5 Challenges of Working Remotely (and How to Conquer Them)
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5 Challenges of Working Remotely (and How to Conquer Them)

Elise Pagnini Elise Pagnini Last Updated:
Woman wearing sunglasses

When you spend your days at home in a virtual office, it can seem that the biggest hurdle remote employees face is finding the motivation to put on real pants.

While the struggle is real (Lululemon for life), there are a few more pressing troubles I’ve come across since I joined Toggl last year – and they don’t involve yoga wear.

Here are 5 challenges you can expect to face when working from home, plus a few tips on showing them who’s boss.

1. Never stop communicating

no waste time talking

When you spend 100% of your time talking to people on the other side of a computer screen, it’s easy for things to get lost in translation. Facial cues, body language and tone aren’t there to help you read between the lines when speaking with customers, superiors or colleagues, so you need to pay extra attention to what you say and how you say (or e-mail) it.

Whenever in doubt, over-communicate and if you aren’t already, take advantage of group chat apps, such as Slack. They’ll help keep your inbox clutter free and give you a quick way to update your team on your projects as well as ask questions when you need help.

2. Build and nurture relationships

cat loves dog

Working in a traditional office, there are plenty of opportunities to get to know your coworkers. From team-building lunches, to coffee breaks and after work drinks – it won’t take long to rack up personal tidbits about one another and learn how to collaborate together with ease.

From home? It’s a bit more complicated, since you can’t ask your office roomie about the picture on their desk if you don’t see it (or share a desk with anyone but your goldfish).

Take a few minutes every day to ask the real people behind the avatars about their weekend, share a funny article, or chat anything non-work related. While it may seem counterintuitive to veer off topic, connecting on a personal level will make you work better and ultimately, help you become a part of the team – even if you’re thousands of miles away.

3. Mind the time difference

mind time difference chandler

Scheduling meetings can seem about as effective as herding cats in even the most well run office. Throw a ten hour time difference in the mix, and it can feel a little bit like you’ve been blindfolded on top of it.

The solution?  Since you can’t just get up and walk over to your neighbor to ask a question, or hunt down your boss in the conference room, you need to get a little more creative and a LOT more organized. Skype whenever you can and pay attention to the daily schedule of core teams. Maximize any overlapping time by sending over questions and checking e-mails as first thing, so you don’t have to wait a whole day for a response – and so neither would your coworkers.

4. Embrace the company culture

entertainment 720 yo

A strong company culture is one of the biggest assets a business can have. It creates a bond between employees, forges a common goal and makes teamwork a lot more enjoyable. So, how do you drink the Kool-Aid when you’re flying solo?

The first step is getting some face time. When I found out I was being offered the job at Toggl, I had a bit of luck since one of our founders was actually going to be in town and invited me to get lunch. Toggl is also a big supporter of bringing remote team members to the office to see where the magic (and nerf gun fights) happens.

While not all companies have the inclination or budget to do the same –it never hurts to ask for some in person training. And if they offer to have you to come to corporate, always say yes. A few days (or weeks) of one-on-one interaction can go a long way in getting you up to speed and on board. Plus, it’s a lot easier to embrace the company culture when you’ve experienced it firsthand.

5. Learn to work in a melting pot

is difference ok gif

Working for an Estonian company that has quite the international crew (we’ve got people in Brazil, Spain, Scotland and Belarus, to name a few), it took some time – and a map – to get my bearings. Pop-culture references, abbreviations and other “common” practices aren’t really that common when you’re dealing with such a diverse group of people. Be prepared to ask a lot of questions, take cues from others, and keep an open mind. While there are plenty of similarities (David Hasselhoff’s musical talents know no bounds), you’ll have moments where the differences can cause misunderstandings and other hiccups.

But as long as you approach each one as a learning opportunity and remain open to feedback, you’ll be just fine. 

Elise is a proud member of our growing remote community. If you feel like Toggl might be a cool place to work, check out our job tests page for current openings. Or have a look at this awesome recruiting video we made.

You can always help us spread the remote way of life and share this post on Twitter.

Elise Pagnini

Elise lives in sunny San Diego with two giant cats who weigh ten kilos each. Elise also lives with her boyfriend, though she did not provide his weight. She loves reading, cooking, hiking, and going to the beach. She is a certified emergency medical technician, which often comes in handy at the Toggl Christmas party.

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