How the era of the remote worker complicates management

How do you manage a team when you don’t know exactly what they’re doing or where they are at every given moment?

How the era of the remote worker complicates management
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New York-based startup Muck Rack is a team of 50 people who can work from home whenever they want. About one-third of the company’s team is based outside New York and therefore, always remote. CEO Greg Galant says he set Muck Rack up to be a completely remote company, meaning that if the startup’s building burned down tomorrow, business would go on as usual the next day.


“My friends always say to me, ‘How do you know if anyone is really working?’ and I always ask them, ‘How do you know if anybody is really working if they are at the office?'” says Galant. “Because the reality is, you can see somebody at their desk and they can stay late, but that doesn’t mean they’re really working.”

As flexibility in the workplace increasingly becomes the most sought-after work arrangement, we see companies scrambling to put a flexibility policy on the books. What ends up happening in the fluid workplace, though, is that workers have more autonomy, which ends up complicating management. After all, how do you manage a team when you don’t know exactly where they are? All of this is further complicated when you consider the diversity of the workforce and the reality that we have five generations working side-by-side who need flexibility for a variety of reasons.

“We expect more of [workers],” says Ed Barrows, managing director at Duke Corporate Education. “We text, email, and communicate globally around the clock. If that is the case for a working environment, you’re going to run into people’s personal lives.”


Of course, all of this change requires managers to manage differently, and the new nature of employment relationships can feel intimidating. However, “When companies are able to do this, they’re really in a position to tap talent,” says Barrows, coauthor of the book Managing Performance in Turbulent Times. Below are steps organizations take to manage remote workers more effectively:

100% buy-in from leadership

In order for a system to work, everyone needs to buy into it, especially upper management. According to Galant, one of the most powerful things a leader can do, if they want a remote culture, is to work remotely themselves.

“That could mean working from home one or two days a week to set the tone and show people it’s possible,” he explains. “If the CEO and the top people in the company always show up in the office five days a week, then you can say you have remote culture all you want, but actions speak louder than words.”


At Muck Rack, employees can work from home whenever they want without having to request permission because doing so would imply that there is “something wrong or inferior about [remote working],” Galant says.

When Agios Pharmaceuticals implemented a flexible work environment, the company got buy-in from management by sharing success stories of how a flex culture makes the biotech better, and how meeting people’s needs help productivity and teams, says Melissa McLaughlin, chief people officer at Agios.

When O’Melveny & Myers LLP introduced flexible options for its staff attorneys, counsels, and associates, the international law firm made sure to include its partners. Mary Ellen Connerty, who leads diversity and inclusion at O’Melveny & Myers, told Fast Company in December 2018 that the company “didn’t want this to be an associates and counsel issue, but a shared issue and go under the bigger umbrella of well-being.”


Being aware of people’s time (especially remote workers)

If managers are adhering to traditional management practices, they’re going to feel anxiety with remote teams. They’re going to want to check in constantly to make sure people are working. But checking in constantly prevents work from getting done.

Robby Macdonell, CEO of RescueTime, says this threat is even more prevalent in a remote work culture because people can’t see that someone has their head down working. You can’t see that they have their headphones in and are in deep concentration.

“That innocent ‘Hey, do you have a minute’ is one of the most dangerous things that can happen,” says Macdonell. “It’s never just a minute. There’s always effort to get back into something.”


Since every employee at RescueTime works remotely, the team relies on communication streams, but having these channels up and running constantly can be disruptive, warns Macdonell, so his team shares their work status in the workflow tool Slack to communicate with one another.

The company is currently experimenting with ways to integrate RescueTime’s time management software into Slack so work statuses can be automatically set. For instance, if RescueTime’s tool picks up that you are working on something at the moment, it can automatically notify colleagues in Slack that they should not message you.

“[Slack] is a good way to see the pulse of your remote team,” says Macdonell, and “see how the interactions are going there even if they’re not work-related.”


Having regular scheduled meetings

One disadvantage of a remote team is that there are no chance meetings that lead to unplanned brainstorming sessions and conversations that lead to innovative, groundbreaking solutions.

