4 Lessons About Working Remotely I Learned the Hard Way (So You Don’t Have To)

Susana Cigano

If the title piqued your interest, chances are you’re either looking to become a remote worker, or you’ve already embraced this lifestyle.

Perhaps you’ve been dreaming about working from the couch while wearing your favorite PJs. Maybe you’re already halfway done planning a round-the-world trip. Whatever your plans may be, there are important considerations to take into account when switching to a remote work lifestyle.

When I joined Loom last year, the team was taking their first steps to become a remote friendly company, so I’ve been fortunate enough to be part of their learning curve.

While the majority of the Loom team still works in the office in San Francisco, there are now a few of us located in different places around the world. In fact, as I’m based in Amsterdam, there are about 5500 miles and a 9 hour time difference between me and my teammates in California.

Getting together for after work drinks is a challenge, to say the least.

Loom retreat in Mexico group photo
But not impossible! Here we are at our first ever company-wide retreat in Mexico.

For the last 7 years, I’ve had a range of experiences, from working with a completely distributed team to going to an office every day. In the process I have learned what works best for me. I’d love to share some of these learnings with you.

I also didn’t want to base this post purely on my own experience, so I reached out to online communities such as Support Driven and Remotive, and spoke with other remote workers to identify challenges they face on a daily basis.

I hope this post helps you tackle some of the everyday headaches that inevitably come with working remotely.‍

Be intentional about communicating. And over-communicating.

We’ve all heard the saying before – communication is key. This is true of any relationship, including (of course) the relationship you have with your co-workers. When you’re all in the same place, attending the same meetings, and having the same water cooler conversations, it’s easier for everyone to be on the same page.

Vinay slack message asking for the team to over-communicate
Our technical co-founder Vinay asking the team to over-communicate during a project.

It might sound excessive, but over-communication can actually be the key to making sure everyone knows exactly what is happening in your company. With something as important as work communications, it’s better to be safe than sorry. This doesn’t mean you’ll be sending your every thought to your coworkers in a Slack message. It simply means that you will have to double down on what’s essential for your team to know.

What has worked very well for us at Loom is agreeing on what’s important for us as a team. And since most of our core values are centered around transparency, curiosity, and empathy, it’s no wonder our small team likes to over-communicate.

Loom team meeting
Every Monday the entire Loom team aligns on the week’s priorities.

Here’s a few things my team and I do to make sure everyone is on the same page:

  • #no-mo-fomo Slack channel: document all important team updates in Slack so no information is lost.

  • Hold quarterly meetings where all company metrics are discussed, including how much money is left in the bank.

  • Our Customer Success Manager and I record daily updates with our progress on different projects so that when I finish working, Ian knows where he needs to pick up from and vice-versa.

Of course, the expectation to over-communicate goes both ways. Both you and your team need to make sure you’re keeping each other in the loop. Consider documenting your most important information in a workplace wiki.

If you’re not 100% sure someone read your email, send it again! If you’re nervous about annoying your colleagues, get rid of that worry. Your intentions are good and, in the end, your team will thank you for not missing out on important updates.

Better yet, set up a meeting or record a video for them. It will liven up your work communication and build team spirit much easier than text-based emails that people are scanning over anyway.

Working from home might cost you a promotion.

It’s a common feeling amongst remote workers that it’s harder to prove yourself to your manager when working remotely. It’s not just in your mind, either – in a study of 250 remote workers, the New York Times found that remote workers were 13% more productive than their in-office counterparts, yet half as likely to be promoted.

With in-office jobs, you have the luxury (and sometimes curse 😉) of having your manager close to you as you work. It can feel easier to communicate updates or schedule impromptu meetings to show your team your progress.

When you work remotely, you need to be more intentional about your communication. I just wrote a whole section on over-communicating and I stand by that principle. There’s a lot of blind trust required when working remotely. It’s not always easy to check on someone’s progress, how much work they’re actually doing, how long they’re working for, or what they’re up to.

You get my point. Trust is essential for any office-remote relationship to work. Humans are visual creatures, so why not take advantage of our brain’s predisposition for visualising information?‍

Here’s how we share updates on our progress at Loom:

  • Team wiki hosted by Notion:

    We strongly value transparency and we do our best to document everyone’s tasks, workload, and roadblocks in our team knowledge base so that progress can be checked at any time.

