28 Remote Team Leaders Reveal the Single Biggest Challenge in Managing a Remote Workforce

The COVID-19 pandemic caused a sudden, massive shift to remote working across many industries. For managers who were used to interacting with their teams in person, this meant a drastic change to their management practices. In some cases, the shift to remote work required changes to the way managers monitor their team’s work, how they collaborate, how they track projects and ensure that their team continues to meet deadlines, how they provide feedback to their team members, and more.

As companies consider a return to the office, some are opting to continue remote work or at least offering their employees the option to continue working remotely. Hybrid work models are being adopted by a growing number of organizations as companies seek ways to satisfy the needs of employees who love the flexibility and autonomy of remote work as well as those who work best in an in-person office environment. That means managers are facing the challenges of managing a remote workforce as well as the typical demands of managing on-site teams.

While remote work remains popular even as organizations have the option to return to the physical office, it’s safe to say that managing a remote workforce poses a variety of challenges. The good news is that it’s possible to overcome many of these challenges, or at least minimize their impact. To learn more about the most significant challenges business leaders face when managing a remote workforce, we reached out to a panel of remote team leaders and asked them to answer this question:

“What’s the single biggest challenge in managing a remote workforce?”

Meet Our Panel of Remote Team Leaders:

Read on to learn what our panel had to say about the biggest challenges in managing a remote workforce and how you can overcome them.

Ryan FyfeRyan Fyfe


Ryan Fyfe is the COO of Workpuls, Inc.

“The single biggest challenge in managing a remote workforce is communication…”

Communication is the lifeblood of any organization, and its absence makes it impossible to gauge the effectiveness of a workforce. Added challenges include not being able to read body language such as posture. How can you tell if someone’s agitated or relaxed? What if they’re arguing about something in private and you don’t know? You can’t tell. This causes an added level of stress that could easily result in disciplinary action when there’s no way for management (or coworkers) to gauge what’s really going on…even though it may be perfectly legitimate/understandable behavior caused by poor timing/communication.

Ifty NasirIfty Nasir


Ifty Nasir is the co-founder and CEO of Vestd. Throughout his career, he has built businesses and led high-performing teams. He is a strong believer in the ‘Ownership Effect’ and advises businesses on how to share equity to incentivize teams and unlock value.

“Vestd went fully remote two years ago, and I think the single biggest challenge has been to remain agile enough to respond to teething problems…”

You might find that your communications system doesn’t quite replicate the back and forth of a lively office, or perhaps quieter team members start to disappear into the background. That’s the challenge—to be looking for those emerging issues and to come up with creative ways to solve them as quickly as they pop up.

After a couple of years of doing this, I wouldn’t run the company in any other way because the benefits for the team are enormous. But it is a work in progress, and you have to be flexible and attentive enough to roll with the shifting landscape of how it’s all hanging together.’

Ann WaltonAnn Walton


Ann Walton is the Vice President of People and Operations at Voices. She has more than 25 years of experience and has an extensive track record transforming human resources & operations from
ordinary to extraordinary by instituting and fostering a high-performance culture. Ann is recognized as an expert in human relations, process engineering, and organizational change management.

“The biggest challenge that comes with leading hybrid and remote teams is ensuring equitable, unified experiences that maintain and uphold our company culture of unity and inclusion…”

Even with the best intentions, those who work in the office will have a different experience than those who do not, so bridging that gap has become an important focus for us.

Some ways we prioritize an inclusive hybrid and remote experience are through being mindful of not equating preference or value to a colleague that works in the office over a colleague that works remotely, offering the same training and development opportunities, measuring skills based on results and not familiarity, and ensuring equal job opportunities are afforded to all qualified employees. This is an area where human resource partners can be especially helpful in identifying potential inequities before they occur.

We also focus on the language we use and remind ourselves that whether a colleague works in the office or remotely, we are one team and one company. Language becomes important in how we classify employees. If we start to hear “them” (remote) vs. “us” (in-office) we need to address and correct it to “us” and only us. Creating inclusive opportunities for team building, ideation, planning, and decision-making and not defaulting to in-office employees because you can see them and neglecting the employees who are only a video call away keeps us from settling into that us vs. them mentality, which doesn’t belong in our inclusive work models.

Sean McPheatSean McPheat


Sean McPheat is the CEO at MTD Training Group.

