People People

Adrian Coffey
Upside Team Blog
Published in
6 min readOct 8, 2020

In June of 2020, Upside Business Travel made the decision to become a fully remote company for the foreseeable future. I walked around our empty office space this summer as we prepared to move out noticing bottles of water and winter coats draped over desk chairs. We’d all anticipated we’d be back soon when we left that day in March. We’d want those winter coats to be waiting. Now we know we won’t be coming back at all and we’re faced with the challenge of adapting and redesigning our culture for a long haul remote world. We’re not the only company grappling with this new challenge. Twitter, Shopify, Facebook and many other tech giants announced plans to abandon the concept of a central office culture and rethink and redesign the everyday lives of their workforces. 2020 has left an indelible mark on the landscape of work as we know it and that landscape and idea of office culture has been permanently changed.

The “solutions” will look different for every company and even for every person in every company. What works for me might not work for Mic. And what works for Mic might not work for Erica. As people who spend our days thinking about company culture, we must now start at the beginning and take into account the differing needs across our companies. Despite being a company that eschews the traditional concept of structure, we’ve now come to realize that we did in fact have structure baked in everywhere. We might not have ever said it or written it, but the mere fact of our physical proximity to one another created social cues and thus structures that shaped the way we worked and interacted with one another. For instance: you would never watch your entire office walk to the kitchen for a company meeting and decide you’d stay at your desk and eat lunch — you’d feel too uncomfortable. But now, it’s easy to turn your camera off or just bail all together — maybe no one will even notice. And so we, along with many other companies, need to completely rethink how we operate. We’re committed to the idea that this is a design challenge — we need to start with how people are feeling, what’s keeping them up at night, what’s causing them heartburn during the workday — and build out from the feeling.

As I began to grapple with these questions and challenges, I started by thinking through my own personal day to day qualms with my new remote life. I am a real extrovert — I love to feel connected and feed off of the energy of my loved ones (and yes, at Upside, my colleagues are loved ones!). So what happens for someone like me when the world is suddenly forced to remain decidedly disconnected for months on end?

I am really struggling with our new all remote, all the time world. I don’t like working from home. There, I said it. It’s a necessity right now and I am very grateful that Upside recognizes that and is committed to the health of not only my colleagues and me but of our families as well. Not all of my friends are so lucky. But, it’s still hard for a people person to be “alone” all day. As someone who leads our talent acquisition function, my day is packed to the brim with zoom calls, interviews and slack messages galore. But, some days there’s something missing.

My manager recently said “I don’t want to watch someone make a brownie on my screen, I want to chew a real brownie” and her point really hit home. I didn’t want to just see her on my screen anymore or look at framed pictures of my colleagues. I wanted to look (six feet!) across a table and have a real brainstorming session. As “people” people we both thrive on human connection and get a lot of energy and ideas just by talking things through with one another. And some days, that just wasn’t translating over Zoom. We had a lot of really big things on our plates to tackle and we realized we were really feeling disconnected from one another — a real rarity (and thus a real drag) for us.

We’ve always done some of our best “thinking” work over pancakes or guacamole, so we hatched a plan. We shared our quarantine standards with one another, agreed to stay outside and hopped in our cars in search of guacamole and camaraderie. Now, that our company has gone fully remote, we aren’t in the same state, so we decided to pick a halfway point (hello, Wilmington, Delaware!) and meet for an al fresco working lunch — -guacamole included.

We spent a large portion of our time chatting idly while we both typed away on our computers — something that I miss terribly about being physically separated from my colleagues and something I’ve come to learn is important to my own productivity and workplace happiness — and an equally large portion of time developing a new initiative we’d been batting around and maybe even struggling with for weeks. Unsurprisingly, once we were together in person again, it all clicked and came together beautifully and that afternoon in Delaware.

As I drove down 95 that evening through the slog of Baltimore traffic, I felt better and lighter than I had for ages. I felt productive, I felt connected, I felt the old Upside feeling again and it reminded me that we as humans, at our core, need to be connected to what matters to us. Meeting in person is surely not for everyone yet — -or ever, and there are many other ways to remain connected and solid even while apart — to connect to what matters to you. Our team has instituted bi-weekly happy hours, exercise classes, virtual coffee dates, cookie decorating events, morning all company check in’s and while all these things have been major bright spots during our time apart (and will continue to be) — we know there is more work to be done.

As our team plans to stay fully remote for the foreseeable future, energized by our own meetup’s, we’re working hard to design a new experience for our team that will make remote life a little bit easier for many different types of people and in many different life scenarios. We have long held Upside’s culture as one of our biggest sources of pride and we’re committed to that for the long haul. We’re all redesigning the future of work one zoom at a time and while it’s easy to simply try to take the “what we had” to the magic of the internet, it’s imperative for companies to take a deep look at their culture and how it may or may not work in this new world.

So while it may seem daunting, we’ll order an extra large batch of guacamole and get to work designing the Upside of the future. We can’t wait. See you soon Wilmington.

What are some ways your company has stayed connected in a remote world?

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