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The Biggest Remote-Work Lessons Managers Have Learned

A man and his son are sitting at a table with a laptop.

​With millions of Americans working remotely because of the COVID-19 pandemic, managers have had nearly a year of experience with at-home work policies.

And not all of that experience is good.

According to a Harvard Business Review survey, 40 percent of managers and supervisors expressed "low confidence in their ability to manage workers remotely." Another 41 percent of managers doubt their ability to keep their remote staffers motivated over the long term.

"Managing a remote team has been far more challenging than anyone has ever imagined," said David Niu, CEO of TINYpulse, a workplace communications firm in Seattle. "However, it's important to recognize that work from home isn't going away anytime soon."

Niu and other management decision-makers have learned these key lessons:

Lack of human interaction is a bigger threat than originally thought. After months of managing remote workers, Niu and his management team learned that it's extremely difficult to keep the company culture going with no human engagement.

"Satya Nadella, CEO of Microsoft, was right: There's invisible social capital that is built up over hundreds of personal interactions that gets drained as everyone is remotely working," Niu said. "These interactions are so critical to company culture and employee happiness that you have to find ways to instill [them] virtually."

TINYpulse's internal research showed that worker-to-worker engagement has dropped 20 percent on a year-to-year basis, as employees get less face time together.

"Knowing this, we've leaned into it from an executive perspective and have crowdsourced virtual engagement ideas from our teams," Niu noted. "Currently, we now host informal social hours, employee-led yoga classes, informal weekly lunches, a TINYfit club so we can challenge each other to work out, and even online escape rooms. All of these allow us to take a break from work and get back to those casual interactions that all make us human."

Matthew Avary, senior manager of B2B Customer Success at The New York Times, manages a team of nine. He noted that it's easier to pick up on subtleties while working face to face, compared with communicating mostly through e-mail or instant messenger. He tackled this dilemma by scheduling more weekly and monthly meetings, which seemed to be a common occurrence across businesses.

Building social "boxes" should be a priority. "I've learned the more virtual the work, the more structure you need," said Cynthia Spraggs, CEO at Nova Scotia, Canada-based Virtira, a remote-work advisory firm, and author of How To Work From Home And Actually Get Sh*t Done (Advantage, 2020). "We found that you need to build 'virtual' office walls to replace the ones everyone is used to."

This could mean setting up virtual team spaces that bring colleagues together to solve shared challenges raised by working from home. "Are they parents with children at home? Do they have aging relatives in care homes? Are they social animals now locked in by themselves?" Spraggs asked. "By putting these individuals together in team chat and collaboration spaces, you can increase engagement and inclusivity, and at the same time help everyone be more productive at home."

Remote work is a scheduling nightmare. "One thing we learned very quickly was that you can't expect your employees to be on the same schedule as you [if you are] working from the office," said Pete Sosnowski, vice president of people at Zety, an online career services platform in Warsaw, Poland. "Remote work requires us to arrange our work and private time in an entirely different way to handle distractions and manage work/life balance. Therefore, allowing more-flexible work schedules was crucial in managing our teams."

Zety managers limit online presence from 11 a.m. to 3 p.m. each day for scheduled meetings, while letting employees arrange their work outside of these hours as they wish. "The only requirement we have … is the deliverability of goals set for each employee," Sosnowski said.

The remote "burnout" factor is real. For Attison Barnes, co-founder of Captain Experiences, a Galveston, Texas-based fishing-guide company, the biggest factor facing the company was "employee drain and burnout."

"The burnout is easy to see," Barnes said. "You notice a marked decline in the quality of the employee's work and a failure to go above and beyond in their work. If they aren't engaged, they won't give their all to the work."

Captain Experiences is addressing the problem by increasing its scheduling flexibility for employees. It's also leaning on technology meeting tools like Google Meet and Google Calendar to keep employees in the loop.

"In the office, employees have natural breaks during the day where they have informal conversations, or even go to meetings where they don't stare at their screen," Barnes said. "Offsite, it's crazy to expect employees to stare at their computer screens all day nonstop, so we try to allow more-flexible schedules. If employees would rather run an errand during the day and work more at night, we accommodate that and trust the employee to get their work done."

You need to put yourself in your employee's shoes. Managers have had to recognize that remote employees are working in an environment with many distractions they can usually avoid at the workplace. Some people are having to home-school their children, share workspaces with spouses and deal with their pets—all while trying to meet their work quotas. 

Nelson Sherwin, manager of Nebraska-based PEO Cos., an HR professional services firm, said his biggest mistake when first managing employees at home was that his expectations were too high—and his empathy too low.

"I was really unrealistic at the beginning of our remote-work experience," he said. "I expected our employees to fuss a little in the beginning and then just fall into place within a week or two. I didn't have the necessary patience or understanding."

Sherwin is candid in admitting what many managers operating during the pandemic seem to feel: "No one prepared me for this experience," he said. "In many ways, it was the blind leading the blind."

Sherwin committed to changing his views on remote-work realities, learning about what people are experiencing and becoming more accommodating.

"It's not unprofessional to be empathetic," he said. "It doesn't hurt my bottom line to be patient and understanding with people. Extending a helping hand ensures that they'll want to work with me even after the crisis is over, and they won't desperately look for anywhere else to work because I was unreasonable."

Bob Batory, senior vice president and CHRO for WellSpan Health, said his company offers managers a selection of virtual training sessions. Since September 2020, "nearly 150 of our leaders have participated in Leading Remotely 101," he said. 

Not all employees enjoy working remotely. Some employees may be "old-school"—uncomfortable with the isolation of remote work or unacquainted with using technological tools and platforms. Managers have had to learn how to respond to a range of remote-work experiences.  

Avary of The New York Times explained that the majority of his work unit has been with the newspaper for over 20 years. They want to come back to the office, he said, because it's what they're used to and where they feel the most productive.

On the other hand, other remote employees may appreciate avoiding long commutes or the saving money on workplace parking. They may find they're more productive at home because they can better manage their time and avoid workplace distractions that interrupt their concentration.

"It's about knowing what's important to your team members," Batory said. It's about finding out "who thrives with autonomy versus those who need more connection."

Brian O'Connell is a freelance writer based in Bucks County, Pa. A former Wall Street trader, he is the author of the books CNBC Creating Wealth and The Career Survival Guide.

Electa Willander is a freelance writer based in Gettysburg, Pa. 


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