Goodbye Water Cooler Chats: 4 Chicago Companies Work to Create Virtual Connections

Remote-first companies are reimagining team traditions and getting creative about fostering fun.
Written by Olivia Arnold
July 27, 2022Updated: July 27, 2022

Every other week, the #donut Slack function pairs Ascent employees with a colleague from a different team for a 30-minute virtual chat. The chat has an important rule: They can’t talk about work. 

During one of these #donuts, Gigi Klotz, a sales development team lead, found herself matched with Founder Brian Clark. In just a half hour, she learned that he loves meditation, and the two bonded over their NFL teams’ rivalry. 

Companywide initiatives to foster interpersonal connections — like Ascent’s biweekly #donut chats — are becoming increasingly common as workplaces shift to remote-first settings. For some companies, the days of sharing weekend updates by the coffeemaker on Monday mornings, gathering in dazzling in-office centers of community such as game rooms and stocked kitchens, or celebrating team victories at the local bar on Friday nights are in the past. Instead, leaders are reimagining team traditions and getting creative about how to foster belonging in the remote workplace.

Instilling fun and joy in the workplace is important, but the need to improve remote-first team culture goes deeper. While many employees enjoy the flexibility and freedom that remote life affords them, working virtually can leave people feeling isolated and disconnected from their colleagues. It’s also challenging to cultivate trust and collaboration — important hallmarks for innovation — on a team that has never met in person. 

A 2021 study published in the Nature Human Behaviour Journal found that remote employees communicated less frequently with people outside their immediate teams than in-person workers, and spent 25 percent less time collaborating across groups. 

Four Chicago-based companies are leveraging virtual platforms to foster belonging and collaboration at their workplaces. Some initiatives are purely fun, like virtual game nights and happy hours; others are more intentional about sparking connections, such as remote one-on-ones with supervisors or colleagues; and then there are moves meant to recognize strong work performance, such as accolades in all-hands meetings and coworker shoutouts that transform into gift card credits.

Regardless of their diverse approaches, these workplaces have navigated challenging paths to growing positive remote cultures. Along the way, many teams realized that their beloved in-person rituals did not always translate well in virtual spaces, and they grieved the loss of company traditions and casual “water cooler” encounters. 

The move to remote-first workplaces, however, also expands possibilities for team communication and cooperation. That same 2021 Nature Human Behaviour study found that remote workers spent more time communicating with their immediate team members compared to in-person counterparts. Some companies also continue to organize in-person meetups — such as volunteer opportunities, happy hours, DEI activities and more — as a means to strengthen remote collaboration. 

Built In sat down with leaders at these four Chicago-based workplaces to discuss their challenges and successes when it comes to building connected and collaborative virtual-first companies. 

 

Yello team video call
Yello

 

Jen Meza
SVP, People • Yello

 

As Yello transitioned to a remote-first workplace, the talent acquisition software company found that some of their traditions, like Wine-down Wednesday, felt stilted on Zoom, while other virtual celebrations, like their annual Drag Queen Bingo for Pride Month, were still rewarding. Stressing the importance of intentional communication, the HR tech company says it relies on Slack as an important tool for sharing everything from the CEO’s weekly sales updates to cute photos of employees’ pets.

 

What is the biggest challenge to establishing a virtual-first company culture? How are you overcoming that challenge?

Pre-pandemic, we had a very strong office culture and less than 10 percent of our employees were remote. Today, we have employees in 19 states and 40 percent of Yello employees are outside of Chicago. As we moved to virtual-first, the biggest challenge was letting go of or reimagining some of the cornerstone connection moments that happened in the office. 

There were some things that we had to accept would never come back, and that was hard for people who’d worked in the office for years. On the other hand, about half the people at Yello today have never worked in the office, so holding on to some of those traditions was alienating them. What we focused on as we made the transition was preserving and continuously cultivating a culture of transparency, care for each other and inclusion.  

Some things, like Wine-down Wednesdays, felt forced on Zoom, and we ultimately let them go. Other things, like our annual Drag Queen Bingo for Pride Month, worked beautifully virtually.

What we focused on as we made the transition was preserving and continuously cultivating a culture of transparency, care for each other and inclusion.

 

What’s your number one tip for fostering connection and collaboration among virtual teams?

