Sift Voices
November 15, 2022

Work at that Remote Work Culture

A few weeks ago I attended Adobe Max. It was the refreshing push that I needed as a creative. There were so many takeaways from all the talks, but one has stuck with me the most.

Patrick Holly’s session on remote work, aptly titled “This Is How We Work Now: Establishing a Remote Work Culture,” has been on repeat in my head for the last few weeks. Not only because he’s a seasoned designer and leader (he’s currently an Executive Creative Director at Upwork and comes from the likes of Harley Davidson, agencies like AKQA and R/GA, and not to mention is Stephen Curry’s creative director), but also due to his passion and advocacy for remote work.

It was the session I was looking forward to the most. Anyone working now in the prolonged Covid-pandemic has been searching for that next edge. With nearly 1 in 4 HR leaders expecting over 90% of their workforce to be remote into 2023, it’s no secret that companies are searching for the best solution to get and retain top talent. Even here at Sift, over 80% of my team members work remotely or live outside of Michigan. We have the office space if we need to huddle up in person or for whole company events, but we mostly work virtually. I wanted to bring back something to my team that could keep us engaged while being so far apart.

Connect as people

Sitting in my seat and waiting for the session to begin, Patrick starts to ask the room questions, although a bit awkwardly. “How was your weekend? Did you do something fun?”

Something to break the metaphorical ice and get the audience warmed up for a dialogue, rather than a one-sided talk. All it took was one person to answer candidly, “It was fine, nice actually, thanks for asking,” for others to start joining in.

It was the first concept of many: begin every meeting with something not work-related. Patrick brought this routine to Upwork’s Monday Sync; for the first 15 minutes people give each other praise and recognition. He suggests starting any meeting with something completely irrelevant, like a snack review from a local grocery store or posting a picture of the inside of the fridge while folks guess who it belongs to. Anything simple and quick that allows you to connect with your colleagues on a deeper level.

We already do this at Sift. The whole company meets every Monday to go over the previous week’s work and the current week’s intentions. We always kick off with 15 minutes of Best & Thanks with three prompts: let us know a personal best from the weekend, give a business thanks to someone in the company for helping out with a task, and a completely random question that allows our team members to share a little bit of themselves they might not otherwise do. Rather than everyone silently waiting for it to start, we can begin on a collective note of positivity, and the feel good “thanks for asking.”

Credit: Patrick Holly's presentation

Work is not daycare

As we all navigate this space, fear of the unknown can soil a remote work culture. Patrick leans into the notion that managers don’t trust their people unless they have "butts in seats." They are so focused on the input rather than the output that it can ruin teams and talent. He describes instances of lack of accountability and connection with team members (both in-house and freelance) when he first took on his current role. A new study by Airspeed finds 75% of executives surveyed believe their employees would give up a lot to work for another company where they’d feel more connected.

But we can build connections virtually and in-person. Patrick’s team meets up at least quarterly, whether it’s the whole team or as leadership, to get in that face-to-face time. Work isn’t talked about at all. They book retreats and outdoor activities to connect with each other offline and out from behind a screen. They find a food truck and eat too many hot dogs while giggling with each other.

Because of this intentional connection, empathy for each other can start to grow and you see a coworker as a person, not just Janet from Accounting. When it comes time to have serious conversations and tough talks with someone, it doesn’t feel like you’re talking to them for the first time. You’ve been building that vulnerability and trust, person-to-person.

At Sift, we were only meeting once a year for this offline bonding. We could conduct a quarterly retro or company bonding exercise, walk across the street to a Detroit Tigers game, and talk with each other over food and drinks afterwards. All the while, switching up who we sat next to, engaging in conversations and laughter about life rather than the project at hand. I’ve learned and felt that deeper connection with fellow Sifters that I don’t get to see outside of our Monday meetings.

We’ve expanded this bonding by instilling a Sift Events Team, a diverse group of Sifters from different departments that come up with fun virtual events to keep us engaged with one another while we figure out our next in-person event. It’s the small things like trivia, a pumpkin carving contest, even a monthly Lunch and Learn hosted by different departments, that bring us together for fun and connection outside of the daily grind.

We're a very creative bunch!

The golden rules

Patrick also iterates how valuable it is to craft values that work for your team. It can be anything that you and your colleagues can utilize as guideposts for operating in the remote setting. He lives by treating your team with kindness, having clear communication set in place, crafting your process into something sustainable, showing humility not only to yourself but to others, and focusing on what drives your colleagues to best help them. Assume the best when it comes to interactions and hold space for vulnerability.

I connect with my team lead on a weekly basis to discuss how the week has been going, talk candidly about personal life and upcoming trips, and get updates on the business. It’s a dialogue, two people having an open conversation about everything. I’ve vented to him about projects that I’ve lost motivation on and we can game plan on how to overcome roadblocks and frustrations to get to a better place. We work as a team because that trust and kindness is there. We’re both remote workers and have built our relationship virtually. I’ll be open and honest here too: it’s a reason why I stick around. I get open communication, accountability, and connection wrapped up in an hour-long weekly talk.

Sweat the process

To wrap up the session with Patrick, he touched upon the most effective and difficult part about remote work: process, process, process. It’s not going to be easy. It’s not going to be fun, either. Find something (and it can be very small to start), and stick to it. Execution is how remote work thrives and continues to grow. Don’t throw in the towel when something isn’t working. Sweat the process and keep tweaking until it clicks. Working remotely is not like working in the office, so don’t treat it the same.

In all, I left the session feeling confident about how we handle remote work at Sift. No, I didn’t learn anything new or edgy to take back to my team, but it’s satisfying to discover that we are already doing the same things as a top team at one of the world’s best freelance marketplaces. If anything, it made me happy to know there isn’t a secret sauce to this culture. Just listen, empathize, and keep iterating your process. You’ll see it click one day, it just takes time – and that one person to break the ice.