Illustration by Bronwyn Gruet
Illustration by Bronwyn Gruet

Working Remotely: Tips from 100+ Remote Workers & Leaders

It’s a unique time in the history of remote work. At Help Scout, we’re big proponents of it — with 100+ people working in more than 80 cities across the globe, it’s been part of our company DNA for nearly a decade.

But none of us could have predicted the effects of COVID-19, which thrust countless companies and employees into a “work from home” environment virtually overnight, feeling ill-prepared to make it work.

While we aren’t qualified to speak on the human tragedy playing out, we are in a position to offer a little guidance to folks who never opted-in to this way of working but are forced to do it anyway.

This resource is a compilation of all our learnings on working remotely through the years.

First, a caveat

Working from home is very different from how “remote first” companies operate, at least by our definition. Let’s explore the difference:

  • Remote first is a way of working that’s infused into a company’s culture and communication infrastructure. Everyone plays by the same rules; it’s part of the company’s identity.
  • Work from home is when you have the option to do your job outside of a company office, yet the company remains primarily optimized for co-location.

When people criticize working from home, it’s important to understand the distinction between these two terms. In our view, the difference is night and day.

If you are working from home by necessity due to COVID-19 or something else, you should expect it to be sub-optimal. It’s quite different from working in a company that’s been instrumented from the ground up to do remote work well — global pandemic or not.

However, all is not lost! This resource exists to help people in both camps. Although we’ve built our company in a remote first way, there are several things you and your company can do now to make the culture more fun, more engaging, and more productive so that business and some sense of normalcy can be achieved. Let’s dig in!

Remote team collaboration

Between remote and co-located work, there’s no right and wrong way. Thriving cultures exist on both sides of the spectrum. The key to success is understanding and proactively addressing the various tradeoffs.

For instance, offices are notorious for interruptions and distractions, whereas working remotely is more attuned to deep, distraction-free work. But that’s only one side of the tradeoff.

On the other side of it is the water cooler. Building relationships and getting to know folks on a deeper, more personal level happens naturally in an office. You really have to work at it if you are remote, which often means setting aside dedicated time to get to know your teammates and build relationships.

Recommended Reading

6 Tips to Keeping Your Remote Team Connected
6 Tips to Keeping Your Remote Team Connected
What Remote Companies Can Teach About Asynchronous Communication
What Remote Companies Can Teach About Asynchronous Communication
Why Water Cooler Talk Matters More Than You Think
Why Water Cooler Talk Matters More Than You Think
How We Use Video to Build Remote Culture
How We Use Video to Build Remote Culture
How to Handle Conflict on Remote Teams
How to Handle Conflict on Remote Teams

How to be productive when working from home

How do you know people are working?

I get this question a lot from folks who aren’t familiar with remote work. If you measure productivity by “butts in seats” time, is that the right measure? Most people would agree that showing up for work doesn’t mean the person does a great job.

What we should be asking is, “How do you know people aren’t working too much?”

Seasoned remote folks will tell you that working in your pajamas, not leaving the house, and collaborating with teammates asynchronously will make you susceptible to burnout. Most of us have experienced it.

As a manager, you should keep an eye on this, along with symptoms of imposter syndrome or employees not feeling that their contributions are enough. These are complex challenges that are more difficult to diagnose when you aren’t in the same physical location.

Recommended Reading

Six Ways Remote Teams Can Crush Their To-Do Lists
Six Ways Remote Teams Can Crush Their To-Do Lists
The Digital Nomad’s Toolkit for Staying Productive
The Digital Nomad’s Toolkit for Staying Productive
Lessons Learned from 6 Years of Working in My Pajamas
Lessons Learned from 6 Years of Working in My Pajamas
9 Tips for Working While You Travel
9 Tips for Working While You Travel

Leading a remote team

Leading people remotely is more difficult. Not what you were hoping to hear? I’m sorry to disappoint, but I’ve been doing this for fifteen years and that’s been my experience.

Yet I’m still passionate about remote work and leadership. There’s no way I’d go back to a co-located setup. There are two very important and worthwhile reasons:

  1. Access to talent – Working with people who are at the top of their field, who challenge me, and who bring diverse experiences and perspectives to the table is one of the greatest joys in my life.

