6 Critical Skills for Remote Work Managers

Published June 19, 2023
remote work managers

Failure to adjust practices for managing remote employees is one of the biggest sources of frustration we see in remote and hybrid companies. What remote work managers are facing isn’t business as usual and it requires a shift in both skills and thinking. 

If technology has enabled a mass adoption of remote work, it's clear that logistics aren’t the issue. According to Jack Niles, legendary initiator of modern remote work, lagging management practices are. 

We’ll examine six critical management upskills that your remote workforce needs in order to maximize success.

Critical Skills for Successful Remote Work Managers


What is the primary responsibility of a manager? At a basic level, we might say that they exist to make sure work gets done, gets done right, and gets done on time. The tactics often employed to achieve these goals can wreak havoc when translated to a digital workspace. 

In-office tactics that are failing remote workers

  • Desktop drop-ins: The tactic of using presence to apply the pressure that a manager believes will encourage better performance from employees. In a remote work environment, managers who are “checking in” on remote employees throughout the day are creating more distractions for workers who are already struggling to prioritize the incoming messages and notifications in a buzzing digital workspace. 
  • Artificial deadlines: Creating an arbitrary schedule for a task to be completed. This tactic can create undue pressure for a worker who is managing more than one task, making it difficult to prioritize tasks and execute against tasks that are truly pressing. More concerning is the risk of eroding trust between employees and managers, which is a pillar of a healthy workplace.
  • Micromanagement: Controlling the execution of a project in hopes of controlling the outcome. This sometimes manifests itself in remote workplaces with the use of apps that monitor employees’ activity. Tracking keystrokes, mouse clicks, ‘active status’ time in Slack, screen monitoring, or even video recording workers during working times, a tactic used by 1 in 3 remote employers. The negative impact this has on employee experience is a real consideration. 3 out of 5 employees report feeling stress and/or anxiety about their employer surveilling their online activity according to this survey.

Rather than viewing management as a tool to force productivity, successful remote work managers look for ways to empower their team members to do their best work. Managers that intentionally serve to unblock employees, protect their focus time, and focus on outcomes are more likely to succeed. Sharing productivity hacks, encouraging brain breaks, and reducing interruptions are just a few of the ways a great remote manager can help their teammates. 


​​In Oyster’s recent Employee Disillusionment Report, Yen Tan, co-founder of remote worker wellbeing startup Kona, is quoted. ”We’ve studied 1000 remote managers. The best have one thing in common. They ask, “How are you?” and actually mean it. These leaders want to know how you’re feeling, how your kid was up all night with a fever, or how excited you are about buying a new house. If COVID-19 taught us anything, it’s that we can’t keep pretending that life stays completely separate from work.”

Empathy is the ability to connect with others through an understanding of their thoughts, perspectives, and emotions; and demonstrating that understanding with intention, care, and concern. It’s clear from the study that the most successful managers exhibit true empathy. Treating the personal side of work as obligatory won’t create the sense of trust and safety needed for employees to do their best work. 

In today’s workplace, empathy isn’t just a nice to have. It’s a non-negotiable for successful leadership. Here are a few statistics from Catalyst’s’ research that bear this out in a compelling way.

Empathy by the numbers

  • Innovation. When people reported their leaders were empathetic, they were more likely to report they were able to be innovative—61% of employees compared to only 13% of employees with less empathetic leaders.
  • Engagement. 76% of people who experienced empathy from their leaders reported they were engaged compared with only 32% who experienced less empathy.
  • Retention. 57% of white women and 62% of women of color said they were unlikely to think of leaving their companies when they felt their life circumstances were respected and valued by their companies. However, when they didn’t feel that level of value or respect for their life circumstances, only 14% and 30% of white women and women of color respectively said they were unlikely to consider leaving.

The good news is that empathy is a skill that can be learned, practiced, and developed. If you’re managing people in 2023, empathy must be a tool in your belt.


For remote workers, much of the work is done In a silent workspace. Outside of video meetings and the notification sounds reminding workers of mentions that are piling up across their communication tech stack, working remotely can be quiet. 

When we hear the word listening, we often think of verbal communication, using our ears to understand the sounds being communicated. For managers in a digital workspace, listening means so much more. What is being communicated without being said?

Here’s an of example of how a remote manager might listen well.

A colleague who rarely misses deadlines has been late on a couple of tasks this week. They also arrived a few minutes late to a weekly team meeting where they had little to say. You notice they haven’t been very active in Teams/Slack for a couple of weeks, which also seems out of the ordinary. You’re not worried about the tasks or the meeting attendance, but you’ve noticed a change in the pattern. 

Listening is all about noticing. Seeing what isn’t being said and taking notes. We’re not talking about assigning value to your observations, but rather being aware and being curious. 

