is one practice that has been incredibly effective for me: The Daily Status Update. It’s a simple email sent at whatever time you end your day. This status update follows a few rules which are as follows:

You’re not allowed to spend more than five minutes writing this update. It should be efficient, and spending more than five minutes writing a status update would defeat the purpose. By imposing this time limit, you will focus on the most important details and your status update won’t be a nightmare for others to read.

My remote team uses a set format and template for this status update, which looks like this:

What I’ve worked on today

• Something I did
• Something else I did
• Another thing I did

What I will work on tomorrow

• Something I want to do tomorrow
• Another thing I want to do

Where I’m stuck

• Need help with XYZ

Every day you take this template, add your bullet points and send it to your team. Since you’ll only be spending five minutes max, it’s an easy addition to your daily routine.

These three headlines work wonders for you and your team’s productivity without having any meetings whatsoever, especially when working across time zones.

By sharing what you worked on today I know what you’ve accomplished without having to ask. Seeing your “tomorrow” list lets me know that you have enough on your plate to be busy tomorrow, plus I can plan my own work around your tasks. Worst case, I can jump in and say, “Hey, I saw you want to work on this tomorrow, but can you work on this other thing instead?”

The third list in your Daily Status Update email is the most important: The list of what you’re stuck on or where you need help. If I, as your manager or colleague, see the same task under “What I will work on tomorrow” and “Where I’m stuck,” I know to jump in and help you with whatever you need so you’re not roadblocked for tomorrow. This is one reason why your status update needs to be sent every single day. If I continue to see a team member putting the same task under “Where I’m Stuck,” I know something is wrong.

P.S. I always encourage people to link their status updates to the work they’re referencing. Dropbox links, images, to-dos in Basecamp — link to it so I can easily get more context if I need it. This will save time for both of us.
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Knowing who you are, over-communicating and having a structure for how you communicate are in my experience the three main ways to become a successful remote worker. If you do these things right, everything else will follow.