The New Playbook
for Executive Leaders
Today’s CEO

How Leaders Make Remote Work Succeed

In this article:
Spontaneity, empathy, and reading the (virtual) room have helped CEOs keep their teams engaged and connected during an unpredictable year that separated colleagues and posed management challenges, but also offered insights into new ways of working and leading.

There wasn’t a lot of time to come up with a rock-solid plan for how to lead a remote workforce when the pandemic hit. CEOs, like everyone else, went into an entirely new mode of working, leading their teams through a year like no other without a playbook or a crystal ball.

One of the biggest shifts was the sudden transition from in-person offices to remote work. No more spontaneous check-ins, on-the-spot brainstorming, or reading facial cues to detect moods. All that was gone.

“The biggest challenge has been not having that collaboration time to talk with someone on the elevator and get their opinion,” says Michelle Mills Clement, CAE, CEO of the Chicago Association of Realtors (CAR). “What I find with remote work is, you have to force that in. It’s not organic.”

A challenge for Sara Fidler, president of the Maryland Independent College and University Association, was that none of MICUA’s six staffers worked remotely before the pandemic. Fidler was the only one with a laptop.

But her team adapted well—and quickly. Some employees took home a few older laptops that MICUA had on hand, and others opted to use their own computers. Fidler increased the mobile device stipend for those using their own devices. Since September, she has bought a few employees new laptops, funded by an increased tech budget the organization had adopted before the pandemic.

One upside to that rapid shift, Fidler says, has been the flexibility it has given her team members. Employees who wanted to start working earlier shifted their hours, and the stress of sitting in traffic was removed. The flexibility has made her team happier and more productive. “This is time for innovation,” she says.

Despite being connected through virtual meeting platforms, texting, and emails, personal communication has taken a hit, and it’s harder to know when someone is having a bad day because you’re not interacting in person.

Staying Connected

Technology has enabled workplace innovation, but the lack of face-to-face communication has been an obstacle. Despite being connected through virtual meeting platforms, texting, and emails, personal communication has taken a hit, and it’s harder to know when someone is having a bad day because you’re not interacting in person, Mills Clement says.

When she observes an employee’s work starting to fall off, or they are missing deadlines, instead of calling them out for it, she checks in and asks, “Hey, how are you feeling today?” This opens a whole new conversation, she says. Mills Clement has also made spontaneous cellphone calls, without a reason, just to check in.

“The mental health piece is something that can’t be ignored from this whole pandemic,” she says, adding that it’s not just COVID-19—it’s the tension over racial injustice, a contentious presidential election, and financial hardship.

Fidler’s teams stays connected with a staff meeting on Zoom every Monday, which she scheduled for later in the afternoon to give employees some time to “clear out the cobwebs” from the weekend. She asks each of them to give her a topic for the meeting, so they have ownership in the discussions and to encourage more engagement. She also meets with each staff member individually once a week for 30 to 45 minutes.

“There are so many other things going on in people’s lives,” she says. She uses those one-one-one meetings to ask how they’re feeling, beyond just the perfunctory, “How are you?”

Boosting Morale

Mills Clement knew she needed to implement some morale boosters for her team of 42 because of the distance of the remote work environment. CAR has held a virtual wine and chocolate tasting, a lip-syncing contest, and DJ-hosted happy hours. Leading up to Election Day, Mills Clement sensed anxiety on the team, so she spontaneously hosted an “election deflection” happy hour. She closed the office at 3 p.m. and hired a virtual magician. The element of surprise and a little hype around these events help to “pull people out of a potential funk” and provide “upbeat motivation,” she says.

Virtual happy hours aren’t for everyone. Fidler floated the idea to her team but didn’t get any traction. Because many MICUA employees are introverts, she says, she looked for other ways for them to bond where everyone is comfortable. They now have virtual coffee breaks to stay connected and get to know new team members.

Mills Clement says her innate empathy for people helps her respond in these times, and as a mentor she helps others work to develop it. “I feel like if you don’t have empathy, you’re going to fail as a leader,” she says.

A lot of people have learned empathy out of necessity this year, Mills Clement says, adding that it will be important to continue applying those lessons when the world comes out on the other side of these crises.

Lisa Boylan

Lisa Boylan is a senior editor of Associations Now.

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