This leads us to our next remote management super skill


In an office space, you can sometimes see the frustration or desperation written all over the face of a colleague. In a remote team, you might never see the face of your colleague, especially if they keep their video off during Zoom calls. Remote management calls for proactivity. 

As we outlined above, a manager with excellent digital listening skills has a healthy dose of curiosity but it takes proactivity to take things any further. One way proactivity manifests itself in a digital workplace is through a weekly one-to-one meeting between a manager and a direct report. 

When casual hallway, desk-side, watercooler, and lunch break conversations aren’t happening, it’s critical to have dedicated time for a one-on-one conversation. There are four elements to successful 1:1 meetings that should ring true.

Four Elements of successful one-on-ones

  • Predictable. You and your teammate know the meeting is happening. It’s a priority. It might not be the same exact time every week, but it happens with regularity, and it's something you both plan on and look forward to. 
  • Personal. “If you can’t talk about puppies, you can’t talk about profits.” To quote Laurel Farrer, Principal Strategy and Operation, Workplace at Gitlab. Intentional curiosity and conversation about personal life drive a greater sense of connection. Lack of personal connection at work is a primary complaint of remote workers and studies show that it costs companies at least $520 per person each year in absenteeism, lost productivity, and turnover.
  • Purposeful. An organic conversation is great, but there’s something important about having a reason behind your meeting and making sure you get those things covered. Facilitating purpose with a running agenda document that has intentional questions is a great tool for remote managers. Questions like, “What’s going well this week?”, “What’s giving you the most trouble?”, and “How can I help you reach your goals for this week?” are a great place to start.
  • Protected. A 1:1 meeting should be a space that is safe and confidential. When direct reports share their struggles, whether they’re personal or professional, they should feel secure knowing that the information is in a vault. The more trust that is built between colleagues, the more openness will abound, and the more effective a leader can be in coaching their people through difficult situations. 


During the peak of the ‘quiet quitting’ wave, which continues to be a reality in many workplaces, Barnaby Lashbrooke of Time Etc., made the bold move to replace managers in his company with coaches

“Like managers, coaches are still there to act as a first port of call when challenges arise. But instead of directing from above, the focus is on empowering and supporting the employee to find their own way forward.”

In other words, the coaching skill shifts managers from telling people what to do to help them discover and leverage their own strengths to navigate the problems they face.

Think about how this might look in the context of performance reviews. 

One thing we know about performance reviews, almost nobody likes them. Instead of treating them as feedback dumps where a manager tells their reports what behavior was bad and to stop and what behavior was good and to do more of, look at them as opportunities to celebrate successes, set new goals, and encourage team members to stretch beyond what they think they can do. Sounds like a job for a coach to me. 

Have you ever seen a professional sports coach wait until the end of a game to give constructive feedback to a player? Never! Coaches don’t wait, they keep feedback on a continuous loop and find ways to unlock the best of their players. A manager-coach should take the same approach, making periodic reviews (quarterly) something that everyone looks forward to instead of dreads.


Last but not least, clarity. Clarity sounds more like a quality or a virtue but the skill needed here for remote managers is all about writing the unwritten rules of work for their team. 

Have you ever broken an unspoken rule without realizing it, only to be completely embarrassed when you found out, and wished someone had told you and spared you from the humiliation? 

Great remote managers create clarity of expectations, give the context needed for effective decision-making, and operate from a reliable single source of truth. No one wants to be caught off guard because they didn’t have these things in place before moving forward. Managers who give these things create a safer space for the team members to move quickly.

I’m an advocate for creating clarity at the company level as well as among individual teams. Remote work managers may consider creating a charter document for their team that outlines some key guidelines for working together and communicates important information about each team member. 

  • Preferred Communication Styles
  • Greatest individual strengths and weaknesses
  • Timezone and real-time availability 
  • Background/experience for each team member that could be helpful
  • Guidelines for daily check-ins

Creating a charter document is an eye-opening experience as teams learn more about each other and put words to the unwritten norms.

Building the Skills for Remote Work Managers 

In today's remote and hybrid work landscape, it is crucial for managers to adapt their practices and develop the necessary skills to effectively lead their remote teams. Failing to do so can result in suboptimal management practices that hinder productivity and employee well-being. If you want to maximize the success of your remote workforce, I encourage you to explore upskilling your management team with the critical skills for remote managers outlined in this article. 

Want to go deeper into these skills and gain more actionable insights? I invite you to get in touch with us. We offer live training webinars and in-depth workshops on these topics, where you'll have the opportunity to learn from experts and engage in meaningful discussions with experienced remote managers. Together, let's unlock the full potential of your team and revolutionize the remote working experience.

remote work managers

Photography by Sophia Jené Photographs