10 CEOs explain how to compassionately communicate from a distance

It’s possible to build rapport remotely. Find out what’s working for business leaders navigating this new territory.

10 CEOs explain how to compassionately communicate from a distance
[Photo: youssef naddam/Unsplash]

The number of remote workers has climbed steeply since the start of the COVID-19 crisis. According to a recent Gallup poll, 57% of workers now say their employer is offering a remote work option, up from 39% previously.


For many CEOs, this means suddenly leading teams from a distance, at a time we need to be deeply connected. 

Communicating real compassion through your screen is hard. But it can be done. I’ve learned this from my own experience. And it’s been reaffirmed by connecting with these 10 CEOs, who share how they’ve struck the right balance. Here’s what’s working for them: 

Lean in, literally

Body language and facial cues typically tell people you care. Of course, that’s watered down via videoconferencing. But there are some workarounds. 

“Emotional nuances are not easily communicated in the digital experience. But lucky for us, humans can use their imagination to bridge these gaps,” explains Analisa Goodin, founder and CEO of Catch & Release, which sources and licenses user-generated content from the internet. Listening deeply, leaning into the camera, asking more questions, and showing great follow-through are all signals that you care.

Be realistic

 “In light of COVID-19, if you are worried about productivity versus people, you are worried about the wrong thing,” says Mike Massaro, CEO of the fintech Flywire. “Of course things will be less productive in this new world, but longer term that will solve itself. Focusing on the wrong things will ultimately have you miss a massive opportunity to engage your teams at a personal and deeper level.”


In that vein, he is choosing to show compassion in a number of ways, including flexibility—for himself and his team. 

“Know that every day of remote working will bring a new challenge to your team,” he says. “Many people will need to adapt their work schedules to support their families or other responsibilities. Accommodating these revised schedules and being open to flexible working hours will keep your team engaged and productive.” 

Prioritize connection

With stress levels through the roof, group check-ins can be a great way to show your team that you care about their emotional well-being. 

One thing we’ve been doing as a team is playing “Rose, Bud, Thorn” on Zoom every Friday. . . . You share the most challenging thing that happened the past week, the best thing that happened, and something you’re looking forward to for next week,” says Claire Schmidt, CEO and cofounder of All Voices, an anonymous reporting tool employees use to report harassment or bias to their leadership. 

“Personal anecdotes are encouraged,” she says. “For example, one person on our team had to cancel her wedding. Giving people that structured space to open up and share about whatever is happening in their lives allows us to connect as people, not just as colleagues.”


Dig deeper

Managers typically have one-on-one meetings with their direct reporters. But during this pandemic, managers should also use those calls to make a human connection, according to Enrico Palmerino, CEO and founder of Botkeeper, automated bookkeeping support for businesses.

“It’s important to take time during each check-in to see how everyone’s doing overall,” he says. “For example, what did they do over the weekend? How’s the family? What’s excited them lately? This helps signal that you’re listening and you care about them on and off the clock.”

Be open

That old-school business mentality, of the ‘big boss’ who leads his team through an emotionally disconnected management style, is so outdated,” says David Shove-Brown, cofounder and Principal of //3877, a boutique architecture and planning firm. “Leadership is about creating and maintaining a two-way street of open communication.”

For him, that has meant finding a way to connect with his team in deeper ways, even though he can’t do it in person.“Last week, we sent out a company-wide email that wasn’t necessarily about the company itself, but rather about reminding our team that we’re a community, and part of something bigger than current world events,” he says.

Mirror your office culture 

When teams are working in person, it’s easier to keep your team connected. But when you’re working remotely, it’s much easier to inadvertently leave someone out of the loop. There are workarounds, says Christopher Auer-Welsbach, c0-CEO and cofounder of Kaizo, a performance management platform for customer support teams. 


“There are a few obvious ones, such as pushing for calls rather than emails,” he says. “Less obvious elements are to conduct more ad-hoc calls than scheduled meetings to keep people alert and mimic the office-like ‘quick question’ culture. [This can nurture] creative moments and quick decision-making.” 

Ishveen Anand has also found ways to preserve the company culture she’s built at Open Sponsorship, the largest marketplace for sports sponsorships. She initially considered dropping her one-on-one check-in meetings with her team during this remote work time, but quickly realized that would be a mistake. “I realized the one-on-one meetings ensure that I hear how the team is doing work-wise and mentally,” she says.

Put on their shoes

Before you can understand how to show someone compassion, you first need to understand where they’re coming from, says Antonio Pellegrino, the founder and CEO Mutable, a Microservice Platform-as-a-Service. 

He says he often does that by looking for common ground with clients. “I’m sure many of them are stuck trying to save their companies with their kids bouncing off the walls. I can relate to that,” he says. “When I’m on a call with a client, I start by sharing what I’m dealing with, so they’re more comfortable opening up about their own issues. It helps us bond over shared adversity.”

Be open

“Communicating compassionately in a time of uncertainty is all about being clear and consistent,” says Jay Reno, founder and CEO of Feather, a furniture startup subscription. “Early on, our leadership team at Feather made a commitment to share company news and updates with our entire staff on a daily basis, so that everyone would feel that they’re up to speed on business operations.” 


Joanna McFarland has also embraced transparency as the cofounder and CEO of HopSkipDrive, a transportation service for children used by schools and families. She says being forthright invites compassion, especially during hard times. 

“I’m fully transparent about what’s happening, the context and decision-making process, and what will happen to the best of my knowledge,” she explains. “If I don’t know, I say I don’t know. I don’t put on a show. If I’m emotional and it’s been a tough day, I show that. I think vulnerability engenders compassion toward my team, and I see them show compassion toward me in turn.”

About the author

Beck Bamberger founded BAM Communications in 2008 and writes regularly for Forbes, Inc., and HuffPost about entrepreneurship, public relations, and culture.