“The biggest challenge is the loss of all of the informal learning that takes place in an office…”

For example, in Lockdown 1 I was asked questions about 3 times per day by my team, on average. When we came back to the office, I was asked an average of over 20 questions per day. These were instances of picking my brain, running ideas past me, or asking me for creative input. So, what happened to all of these questions beforehand? My team not only missed out on this learning but also those impromptu meetings or conversations that you have. The earwigging of someone’s conversation or a quick question as you go to get a coffee. All of this informal learning is lost when working remotely, and it is a massive challenge to capture and harness!

Richard FordRichard Ford


Richard is the co-founder of Hart Accounting Services. As an outsourced business, remote working is part of their DNA, and it’s a work culture that is always evolving.

“The single biggest challenge is probably helping our team to feel like they are still active, connected, and participating in day-to-day office life…”

The camaraderie that happens around coffee or lunchtime, or at the water cooler (to use the cliche), is something that’s very difficult to duplicate when team members are working remotely.

So, what we’ve done is we have a virtual coffee room, where team members dial in on Zoom or Teams, grab a coffee together, and catch up on work and life. One must be careful, though, to create the right hype and importance around connecting with colleagues—it shouldn’t feel mandatory or like it’s yet another meeting. It’s about the TEAM, and THEIR relationships and connections.

Dror ZaifmanDror Zaifman


Dror Zaifman is a Career Coach, a Finance Professional & a seasoned Director of Digital Marketing for iCASH. At iCASH, they aim to provide transparent, responsible, and fair-lending practices to help you reach your financial goals.

“Managing a remote workforce is very different from managing a workforce in the physical workplace…”

I believe effective communication is the biggest challenge we can face.

When working in a workplace, the environment is quite different and you have your entire team around you. You can readily communicate about any shortcoming and educate them about the changes required. You can also immediately see if they are motivated enough to work and make the required changes. However, this communication is not very effective when done over a video call, audio call, or in a group chat. It has much less impact, and you can’t tell how many of the team members are actively reacting to the instructions. Therefore, communication is still the biggest challenge of remote working.

John RussellJohn Russell


John Russell is a Partner & Founder at Russell & Co Chartered Accountants.

“The remote/hybrid model does have its issues, particularly when it comes to a new form of workplace equality it could bring with it…”

The vast majority of employees want to work from home, or at least engage in a hybrid model—but there’s already that feeling emerging of, ‘Should I head into the office?’ There’s an unspoken pressure there to be seen at your desk, to be engaged in the day-to-day office life. As the old saying goes, ‘Out of sight, out of mind,’ and I believe we’re going to see employees passed over for job promotions, bonuses, raises, or whatever it may be because they’re working from home and aren’t constantly present in the office. This will be particularly jarring for staff who are more productive at home than in the office, and it’s up to organizations to recognize all of their employees’ work rates and reward them based on merit, not based on where they are working from.

Shaunak AminShaunak Amin


Shaunak Amin is co-founder and CEO of STADIUM and SnackMagic. He is an experienced entrepreneur and operator and has helped launch and scale businesses in different industries.

“Many businesses now have hybrid employees spread across time zones…”

And many entrepreneurs believe team collaboration comes down to workers being available at all hours. However, this can put a significant amount of pressure on your team and lead to lower productivity and higher staff turnover. Fostering a good work/life balance for hybrid employees across time zones comes down to managers and each team member being mindful of their designated hours.

As projects require a significant amount of interaction, workers must be conscientious of when and how they contact their teammates to avoid burnout. Being considerate of time zones will help keep stress levels low and reduce the chances of human error. For this reason, outlining project tasks with realistic timelines from the onset is also essential to allow for a healthy work/life balance in remote work. Setting a clear direction and an even-keeled communication process will help keep your remote workers rowing in the same direction, increase their productivity, and give them time to enjoy their personal lives, too.

Michael AlexisMichael Alexis


Michael Alexis is the CEO of TeamBuilding.

“You need a way to provide the social aspect of work…”

One of the biggest challenges in managing a remote team is providing the social aspect of work. When employees come into an office, this social element is built-in—for example, saying hi in the morning or having lunch with colleagues. With remote work, you need to be much more intentional.

To remedy this difference, I recommend The 8% Rule. This rule states that you should spend 8% of the time in any remote meeting doing fun activities. For example, you might do a quick round of icebreaker questions, a game of online team building Bingo, a rapid-fire scavenger hunt, or similar. The rule is called 8% because it equals about five minutes for every hour spent on a call. For a 30 minute call you can adjust downward, for a 90-minute call adjust upward, and so on.

Farzad RashidiFarzad Rashidi


Farzad Rashidi is the Co-Founder of Respona.