Be intentional about communication. When we were in person, we relied on pulling together a quick huddle or grabbing people in town halls to share updates. Now, we’ve become much more thoughtful about making sure that information is shared in channels that everyone can access. As a result, our communication is not just more intentional, but also more transparent and inclusive.

At Yello, we bookend our weeks with company all-hands meetings every Monday. The nine-minute meeting is a quick hit of what you need to know for the week. On Fridays, our CEO shares an update in Slack on where we are with sales and renewal numbers, product releases, initiatives, customer updates and the market. 

We also decided that we still want to create spaces for people to gather in person if they want; some folks come to the office one day a week to see each other, some do in-person volunteering together in cities where we have five-plus employees, and we fly everyone to Chicago twice a year so we can meet and connect in person.

 

What remote working tools do you lean on to reinforce culture?

We used Slack before moving to remote first, but it has been the most crucial tool for helping people connect to each other and feel connected to Yello. From a channel for product updates to a channel for pet pictures, there are tons of ways for people to share information and be their authentic selves. 

I’ll also give a shoutout to Guru, which our director of enablement implemented as a single place where we store all of our product, company and HR information.

 

 

Zenobia Moochhala
CEO • Sittercity

 

Sittercity, a childcare provider platform, prioritizes an open-door culture and employee wellness by setting up regular check-ins where people can share with their managers how they’re doing and provide feedback on the company. To promote fun and joy, employees gather virtually for small-group lunches, happy hours, games and more. 

 

What is the biggest challenge to establishing a virtual-first company culture and how is your employer overcoming that challenge?

We quickly moved to a remote model at the beginning of the pandemic. While we worked together to establish virtual-first best practices and adapted to the model, there are still challenges. It’s tough to get a sense of how employees are feeling behind a screen. There’s a lot you can pick up on with in-person interactions that you won’t get in a virtual-first environment. 

Now more than ever, employees are vocalizing what they want out of their workplaces. At Sittercity, we prioritize regular check-ins to understand what’s working well and where we can improve overall. It gives employees the space to share how they’re feeling, and no topic is off limits. Our open-door culture also gives managers more insight into how employees are doing and feeling.

The number one driver of company success is the employees who make the magic happen, so it’s important that employees feel taken care of and appreciated.

 

What’s your number one tip for fostering connection and/or collaboration among virtual teams?

By now, it’s common for remote-first companies to host events online, like virtual happy hours, games, team lunches, etc. If you want to foster connections among virtual teams, you have to create a sense of belonging and community for employees. The number one driver of company success is the employees who make the magic happen, so it’s important that employees feel taken care of and appreciated.

 

What remote working tools do you lean on to reinforce culture?

It’s challenging to get to know your teammates through a computer. While in person, employees can have side conversations that really make a difference. We work hard to recreate what you would experience in an office by using our internal communications platform. For example, during Employee Appreciation Month, we had a different channel for activities, events and mental health resources. We also have channels specific to interest groups and topics where people connect virtually while going about their day.  

My favorite activity is hosting virtual monthly small-team lunches with employees. It builds strong relationships and trust with the team, which is so valuable when creating a supportive culture.

 

 

Julie Gurican
Senior Director, People • BenchPrep

 

Leaders at BenchPrep, a test prep and online learning provider for customers like ACT and McGraw Hill, know that building a remote culture requires intentionality and buy-in from all team members. The edtech company creates community through a number of initiatives, including hosting fun virtual events, sponsoring Grubhub lunches and sending pics of their favorite ferns and snake plants in the #plantbabiesofbenchprep Slack channel. 

 

What is the biggest challenge to establishing a virtual-first company culture? How are you overcoming that challenge?

We had a pretty special in-person culture pre-COVID-19, so we needed to grieve our past and then embrace the future. We got there through trial and error, and learned that what happened in-office didn’t always translate well to virtual. Moving our monthly birthday happy hour celebrations to Zoom — with 100 people on mute and no emcee or structure — just didn’t work; so we scrapped it. 

Instead, we experimented with different remote events — to the tune of magicians, an animal farm tour and board game nights — and added in new ways to replace the “water cooler” with Grubhub luncheons (with smaller breakout rooms and conversation starters) and coffee catch-ups to deepen relationships one on one. 

We also defined what was important to us in our remote culture and created five anchor principles, which helped set the framework for our remote culture at BenchPrep. One of those pillars is to work with gratitude and recognition. We doubled down on sending accolades and shoutouts (formerly in all-hands meetings and casually on Slack), which has really helped with morale and overall happiness.