  2. Talent can thrive – While being a leader/manager of a remote team is more challenging, it’s easier for creative folks to do their best work. It’s a combination of focus, flexibility, and setting that facilitates higher-quality output. Since I ultimately do what I do to support creative people’s work, I find this to be a trade-off that leans in favor of remote work.

If you believe success is about the people, it would be difficult to say that limiting your talent pool to a 20-mile radius of an office is the best way to be successful.

Recommended Reading

How Our Remote Team Stays Aligned With Town Hall Meetings
How Our Remote Team Stays Aligned With Town Hall Meetings
Organizing Teams With Players and Coaches
Organizing Teams With Players and Coaches
6 Tips for How to Collaborate on Remote Design Teams
6 Tips for How to Collaborate on Remote Design Teams
The 6 Best Remote Collaboration Tools for Customer Service Teams
The 6 Best Remote Collaboration Tools for Customer Service Teams

Hiring and onboarding remote employees

If you ever have to hire, onboard, or let go of employees in a remote way, it’s a whole different thing. We’ve seen all sides of it over the years and documented what we learned along the way in the following articles:

Recommended Reading

Help Scout’s Step-By-Step Remote Hiring Process
Help Scout’s Step-By-Step Remote Hiring Process
A Detailed Guide to Remote Employee Onboarding [+Checklist]
A Detailed Guide to Remote Employee Onboarding [+Checklist]
10 Tips for Knocking Your Virtual Interview Out of the Park
10 Tips for Knocking Your Virtual Interview Out of the Park

Curious about going remote first?

If you are trying to make your way through an unexpected work-from-home period, our hope is that the resources above have offered some ideas and guidance. But if you are considering going all-in — either as a company or as an employee — we’d love to help you figure it out.

Also, we’re hiring. 😃

Remote work tips from the Help Scout team

We asked employees at Help Scout to offer their best tip for someone working from home, in two sentences or less. Here’s what they said:

Megan Chinburg

A pomodoro timer helps keep you focused and reminds you to take breaks. Also be sure to set Slack/email notification sleep schedules so you can keep the work-life separation you need.

– Megan Chinburg

Kristi Thompson

Working from home with a partner is great for preventing loneliness, but it does present some challenges. You can avoid frustrating distractions by communicating with each other about what you need and setting a few boundaries you both agree on.

For example, my husband and I work right next to each other at the same big desk, but we raise a hand before talking. It might sound ridiculous, but there's nothing worse than being interrupted in the middle of deep work. If it's not time sensitive, we'll often send each other a message online instead.

– Kristi Thompson

Gilberto Valverde

Headphones with a microphone usually work better picking up your voice during a video call than the laptop’s built-in mics.

– Gilberto Valverde

Virginia Ulrich

More often than not, your coworkers cannot see you react — you have time, space, and privacy(!) to put your best self forward. Make that a superpower. Take the time to process, calm down (if needed), and then reply with the impact you might have fully in mind.

– Virginia Ulrich

Buzz Usborne

End your day by sharing a one- or two-minute video with your team showing what you’ve been working on (Loom is great for this). It’s quick, requires no preparation, and connects your team to the person behind the work.

– Buzz Usborne

Elyse Roach

Create a workspace that you use during working hours only. Doing that helped me keep a hard line between work and home, which was incredibly helpful during the remote transition!

– Elyse Roach

Tessa Nordgren

Set aside fixed time for breaks; set reminders on your phone if you have to. You need to pace your day according to your own needs, and intentionally doing so will make you more productive.

– Tessa Nordgren

Scott Alexander-Brown

Get decent noise-cancelling headphones. Then, regardless of your remote environment, you can have your personal bubble of productivity.

– Scott Alexander-Brown

Alison Groves

There is a tendency to work more while working remotely. Take proactive steps to avoid burnout.

– Alison Groves

Borys Zibrov

There’s a ton of stuff going on online that is not work and eats up real time in the end. Your brain is wired to procrastinate, so make sure you’re aware of that and consciously choose where to direct your time (it sounds easier than it is, I know!).