“The single biggest challenge in managing a remote workforce is finding qualified employees…”

Finding qualified employees is one of the most difficult challenges in managing a remote workforce. This happens because it’s difficult to assess an employee fully without face-to-face contact or observing how they interact with other people. It’s also hard to know whether someone is being truthful on their resume, so reliability matters more too—especially when you’re hiring for customer-facing roles that are essential to your company’s success.

Teo VanyoTeo Vanyo

Teo Vanyo is the CEO of Stealth Agents, a virtual assistant service company that can significantly minimize overhead costs for business. They have a solid foundation, built on advanced technology and a highly trained workforce. Their number one priority is to provide all clients with incredible results.

“One big challenge when dealing with remote workforce management is the prioritization of tasks…”

Remote personnel must be self-motivated time management experts because they do not have people constantly overseeing their jobs or managing their time. While sticking to a schedule and managing to-dos is difficult for any employee, it’s especially difficult for remote workers who have more erratic schedules and managers spread around the globe. It’s hard to keep the pace of your work. Then there’s the constant temptation to watch one episode of your favorite show over your lunch break, clean up the kitchen while stalling on a job, or take your dog for a walk because they beg you to. Suddenly, you realize it’s night time, and you’ve accomplished nothing during the day.

Kyle MacDonaldKyle MacDonald


Kyle MacDonald is the Director of Operations at Force by Mojio.

“I think the single biggest challenge in managing a remote workforce is the initial transition…”

Transitioning your employees to do the same work in a remote environment needs a lot of planning and secure software, with a huge window for patience and empathy, too. Onboarding employees to use remote work practices, especially if they are new to the circumstances, is necessary but tedious work. Once you overcome the challenge of getting your employees to work confidently from home, you then have to face the challenge of maintaining camaraderie and a positive workplace culture from various locations. Through trial and error, you can absolutely provide good managerial practices for all of your employees.

Sanket ShahSanket Shah


Sanket Shah is one of the founders and the CEO at InVideo. InVideo is a SAAS business founded in 2017. They are a video creation platform that helps users transform content effortlessly into some amazing videos!

“Team communication is the biggest challenge when it comes to managing a remote workforce…”

Though many digital tools are out there for the team to stay connected, it still lacks the personalization of face-to-face conversations.

To work for the same goal and to stay motivated, your team needs to understand their roles and their mission, and for that, they need to communicate daily to stay on the same page. It is very hard to make everyone available at the same time because of different time zones. So many times there is a spontaneous meeting but a few members end up missing out due to various reasons.

So, keeping a proper flow of communication between the remote teams is very difficult.

Devon FataDevon Fata


Devon Fata is the CEO of Pixoul, a human-centric web design firm helping clients see better returns through intelligent, beautiful experiences.

“The hardest part of managing a remote workforce—really of managing any workforce—is effective communication…”

It’s essential for managers to not only communicate well with each of their employees but also to facilitate communication between employees who need to be collaborating. When done effectively, good communication with a remote workforce can be quicker and easier than in-office communication, but it takes some experimentation to get the right mix of all-staff communications, Zoom meetings, one-on-ones, and appointment-setting.

Daivat DholakiaDaivat Dholakia


Daivat Dholakia is the VP of Operations at Essenvia.

“The greatest challenge in managing a remote workforce is finding the balance between over and under-communicating…”

If you over-communicate, your team may feel like they are being micromanaged, and it can end up wasting a lot of their work time. If you under-communicate, your team may be confused about expectations and feel like they are not being led at all. Finding this balance may also change depending on the individual team members that you are leading because each person has different needs when it comes to working remotely.

Joe FlanaganJoe Flanagan


Joe Flanagan is the Senior Employment Advisor at VelvetJobs, the career matchmakers that connect 1M+ new curated jobs for jobseekers globally. He helps job candidates with all forms of career development and also helps businesses with their employer branding strategy.

“While collaboration is the first thing that comes to mind, one aspect that people often miss out on is visibility…”

Our traditional workplace, management practices, and business culture are built on managers being able to see, interact with, and question their team members. An almost disruptive shift to remote working has left a lot of managers—particularly the middle-tier management—in a lurch because their role was so closely intertwined with being physically present for their teams.

As a result, it has become more challenging to sustain the same cultural ethos or engagement practices of the physical workplace. While many businesses have tried to redefine the role of management and leadership, most leaders are struggling to comprehend their role beyond being in virtual meetings all the time. So, adapting the leadership, management, and production processes to match the remote work model has been the biggest challenge of the last year.