 

What’s your number one tip for fostering connection and collaboration among virtual teams?

Remote culture takes intention! Culture seemed to come so organically and effortlessly in the in-person world. In the remote world, culture can be just as rewarding, but it takes thoughtful intentionality from everyone on the team — not just the people team or leadership.

Part of organic culture in the in-person world was the over-the-shoulder conversations you heard when you were new. Our Zoom one-on-ones for new hires help create relationships from the get-go when employees join, so they can meet people on the front end of their journey. The team is also known to hop into a Zoom room while doing end-of-week tasks and reporting, to have some fun while wrapping up the week. 

In the remote world, culture can be just as rewarding, but it takes thoughtful intentionality from everyone on the team — not just the people team or leadership.

 

What remote working tools do you lean on to reinforce culture?

We use Slack for work and collaboration, but also for banter and fun — my favorite channel is #plantbabiesofbenchprep. We also started to use Slack’s voice-only Huddle function for quick live convos and to avoid video fatigue.

 

 

Ascent group photo
Ascent

 

Gigi Klotz
Sales Development Team Lead • Ascent

 

Leaders at Ascent, a compliance automation solution for highly regulated industries, emphasize the importance of establishing clear communication with boundaries that are respectful of work and home life separation. The company also uses tools such as Slack Huddles and Motivosity to encourage teamwork and celebrate wins. 

 

What is the biggest challenge to establishing a virtual-first company culture? How are you overcoming that challenge?

Establishing virtual-first company culture is challenging, even more so when your team is spread across numerous time zones. It is challenging to connect with individuals who aren’t on your team in a casual way; ”water cooler” talk has disappeared, and it sometimes feels silly to schedule a conversation. On top of that, how can you build trust and teamwork in your department with people you have never met in person? 

Ascent seeks to fill this gap in multiple ways. We have monthly all-hands meetings where the company gathers to give updates (not just from the executive team, either!); weekly reminders on our #community-random channel to share pictures of pets and family; and, my favorite of all, utilizing the #donut feature in Slack. 

Every other week, #donut randomly pairs you with someone in a different area of the business, matches up your calendars and finds 30 minutes for the two of you to talk about anything except work. These chats allow me to build relationships with people I rarely, if ever, interact with. I’ll never forget my first #donut with the founder of our company; I learned that he loves meditation, and we bonded over our NFL rivalry.

 

What’s your number one tip for fostering connection and collaboration among virtual teams?

My number one tip in fostering collaboration is communication, but with boundaries. In a virtual team, it can be easy to send messages after work hours because the separation between workplace and home has evaporated. Utilizing tools like schedule-sending messages and offering a verbal conversation instead of direct messaging creates a stronger sense of trust between colleagues. 

Additionally, scheduling time for recurring one-on-one meetings between you and your manager helps create a virtual open-door policy where transparency and communication are healthy habits. Having recently stepped into a role with some managerial responsibilities, I consistently focus on fostering teamwork and celebrating highs, lows and everything in between. 

Another way we enhance virtual collaboration is by offering in-person events on a monthly, quarterly and annual basis. This in-person time strengthens our culture, as it consists of volunteering, happy hours, DEI events and more.

Scheduling time for recurring one-on-one meetings between you and your manager helps create a virtual open-door policy where transparency and communication are healthy habits.

 

What remote working tools do you lean on to reinforce culture?

My favorite tool is Slack. Slack allows me to succeed individually and within my team. We celebrate successes, share our failures and jump into conversations instantly with the Huddle feature. Huddle serves as a virtual “water cooler” because you don’t have to schedule a Zoom meeting. It is also great to be able to look back at channels to gain insight into company happenings, team planning and communication styles. 

We additionally utilize a tool called Motivosity. Every month, each employee receives credits on Motivosity that we can send to coworkers with notes of praise in correlation with our company values. Each time a coworker celebrates another, the notification is pushed to Slack in our #community-thanks-and-praise channel. That channel serves as a place where gratitude is expressed, achievements are highlighted and employees are rewarded. Credits received can be put toward gift cards to numerous stores. Expressing gratitude contributes to the trust, communication and collaboration necessary to maintaining a welcoming company culture. 

 

 

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