The Highs and Lows of Remote Work

How to thrive as a small (and mighty) global team 💪

Groove is a remote-first team distributed across five time-zones 🌍 After a little over a year of being fully remote, we sat down to discuss our favorite parts of working remotely and the challenges we’re still working through. Read on for a real conversation about the good and the bad of remote work, from our point of view 🕺🏼.

What are the best parts about working from home?

Tova Safra, Co-Founder and Chief Design Officer:

Being an introvert is, I think, going to color my answer here 😊

At this particular point in my life, I like spending some of my day alone, and I also have kids so my alone-time is very limited; I really value it. Whenever I worked at in-person workplaces and they wanted to do social events and things that were after the regular workday, I always thought, “Well this is okay, but I’d rather be home with my family right now.”

I’m also an artist, which I think requires some amount of introspection and alone time on a regular basis. So I prefer working at home, where people aren’t around you 100% of the time, like they might be in an office. Too much alone-time during the day can feel numbing and demotivating, which is a problem I solve by doing Grooves.

Taylor Harrington, Head of Community:

I feel an insane level of connection on a daily basis inside the Groove community and team. I could have never imagined this two years ago. We’ve intentionally crafted a remote-first team culture, with synchronous and asynchronous creative brainstorms using Figma and Notion, regularly scheduled meetings like ‘sprint planning’ where we align on our goals for the week, and short weekly check-ins to share strategic updates.

The amount of daily connection I get is actually so high between our team connecting and Grooving with community members, that it’s extremely important for me to continue working on how I create boundaries for working hours and manage my time spent alone vs. with others virtually.

Another major perk of working remotely is that I was able to easily spend 15 days recently working remotely (and taking time off too!) from a sunny and warm location 🏝

Josh Greene, CEO and Co-Founder:

I think what’s most powerful for me in remote work is the freedom and flexibility to see work as part of my life that I can that I can move more fluidly through my week. It means that work can be less important at some point and more important than others times. This means I can regulate my day in healthy ways that don’t have to be in one specific place.

The hardest thing that I’ve learned over the last couple of years of remote working is there is a flip-side to flexibility. How do I feel like how do I have structure? How do I not let work creep into my evenings or to my to my sleep? Finding habits to protect boundaries around work is the key to having a remote life that actually works for me.

We made Groove remote because that’s how Sruli (co-founder) and I really want to work. But, remote work is only possible if if you have structure, community, and connection around your work. We felt that to build a product that was supporting people to do that in their lives we had to be able to do it for ourselves.

What are the challenges in working from home?

Tova Safra, Co-Founder and Chief Design Officer:

I think that the biggest challenge with being a fully distributed team is being able to build trust and rapport, as well as being able to tell if someone is on the same page as you emotionally about a certain issue or decision that needs to be made.

We’ve made some mistakes and learned a lot. Decision making, especially as it relates to design and creatives, is not easy to do consistently, and at high quality, when a team is remote-first. I had so many thoughts about it that I started writing down our learnings as we went along, and I wrote them up in a dispatch.

Taylor Harrington, Head of Community:

When I was looking for a new job in 2021, I was so scared to work remotely full time, but the world was still so remote-focused, and I didn’t want it to hold me back from interviewing somewhere. And, I thought if the company was remote to begin with I could help design that remote culture with care.

When I first read about the problem Groove was solving, I thought, “This is what I’ve been wanting for a while now.” Back in college, I had dreamed of finding a way to connect with our entrepreneurial-minded folks from around the world.

While I was extremely excited about the offer to join the Groove team, I was so nervous about joining a distributed team where mostly everyone was working 7 hours ahead of me in Israel. At the time, Groove was a small team of a couple of full-time co-founders and a few freelancers. I was very transparent about my concern with Josh and we talked through what we might implement in order for me to feel like I could be successful and happy in a remote role. Regularly scheduled check-ins, async audio notes (which I love as a form of communication!), Grooving together, and the opportunity to work from a coworking space were some of the upfront agreements we had. And, Josh, reminded me, by Grooving I might be able to get some of that connection I’ve been craving.

My biggest challenge as a remote community leader is actually finding more time to spend alone and turning things off at the end of the workday. The coworking space I go to helps enforce those boundaries. It’s a quick 12-minute walk from me and the three community leaders there, greet me with a loud, “TAAAAYLOOOOOR!” every time I walk in. I’m a regular somewhere, and that feels really special.

I’m really looking forward to the day we do get to meet up as a team in person, but until then, I’m extremely grateful to be on a team that is so open to trying new tools to connect and collaborate virtually and think intentionally about how we can design our workdays and culture.

Josh Greene, CEO and Co-Founder:

I think the first challenge of remote work is that you have to put in more effort to find forms of communication that work for everyone. Whether that’s how you use different software platforms to share things that are asynchronously written, or shared with voice notes — there’s a lot of work to just find ways to connect. It also means that you have to take the time to debrief and talk about what’s working and what’s not. You have to be more sensitive than you might in an office because the norms aren’t as clear.

Groove creates a much more connected experience of work, a structure, and ability to package and share what you’re working on, into concise ways. Because the Groove team Grooves together, I think that helps create internal visibility and awareness about what we’re all working on. That’s helpful for our small team to know about what’s going on with each other– like peers know what they’re doing across teams, etc. Remote work would be a lot harder if we didn’t have Groove.

Looking for more Groovy content? Check these out:

1. Can Parents Make Time for Deep Work?
2. The Future of Work (as we see it)
3. Start getting sh*t done the fun way at ➡️ Groove.ooo