Liz Palmieri-CoonleyLiz Palmieri-Coonley


Liz Palmieri-Coonley is the Talent Optimization Consultant at MVP-Results.

“Even before the added challenges of COVID and managing remote teams, the most challenging part of a manager’s job is providing equitable leadership…”

It is a daunting task to understand and meet the needs of each team member. So listening to employees to gain understanding is vitally important. In a remote setting, managers must consider which mode of communication is best for engaging with individuals based on their preferences and the content.

Adam HempenstallAdam Hempenstall


Adam Hempenstall is the CEO and Founder of Better Proposals.

“Communication is the biggest issue with remote work and managing employees…”

We work a flexible schedule, which sometimes means waiting for hours until you get a reply from someone. However, we chose to go this path because it gives everyone more freedom in managing their workload and schedule. Especially if your employees work in different time zones, it’s really a challenge. The best way to get around this issue is to set aside a time block of 2-3 hours when everyone should be online to communicate with each other.

Sonu BubnaSonu Bubna


Originally a qualified accountant, Sonu co-founded Shopper.com, a global community of shopping enthusiasts with tens of thousands of active community members from over 40 countries. Sonu is passionate about women’s entrepreneurship and innovation.

“The single biggest challenge in managing a remote workforce is how to avoid burnout among staff…”

My team is composed of people from four different countries with different cultures. So, more than ever, this year has highlighted the importance of avoiding team burnout in remote working. As the lockdown progressed, I noticed a significant dip in the team performance due to burnout. Asking them to take enough breaks didn’t really help as most of them were new recruits and carried apprehensions.

Helping the team focus on what matters most is very important in avoiding burnout. In teams working remotely, they might miss the joy of working in a high-growth, tight-pressure environment as they did in a physical office. For instance, some people may miss making a collective decision or brainstorming sessions in the boardroom. Others may miss solving a problem by discussing it with a colleague. Hence, with a focus on what matters most, everyone has something to look forward to and a deadline to meet. Each day ends with a sense of accomplishment and people feel they are progressing.

Also, to reduce remote work burnout, we have ‘virtual coffee.’ Each team member is expected to speak to at least one other team member every day for 30 minutes. So, even if you have a hard day, you can talk to someone in a private environment irrespective of their role within the company. Having virtual coffees has helped my team to combat loneliness, keep mental health issues at bay and perform to their best ability in these unprecedented times of continuous remote work without burning out.

Jeff MeeksJeff Meeks

Jeff Meeks has 10 years of experience as a Product Manager and leader of cross-functional teams, including teams in organizations with revenue ranging from $5 million to over $5 billion. He has engaged with foreign and domestic customers, consumers, partners, and suppliers across several industries, including his current industry of consumer health fitness equipment with EnergyFit.

“Managing a remote workforce can be an exciting, yet difficult challenge…”

One of the biggest challenges can be maintaining open communication without behaving in a ‘watchdog’ manner over your employees. The ability to manage your workforce well, and keep productivity steady without being overbearing will allow your workforce to perform better and produce at an equal, if not better, rate than in-person.

Brandon HopkinsBrandon Hopkins


Brandon Hopkins is the founder of DiamondLinks, a results-focused SEO and online reputation management company. Brandon Hopkins has been a leader in the SEO industry for over 15 years. His experience as an SEO consultant spans many industries, including e-commerce, technology, education, finance, public figures, and many more.

“My company is based on remote workers, and I truly believe in the power of remote working…”

My goal is to have the most talented people work for my company, and that means those people may not be in my local city or even state.

However, remote working does pose unique challenges, like getting new employees trained in the best way possible. The training and onboarding period is a major factor in whether the employee will succeed with the company. They learn how the company operates, meet new people who will become friends, get a feel for expectations, and figure out how to work on their own every day.

This is much tougher when dealing with a remote employee and is a challenge for managers. I am still trying to find the perfect recipe to train remote employees so they are informed, motivated, and can be independent when they get to work.

CJ XiaCJ Xia


CJ Xia is the VP of Marketing & Sales at Boster Biological Technology.

“Some challenges that employers might face in having a remote workforce are…”

That they could be suspicious if their employees are actually working from home or indulging in house chores or family time. They tend to trust the employees less, and this creates a rift between the two, leading to a gap in communication.

They might also miss bossing over their employees, which they usually do in brick-and-mortar settings. Despite an employee putting his/her best in the job, suspicious employers might find productivity rates to be dipping.

On the other hand, there might be some employees who would genuinely take advantage of the situation and not work enough from the comfort of their home. Motivating them to get things done would be a huge challenge for employers.

