Promoting trust and employee engagement with remote teams: An interview with Danielle Wiley, CEO, Sway Group

Successful teams trust each other, but that trust isn’t built overnight. Good leaders use systematic approaches to foster employee engagement and build trust over time, many of which tap into the in-person nature of the office environment. When teams work together and, in many cases, live near each other, creating a space where employees feel a connection with their colleagues can fairly natural. 

But when teams are dispersed or distributed in a remote work setting, many challenges can arise, and the approaches that leaders might have used with their in-office teams need to be adapted to fit the ever-changing work environment. 

Recently, we spoke with Danielle Wiley, CEO of Sway Group, a remote-first company that helps companies grow their brand through digital and influencer marketing. For over ten years, Wiley has led a fully remote team, so she has firsthand experience when it comes to building trust and promoting employee engagement. Here, she shares her insights and expert advice. 

Flexspace (FS): Tell us about the challenges you’ve encountered managing a fully remote team. 

Danielle Wiley (DW): We’ve been remote from day one. It’s both a blessing and a curse. In terms of the pros of a remote team, we can hire the best person for the job regardless of where they live. We also don’t have the massive overhead of office space and everything that entails. Finally, our employees really appreciate our remote and flexible work environment (we also follow a four-day workweek). Most of them are moms and having a job without a commute is a huge benefit. 

The cons of a remote team are all pretty obvious. It can be difficult for team members to truly get to know one another and bond. It’s also sometimes more difficult to solve problems when they arise. For example, if we are tackling a big project, doing so via Zoom takes a lot more time than doing so in a conference room. This also extends to interpersonal conflicts. When I worked at a big agency and two of my employees had a conflict, I’d give them a Starbucks gift card and send them down to the Starbucks in the lobby to sort everything out. That sort of thing is a lot trickier in a remote environment. 

FS: What has surprised you, positive and/or negative, about managing a distributed team?

DW: I don’t know that I realized how much work it is as a leader. I definitely have to make more of an effort to connect with team members who I don’t interact with regularly in my day-to-day duties. In an office environment, you bump into people at the coffee maker, in the hallways, etc. Working remotely, I have to schedule meetings (which ends up terrifying junior employees) or make an extra effort to be active in our non-work Slack channels.

FS: What approaches do you use to ensure your team stays connected when they’re not physically together?

DW: We do all team meetings once per month. At these meetings, we share business information but we also usually include something personal (like making a Powerpoint with childhood photos of everyone and guessing who each one is). We also have anti-oppression training once per quarter that involves the entire team. These trainings often get very personal and deep, which allows us to get to know one another better. We do try to bring people together in person when possible. We do an all-company retreat every year or two and certain teams try to get together 1-2 times/year for planning or to work on big projects.

FS: When it comes to building rapport and trust with new team members, how do you approach that?

DW: The aforementioned “fun” Slack channels are huge when it comes to helping new people feel like part of the team. We have one for book recommendations (I Love Big Books), a Water Cooler channel for random chit-chat, one for meal planning, one for people who love Peloton, and even one for Trader Joe’s recommendations. We don’t bring on new people super often, so it’s not a huge lift for us, but we also do try to let them meet at least one person live if possible (usually based on what department they are in and where they are located geographically).

As you can see, building trust and promoting employee engagement with a dispersed or distributed team is entirely possible. However, it’s imperative that managers take systematic, and in some cases, creative approaches in doing so. For in-person meet-ups, as Wiley engages in with her team when possible, Flexspace can help provide access to (along with booking support and budget management) for desk spaces, meeting spaces, conference rooms, and more—basically, any on-demand space for your coworking needs. Whether you’re connecting with your team on a monthly basis or offering your employees the opportunity to collaborate and work outside their home on a daily or weekly basis, Flexspace can help support the success of your remote team. 

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