So in order to make sure collaborations still occur and employees have the environment they need to further refine or develop the next great idea, RescueTime relies on regularly scheduled meetings.

At Muck Rack, aside from regularly scheduled meetings where colleagues bounce ideas off one another, there is also a regularly scheduled weekly meeting meant to build team morale and culture. In the meeting, everyone shares a “win” they had during the week. It creates a kind of culture, says Galant, and it also informs teams what their colleagues are working on.


Always including a video link to meetings

Having a flexible work culture means it’s always a possibility that someone is working remotely. Don’t wait until after a meeting has started to figure this out. Instead, be mindful of everyone’s time by making sure that a video link is curated for every scheduled meeting.

“One thing we struggled with at first was starting a meeting,” says Galant. “Sometimes you wait until the meetings start, and then you figure out how to connect everybody. It would always be a mess.”

Additionally, a video link means being able to see everyone’s face, which makes a big difference, says Galant, because you get a sense of when somebody wants to jump into a discussion or has a point of view they want to add.


Taking the time to include the big picture

In remote work cultures, it’s easy to get caught up in the logistics–giving people the information they need to carry out a task, then checking back in to discuss the task in more detail at a later date.

What easily gets lost is the big picture–why someone is doing something or carrying out a task. Whether someone is working remotely, freelancing, or is a temporary worker, understanding the meaning behind your work is key to good performance, and it pushes people to go the extra mile.

“The biggest pain point for me is keeping the vision of the company,” says Macdonell, and “driving everybody toward the North Star, keeping that front and center.”


Taking isolation seriously

The lack of social interaction (think: no small talk from running into each other by chance in the office) can get lonely, and eventually, wreak havoc on the body and mind. This is especially dangerous during the colder seasons when people tend to stay indoors more.

“It’s something that can creep up on you because you have this proxy of communication and you are talking to people every day,” explains Macdonell. “Maybe not verbally, sometimes just through typing, but it wears you down after a while.”

Macdonell urges leaders with remote teams to take mental health seriously and commit to reaching out. By nature, humans thrive on social interaction, and the brain is healthy when we have people to interact with regularly.


“If you’re not seeing people face to face, you’re going to miss some cues that somebody is not having a good experience,” says Macdonell, “and we want our employees to have the best work experience that they can. From that standpoint, I want to be aware of those things, but also on a human level, I want to be aware.”

Suffering from loneliness is not an easy thing to communicate for anybody, so the onus is really on team leaders and senior managers to reach out.

“A lot of time, people don’t bring that stuff up because nobody asks,” says Macdonell.


One thing you can do is be up front about why you’re asking. You can say it’s on your mind because the colder months are here and it’s easy to become isolated. Macdonell says it’s been helpful for him to be open and honest with his team when he is starting to feel lonely and to talk about mental health openly. This way, he is communicating with his team that it’s safe and appropriate to bring up these topics.

Being aware of distance bias

Distance bias is the brain’s tendency to think that people who are physically closer are of greater importance or value than those who are further away. It’s essentially out of sight, out of mind. This phenomenon means that remote teams end up feeling alienated.

“It seems to be a problem in decision making and collaboration,” says Macdonell. “You should assume that a dial-in on a conference line is not a seat at the table.”


Defaulting to video chat, or, as a manager, remembering to check-in with your remote team can make the remote experience richer.

“When it comes to talking about the decisions that need to be made, giving input, being in a full, first-class system in equal collaboration, [remote workers are] at a big disadvantage,” says Macdonell. “Awareness is a good first step. Know that that disadvantage exists, and find ways to mitigate it.”

As the nature of our employment relationships continue to change, it’s up to organizations to not only make the necessary changes but also give managers the tools needed for those changes to be successful. For instance, if the new rules require managers to “manage” less and “empower” workers more, what does that look like? And what does that mean for a manager’s day-to-day?


About the author

Vivian Giang is a business writer of gender conversations, leadership, entrepreneurship, workplace psychology, and whatever else she finds interesting related to work and play. You can find her on Twitter at @vivian_giang.