Jared PobreJared Pobre


Jared Pobre and his wife Stacy Keibler are the Co-Founders of Caldera + Lab, a performance luxury skincare brand for men that harnesses pharmaceutical-grade science and nature’s purest, most potent ingredients. Jared’s personal wellness journey began when he met Stacy, who educated him on the importance of using non-toxic natural products and living a healthier, cleaner lifestyle.

“As the number of hybrid, remote, and in-house workers continues to increase, managers will begin to question how to measure the performance of their team members fairly and equitably…”

Many companies continue to use data to measure employee performance. But that may be a miscalculation as it’s merely a numeric description of their work. When it comes to the performance evaluation of hybrid-remote workers, empathy should be measured equally with data.

Considering your team member’s work history and the long-term relationships they have established with clients is vital. Everyone has their ups and downs at work—especially during times like these. So, looking at your employee’s overall performance and how it adds to your objectives is essential. Those long-term business relationships are built on empathy and trust. And the relationships you have with your employees should be, too.

Kate LipmanKate Lipman


Kate Lipman is a sales & marketing consultant for embrace Scar Therapy.

“A company’s culture is one of the main reasons why many people work at the companies that they do…”

Most people look at the culture of a company when deciding where to work, and many find that a positive work culture leads to more productivity. Due to this, it is immensely important to make sure that your remote workers feel connected and a part of your company culture. As a manager, you face the challenge of making sure your remote team has a feeling of togetherness, making them feel as if they were working next to you, not just a face on a screen.

Aiden ColeAiden Cole

Aiden Cole is the Co-Founder of HIDE. He is also the Co-Founder & CMO for Underlining and previously Head of Growth responsible for user growth, retention & monetization for dating apps acquired by Dating Group.

“The biggest challenge in managing a remote workforce is getting everyone on a consistent schedule…”

When employees are spread out throughout the country or even the world, scheduling can be difficult. For this reason, it’s best to keep remote workers on salaries rather than hourly pay.

Mike NemeroffMike Nemeroff


Mike Nemeroff is the CEO & Co-Founder at Rush Order Tee.

“The biggest challenge with regard to remote teams is engaging with a hybrid team…”

A business like ours that manufactures products will necessarily have on-site staff; not all jobs can be remote, but many of ours can. Historically there’s been little issue bridging the gap between office workers and production staff, but with the shift to remote, you have to get more creative.

With one team doing everything in a brand new way and the other largely unchanged at the core, it’s easy to get set up on two different pathways for work. Resolving issues and creating new workflows to accommodate these shifts in working styles is no easy matter, and any change in one side of your business necessarily affects the other, even if it’s less noticeable than before.

Amy BlockAmy Block


Amy Block is the Director of Marketing and Communications for Navitar, Inc. where she handles company and product branding, graphic and website design, advertising, corporate communications, and everything else marketing. Amy is a true professional, known by colleagues, friends, and family members as the “go-to-person.” She excels at research, creative problem solving, event planning, writing, and helping others navigate the digital world.

“Communication is one of the most important, yet difficult things to do well within a remote environment…”

With a loss of personal touch amidst direct messaging and video, as well as an increased ability to overschedule meetings, communicating in a proper form can at times come across as a real struggle. When figuring out how to best foster community within and communicate with your team remotely, ensure open discussion among employees as to what they are looking for, what works for them, and what would help them be more productive in the remote environment.

Malte ScholzMalte Scholz


Malte Scholz is a passionate product manager and technology enthusiast with deep knowledge in launching cross-platform SaaS and e-commerce products who co-founded Airfocus, a software solution that enables smarter roadmap prioritization for teams and solopreneurs.

“Communication seems to be one of the major challenges when it comes to managing a remote workforce…”

As a manager, you want people to stay connected and keep each other up to date with progress. However, too much online communication can easily become a distraction. Chatting is incredibly interesting and dynamic, so people may spend a lot of time talking about work-related or even random stuff. Your job is to identify when the boundary is crossed and correct people. This is perhaps the most unpleasant part because people can easily shut down and understand your feedback as a sign to drastically cut off communication.

Savvy organizations are leveraging data to drive management decisions and navigate the return to work while ensuring a positive employee experience. The Humanyze Platform helps organizations create data-driven, people-centric workplaces by uncovering the collaboration styles and workplace needs of teams, departments, and locations across the organization. Business leaders leverage this data to make the right decisions to support employee and organizational success.

Last Updated 11 November 2021