Remote working Guide

Challenges of Managing Remote Employees & Their Solutions

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Challenges of Managing Remote Employees & Their Solutions
Written by
Mayank Bhutoria,
June 18, 2024

Key Takeaways

The year 2020 has seen companies almost fully embrace remote work. 

Today many organizations are remote first or are actively hiring remotely. But how easy or difficult is it to manage remote teams?

A survey report mentions “of those that worked remotely during the pandemic, 78% say they feel more included while returning to office.” In the same survey, 55% of employees mentioned working more hours remotely than at the office. 

So, here’s the question - Are there serious challenges with remote work? 

Let’s discuss remote work challenges for managers and find ways to manage them better. 

Challenges of managing remote employees 

1. Tracking work & productivity

2. Communication and collaboration

3. Company culture

4. Establishing trust

5. Learning & mentorship difficulties

6. Disrupted work-life balance 

7. Difficulty in ensuring tech equity 

1. Tracking work & productivity

Time tracking is one of the major challenges of working from home. As  BBC reports, a Microsoft survey mentions that while 87% of employees feel they are most productive while working remotely, their bosses don't think so. The report mentions that 80% of the managers disagreed. Clearly, there’s a disconnect between the workers and their managers, which needs to be addressed. 

How to overcome?

Implementing time-tracking tools like Clockify and Hivedesk is a common practice for remote managers to gauge how much time employees spend at work. However, Robert Pozen, Author of Extreme Productivity: Boost your results, Remote Inc and teacher at MIT Sloan School of Management, gives a different perspective. Here’s what he mentions in the unSILOed podcast

“a  billable hour system is an input system, and in a knowledge-based economy, the idea that counting the inputs is the way to look at it is just crazy because people shouldn't be congratulated for spending more hours on something if they have a bad result.The only way to get organizations off hours and into a results-oriented output system is to provide them with an alternative system of accountability.”

So, managers and employees can agree on their monthly or weekly deliverables (aligned with the organizational goals) and set a timeline. Once the managers know the timeline and deliverables, they need not micromanage their remote employees. 

At the same time, employees feel more in control and accountable because it doesn't matter how and from where they’re getting the job done, or how long they’re spending on a given task, as long as it is done perfectly. This, in turn, improves employee satisfaction and productivity. 

2. Communication and collaboration

Working with distributed teams across boundaries means an inability to communicate and collaborate face-to-face. Further, working in different time zones remains one of the most pressing remote team challenges. A Buffer report mentions that 62% of people work directly with teammates in different time zones. Another report mentions that 21% of employers say employees must work in the same time zone per their flexible work policy. 

Although communicaiton and collaboration poses remote work challenges to employers and employees alike, over the last couple of years, teams have learned to manage it better.

How to overcome?

According to a report

  • 54% of employers have trained their workers to hold virtual meetings effectively, and
  • 48% mention they have educated their employees on using real-time and asynchronous communication in tandem for better collaboration across time zones. 

Apart from training employees, employers can also do the following to overcome this challenge of managing remote employees: 

Invest in communication tools, 

Use effective project management software, and 

Foster a culture of two-way communication for a more inclusive and collaborative workplace.

In the podcast, The Challenges of Remote Work, 37 signal co-founders Jason Fried and David Heinemeier Hansson share the best possible solution to the time zone difference problem. They mentioned,

“Being a remote organization, 37 Signal stresses hiring employees with a time overlap.” David says, “I think four hours really is the sweet spot for me. So you have your own time where you can get something ready and then you have a fair amount of overlap.

They further suggest that while scheduling meetings, employees and managers must be more mindful of the different time zones their colleagues are in. They also suggest hiring strategically for employers so that there is some timezone proximity between team members. 

Read more about remote work best practices here

3. Company culture

As SHRM mentions, a survey found that 66.5% CHROs and CEOs agreed that maintaining the right company culture was their biggest challenge in remote work. Unresolved conflicts is another challenge of managing remote employees that can arise if the company culture is not set right. 

How to overcome?

Organizations that have been remote from their inception say that it's possible to build the same office culture in a remote setup; it’s just that employers need to pay extra attention and work hard. 

For example, Buffer, a fully remote company, offers its employees reimbursement for co-working costs, unlimited vacation, a minimum vacation policy of 15 days, time off for mental health, and a role buddy to help new hires navigate the workplace. A little bit of additional support is what remote employers need to extend to build a strong remote work culture and navigate any remote work management challenges. 