  • Path reviews:

    Each Loom teammate has an individual Path for their career journey. Every month, manager and direct report sit together and reflect on the work done to achieve the goals laid out in the Path and plan future milestones.

  • Video updates:

    For each project we participate in, we record daily video updates on our progress to ensure everyone can quickly be brought up to speed if needed.

Spending time documenting your work might sound like a hefty task but consider it for a second. Having a detailed description of your hard work at hand is incredibly valuable when you’re due to have a performance review with your manager. You’ll thank yourself later.

‍Be proactive in ending your work day.

Disconnecting at the end of the day seems to be a universal concern for people working remotely, especially when your team is spread across multiple time zones.

I am definitely guilty of this myself.

Slack messages signing out of work for the night

When you’re going to an office, you know your day starts when you arrive at your desk and ends when you go home. This physical delimitation of your day works as a helpful mental switch between your work and personal life. With remote work, your wires can easily get crossed. Your personal space might also be your workplace, and there’s no physical difference between the two.

Everyone works differently, but the most important tip I can give you is to create an exclusive work space. Whether that means going to a co-working space, or just having a specific desk where you do your work, make sure you take steps to keep your work life separated from your personal life.

Personally, I don’t have the space for a home office and I don’t go to co-working locations very often, as I find I’m most productive at home. What ended up working best for me was getting a dedicated desk that I don’t use for anything else. When I’m sitting (or standing) at my desk, I’m at work.

Home workspace
Having a dedicated space to work is very helpful to create balance between personal and professional time.

Some other things I’ve been experimenting with:

  • Blocking my calendar with ‘personal time’ at the end of my day prevents impromptu meetings from being scheduled and ‘taking over’ my evenings.

  • Blocking my calendar also works great for meal times for those of us who tend to forget to eat.

  • Trying to have some personal time in the morning if I know I will need to work late that day.

  • Not having Slack notifications enabled on my phone.

  • Getting a dog. I’m only half joking. I WILL get one. 🐶‍

Actively seek ways to involve yourself in your company’s culture.

Another challenge raised by the people I spoke to is not feeling entirely connected or involved in their company’s culture. As remote workers, we might feel a bit lost and isolated when it comes to building rapport with our teammates.

Comment saying that it is difficult to miss out on the regular in-person socialization

Unfortunately, there isn’t a clear solution here. As great as working remotely might be, there’s no way to simulate office life with your colleagues and that means there might be some things you’re missing out on. You’re not there to celebrate special moments, have lunch together, or hang out with the office pups.

The key here is to make sure you have fun together, even if you’re only connecting virtually. Just because you’re not in the same place doesn’t mean you can’t enjoy getting to know your colleagues.

If you are having a hard time connecting with your team on a personal level, here are some of the things we do at Loom to engage with our remote teammates:

  • ‘Funky Monkey’ meetings every Monday with the entire team. We spend one hour reflecting and celebrating our team. From giving each other props to talking about areas of improvement, this is our sacred time to get the team together and be a little weird.

  • VR 1:1 meetings – our awesome People Ops Lead, Rachel, purchased VR sets and now remote teammates can ‘hang out’ with the in-office people in a virtual room. We’ve had a few of these calls and it was literally out of this world.

  • Making sure we celebrate special moments together. Yes, that sometimes means our San Francisco team might have to do a cheers with Mimosas on a Thursday at 10am while I have a glass of wine at 7pm in Europe, but it’s the thought that counts, right?

Celebrating with a glass of wine
Celebrating Loom’s 2 year anniversary with the team.

Working remotely is not for the faint of heart.

Once you decide to cross over to the remote side, there’s no turning back. For me, the flexibility of getting to choose where I work and how I organize my day vastly outweighs the challenges I face.

The key to success is to work hard to find alternative ways to accomplish what might be easily accessible to your office counterparts. Most of the frustration that results from working remotely can easily be traced to mismatched expectations.

As long as you’re mindful of the things you might be missing out on, like the luxury of sharing a physical space, you can more than make up for it and lead a healthy remote working life.

And, in the meantime, don’t forget to over-communicate! 😊

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Written by Susana Cigano

Manager, Support @ Loom

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