– Borys Zibrov

Chris Kiser

It’s not something I do every day, but trying out a time diary in my early months working remotely was really helpful with zooming out and understanding where I was spending my time and energy. It helps identify the best way to organize my day for both work and personal life.

– Chris Kiser

Casey Lockwood

Remote work requires a certain comfort level with async work. As a result, you’re forced to solve a lot of your own problems. Know where to find things and be comfortable digging into your organization’s resource network to self-serve.

– Casey Lockwood

Julie Cousins

Find a ritual that separates work time from home time (I use walking the dog). Get dressed for the day as if you were going out.

– Julie Cousins

Katie Harlow

Use Krisp noise cancelling app to reduce background noise on calls or videos, especially if you find yourself suddenly working remotely with others in a small space.

– Katie Harlow

Juan Pereira

When I started working remotely I had imposter syndrome, and tools like RescueTime helped me understand how many hours I was putting into work and it also helped me improve my productivity.

– Juan Pereira

Corey Nilan

Get dressed, even if it’s not to the level of the type of outfit you’d wear to the office! Changing out of your pajamas helps you wake up and switch to work mode.

– Corey Nilan

Paola Maciel

Make time to be away from screens/technology during the day. Personally, I prepare my lunch the night before so that most of my lunch break can be spent outside (without my phone).

I also find it helpful to add some variety to my work space. Throughout the day I sit at my desk, stand at my desk, sit on the floor, use the cat tower/kitchen counter/stacked books on the balcony as a standing desk ... not everyone's cup of tea, but I love and cherish changing it up at different points of the day.

– Paola Maciel

Nickolas Kenyeres

Having a dedicated room for my office, and not using it outside of working hours, is an effective way for me to create boundaries between work and home.

If you're in a situation with other people home during the workday, sharing schedules or giving someone a heads-up that you're stepping into a meeting is a great way to avoid disruptions.

– Nickolas Kenyeres

Morgan Smith-Lenyard

Be honest with everyone you work with. If you don't understand something, if you need more time, if you're feeling overwhelmed, if something's bothering you — don't be afraid to tell the truth.

In a co-located work space, there is the luxury of body language, tone, and even someone's appearance (e.g. Amy from Accounting is always dressed to the nines and the past week she has come in disheveled). When you're communicating mostly async, things can be missed if you aren't up-front.

– Morgan Smith-Lenyard

Becca Van Nederynen

Put on a bra (if applicable).

Don't give up! Keep experimenting with different routines until you find one that feels good.

Join @workingrem's weekly Wednesday #RemoteChat on Twitter to connect with other remote workers.

– Becca Van Nederynen

Vesna Djokich Leonard

Over communicate. All. The. Time.

They say that to parents teaching kids how to speak. When doing their daily tasks, parents should speak out loud and tell the kid what they're doing: "Mommy's washing the dishes now," "We're going to the park to walk the dog," etc. Do that.

Keep communication continuous, wide open, and fully transparent.

– Vesna Djokich Leonard

Dan Svizeny

If you have pets at home, make sure they are ready to work around your schedule. It's always a good idea to keep some toys and treats handy in the event you find yourself in back-to-back meetings.

– Dan Svizeny

Tim Thyne

Embrace remote and bring people into your world — let them meet your kids/dogs/cats/birds/etc. They're not distractions; they're part of your life, and one of the best parts of remote work is the integration of both during the work day.

– Tim Thyne

Anthony Gass

If you don't have your own office or dedicated room to work from, have your desk face away from everything else going on in the home. Combined with headphones (even if you just listen to instrumentals or white noise), it will help you stay focused and productive.

– Anthony Gass

Abigail Phillips

Actually shower. Do it.

– Abigail Phillips

Additional working from home articles

Ready to learn more? Here are a few resources we love from other remote teams.

Nick Francis
Nick Francis

Nick is co-founder and CEO of Help Scout, where he is on a mission to make every customer service interaction a more human one. He lives and breathes product design, customer experience, and building a thoughtful, thriving company.

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