To address problem related to unresolved conflicts, employers should invest in building a strong company culture. Few things that companies can do:

  • Offer resolution in written so that there’s no miscommunication or speculations.
  • Enforce an open and clear line of communication channel from the onset. 
  • Encourage everyone to share their thoughts and opinion without any fear.
  • Have a proactive approach towards conflict resolution.
  • Gather facts and reports while resoluting a conflict, avoid biases.
  • Follow up even after the resolution has been solved to ensure there are no lingering thoughts.

4. Establishing trust

A survey among 1500 business decision-makers mentioned that nearly 65% of employers do not trust remote workers to do their jobs from home. The survey also suggested that 39% of employers believed their employees do not work as hard when working remotely. 

How to overcome?

While the data looks worrying, trust can be built in remote workplaces with little effort and mindfulness. 

Be clear in your expectations when you adopt a remote work policy. What does remote work mean to you and your employees? Can they work from anywhere, anytime, or they must be present at certain hours of the day for synchronous meetings? Set your expectations. 

Once your expectations are set, communicate them. Regular one-on-one chats, video calls, and team standups are ways to stay in touch with remote employees to help build trust. 

Avoid micromanaging. Instead, set clear goals and expectations. Finally, be supportive and nurture a workplace culture that values each individual. 

5. Learning & mentorship difficulties

Learning and mentorship difficulties is another challenge of managing remote employees, especially with new hires joining the team and needing the initial handholding to understand the work culture and processes in their new workplace.

How to overcome?

37 Signal co-founders Jason Fried and David Heinemeier Hansson had a few insights on pairing employees in the challenges of remote work podcast. They shared, “employees can be paired up based on their organizational experiences.” For example, each new hire can have a senior employee as a ‘workplace buddy’ to help them understand the nuances of the work environment until they get settled. Other means that can resolute the problem are:

  • Creating a culture that values communications and encourages regular check-ins. 
  • Asynchronous mentorship can be an effective way to mentor remote teams.
  • Employers can provide resources and support to help remote teams with learning and mentorship. This can include training for mentors, mental health support, and stress management training.

6. Disrupted work-life balance 

Stress from work is on the rise, and distributed teams are not immune to it. No clear boundary between work and personal life and feeling disconnected from coworkers are two of the top stressors among remote workers. 

How to overcome?

A few things that employers can do to manage this challenge are:

  • Offer flexible work arrangements
  • Encourage employees to take regular breaks
  • Provide resources to cope with stress
  • Respect the team member’s time boundaries
  • Promote asynchronous communication wherever possible

Read more: Hiring Remote employees

7. Difficulty in ensuring tech equity 

One of the major work-from-home challenges is having access to technology compared to their counterparts working from the office. In a report, 36% of employees mentioned that technology is an issue for a distributed team. Not being willing to use personal computers for work, system crash in the middle of the work, and not having access to the necessary hardware and software are some common challenges that remote employees face.

How to overcome?

To mitigate such remote team challenges, employers must ensure that the distributed team has access to the same tech resources as their counterparts working from the office. 

To begin with, employers need to relook at their tech stack and the policy around it to streamline the tech access for both in-office and “somewhere else” workers at par. Employers should also set up a budget for investing in technology that facilitates better communication and collaboration. An ideal distributed team should have access to the following:

  • Communication tools like Slack and Zoom
  • Project management tools like Trello and ClickUp
  • Productivity tools depending on your team’s requirements
  • Expenses tracking tool

Do you aspire to be a remote-first company and build a great remote work culture? Here’s a bonus ⬇️

Check out the process of hiring remote employees in detail here


Our tips can definitely help you build a strong remote workforce. However, hiring cross-border teams comes with challenges, like legal compliance and forex risk during multiple currency payments. 

Moreover, hiring talents take a lot of time and while you’re busy with the paperwork, the talent might get hired by another competitor. But that doesn't mean you must step back from your hiring decision! 

Partnering with EORs like Gloroots can be a great idea as you can hire hassle-free while Gloroots do all the heavy lifting of managing the legal compliances. With Gloroots, you can fast forward your recruitment process. With few clicks you can automate the entire contract generation process. Plus, you need to make only one payment for all employees in your home-currency to the EOR. 

Book a call today to know what Gloroots offers. 

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