The Best Lessons Learned from a Year Working Remotely

May 19, 2016

This is a guest post by Benjamin Brandall, a writer on productivity, SaaS and startups at Process Street.

Remote work is one of the greatest freedoms of the internet age, but it also comes with a unique set of problems. Collaboration gets harder, relationship-building isn’t as natural as it could be, and remembering to change out of your pyjamas before rolling into the ‘office’ is something you only gradually get used to.

Thankfully, the only office job I had before going fully remote was being stuck in the backroom making cold calls to leads who couldn’t care less about what I was selling.

From the appalling management and ‘best practices’ I experienced in that role, I’ve come a long way in my first year working remotely.

Here are the best lessons I’ve learned in my journey.

Keep all communications open and centralized

Benefit of BYOD is less switching between devices

When you’re working between several different apps (project management, chat, help desk, etc), it can be tempting to do the important talking in direct messages and hide updates that would be useful for the whole team to know.

In an office, that’s like whispering vital information to someone in a meeting instead of telling the whole room.

To break this habit, we always make sure to answer in the same thread as the question. For example, if someone asks on our project management tool, ‘what’s the status of this?’, it’s useless to go on chat and direct message them the answer.

When multiple people are working on one project, communications need to be open and centralized, otherwise there’ll be confusion, hidden information and you’ll be updating individuals one-by-one when you could talk to the team as a whole.

Another example of this would be to record a meeting if someone can’t make the event. Once recorded, they post it up for the whole team to refer back to.

The mistake I made in the past was keeping my personal assigned tasks in a separate to-do list away from the rest of the company’s noise.

As much as it seemed like a good idea at the time, my boss realized it was making my work untrackable and I wasn’t updating the public task for everyone to see.

Now, I simply filter down my public tasks so I can see — in one click — what I’m responsible for.

You have to be your own toughest manager

Don't take customer feedback personally

With no-one looking over your shoulder, you’ve always got to make sure you’re eating the frog first.

Eating the frog means doing the hardest thing first — because if you eat a live frog in the morning, what’s the worst that can happen in the afternoon?

Looking at it another way, in the words of Russ Greiner: “First things first; second things never”.

Shining examples of ‘second things’ include idly organizing your filing system, refreshing social media and the ultimate form of busywork — inbox zero.

Whether it means setting repeated notifications (for some people that doesn’t help) or literally blocking your computer from allowing you on certain sites, when you catch yourself slipping into something that doesn’t resemble your daily frog, you have to be strict with yourself because no one else will.

Never delete anything

Don't waste time and effort

If you’re the owner of digital information, it’s your responsibility to keep it around even if you don’t think it’s necessary any more. As my boss asked me after a particularly bad mess up:

“What value are you getting from deleting something instead of just putting it somewhere you never look?”

This is also a valuable email productivity lesson.

Using your mail client’s archive function is much safer than trashing everything you’ve finished with because you never know when you’re going to need to refer back.

Explain tasks over screenshare videos

Screen Share

When you rattle off instructions over chat, you’re speaking from a perspective that assumes the other person knows what you mean.

You can be certain — or at least assume — that they don’t have a clue. To see things the way others see them, take a screencast.

Taking a screencast forces you to walk through the task step-by-step and demonstrate what it will look like when they do the same. As the ancient saying goes, a screencast is worth a thousand words.

The benefits of this were made clear to me when I saw the difference between having a difficult 30 minute conversation over our chat system and recording a 5 minute screencast.

While chatting, I had to send screenshots, links, and show my coworker exactly what I mean and where to click.

With a screencast video, he could see without text explanation.

From that point on, I haven’t bothered trying to explain over text and settled on just recording myself doing the task once, so in the future I even have a how-to video to send to others.

Always write processes for your work

Eliminate common problems

Working remotely, you’re not going to be able to sit down in the office next to someone and show them how to do a task they’re being trained to do.

You also don’t want to have to screencast everything over and over again!

Getting in the habit of creating a process for everything you’re responsible for will make it loads easier when you come to handing off the task. According to Zapier, the general rule is:

“Anything that needs to be done more than twice needs to be documented.”

Keep that in mind when it comes to onboarding new employees. If you’re promoted and someone’s hired to do your old job, who’s going to explain how to do every task you used to be in charge of?

If you have to suddenly write every process document and get them up to speed, that’ll be a huge hit to your productivity you could have avoided.

Obey the 80-20 rule

Save time with the 80/20 Rule

The 80-20 rule — or Pareto principle — states that 20% of your efforts make up 80% of the output.

In the late 1800s, Pareto theorized that 80% of the land in Italy was owned by 20% of the population after observing that 20% of the pea pods in his garden provided 80% of the peas!

How can you apply this to remote work? Well, by delegating or automating your processes you’re able hand off the 80% which takes time from your day and focus on the smaller, more specialized chunk of work that only you can do.

It’s important when working remotely to be as productive and efficient as you can because you’re at an inherent disadvantage and more prone to distraction.

By making sure that your data entry and busywork is taken care of by others or automation, you can concentrate on pure output.

A big time-saver is integrating your apps. Without integrations, you’re going to spend a ridiculous amount of time transferring data between your apps.

Check out TeamViewer’s list of integrations which include JIRA and Outlook to get an idea of what you can do when your apps speak to each other.

Even though I’m comfortable with formatting, editing and data entry, my main skill is writing. I used to spend 50% of my time on non-writing tasks, which killed my output, forced me to rush deadlines and write substandard articles.

Now, I’ve realized there are people on my team that are much better at non-writing tasks than I am, and they help me by taking work off my hands and leaving me with more time to do what I was hired for.

Go out of your way to interact with your team

Challenge of BYOD is forming new habits

Unlike in an office, you’re not going to bump into your coworkers in the hallway and decide to go out for a drink.

I’ve learned that you have to work harder at relationships when you’re remote, not only because it’s good to get on with your colleagues, but because communication is smooth when everyone feels comfortable.

I’ve learned to make the effort, say good morning over chat and be friendly, even when it would be easier to immerse myself in work all day and speak to no one.

Being on opposite sides of the world, it’s unlikely anyone’s going to go out for lunch with each other any time soon, so what we do is schedule time outside of work hours to play Hearthstone.

Hearthstone is an interactive card game that’s easy to pick up, and we work with a system that randomly matches us together so we eventually interact and have fun with everyone on the team!

Something Stella Garber said over on the Trello blog has really resonated with me in this year of working remotely:

“Just because employees are “remote” doesn’t mean they’re meant to feel like they’re on a deserted island.”

And it’s true. I don’t feel like I’m in a desolate, remote landscape. I feel amazing for getting work wherever I want, and for communicating with such great people every day.

What are the lessons you’ve learned when working remotely? Share your ideas in the comments section below!

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