33 Remote Team Managers & Business Leaders Reveal the Most Significant Things That Keep Remote Team Managers Up at Night

Aternity March 18, 2021

In order to effectively manage any type of team, managers must promptly identify and address a range of workplace problems and issues. So it makes sense that these problems and issues are often compounded when it comes to managing remote teams in digital workplaces.

In fact, managing a remote team brings about a unique set of challenges for team managers, from productivity issues, to questions of how to facilitate collaboration, to managing the paradigm shift to remote work in general.

To learn more about the most pertinent problems and issues that play on the minds of remote team managers, we reached out to a panel of remote team managers and business leaders and asked them to answer this question:

“What’s the one thing that should be keeping remote team managers up at night?”


Meet Our Panel of Remote Team Managers & Business Leaders:

Keep reading to discover what our experts had to say about what should be keeping remote team managers up at night.

Olamide Olowe


Growing up with multiple chronic skin conditions, Olamide developed a passion for dermatology. As a student at UCLA, she co-founded SheaGIRL in partnership with Shea Moisture and discovered her love for business. Olamide Olowe is the co-founder and CEO of Topicals, a medicated skincare company for chronic skin conditions that is transforming the way people feel about skin by taking the focus off of perfect skin and celebrating the fun of flare-ups.

“It is so important to be checking in with your employees’ mental health during this time, which is why it should absolutely be keeping managers up at night…”

We are a company that puts a huge spotlight on mental health, so we do our best to not only translate that into our customer service, but also into how we interact with our employees. While they are all working remotely, we have done our best to do ‘check-ins’ often to make sure everyone is coping well and can handle their day-to-day responsibilities.

We have also made it a priority to celebrate our team’s successes often. Make sure, as a leader, that you are taking the steps to keep your employees feeling good and energized.

Carla Diaz


Carla Diaz is the co-founder of Broadband Search. Carla’s passion for data and technical chops led her to co-create Broadband Search. She believes the internet should be a human right and volunteers at her local animal shelter in her spare time.

“One thing that should be keeping remote team managers up at night is how to further streamline processes…”

If you’re running your remote team effectively, this area is where there is almost always room for improvement. It’s not a great thing to be kept up at night about problems because this means your team isn’t working how they should be. Rather, we should be kept up thinking about healthy alternatives to operations and the improvements that we can make to produce even better results in a shorter timeframe.

Claudia Cruz


Claudia Cruz serves as the link building manager for Thrive Agency.

“As a link building manager, what keeps me at night is whether our KPIs and goals are being met…”

You really have to believe and trust that your subordinates are hitting all those KPIs and goals! In the end, I just really have to set reasonable goals and have accountability—on both a daily and weekly basis as required, through such avenues as daily or weekly reports and meetings. I also have to analyze their progress, give and take timely feedback, and motivate the team.

Samuel David

Samuel David writes for Telewokin. Telewokin equips remote managers with the tools and tricks they need for successful hiring and onboarding.

“Finding what motivates each individual employee is one thing that should be keeping remote team managers up at night…”

Different things motivate different people. Autonomy, decision-making authority, career progression, and work-life balance are all examples of things that may drive people. Considering that motivated employees usually get the job done and are easier to manage, finding what motivates each employee is something that should be keeping remote team managers up at night.

Petra Odak


Petra Odak is a Chief Marketing Officer at Better Proposals, a simple yet incredibly powerful proposal software tool that helps you send high-converting, web-based business proposals in minutes. She’s a solution-oriented marketing enthusiast with more than 5 years of experience in various fields of marketing and project management.

“One thing that should be keeping remote team leaders up at night is solving the problem of micromanagement…”

If you constantly need to check whether someone did the job properly and whether they spend the full 8 hours in a day working, you probably hired the wrong kind of person or you have trust issues. If you hire the right people, you will be able to assign something to someone and let them submit the finished work without checking in every hour.

Micromanagement hurts your business in many ways, from wasting the time of both the managers and the employees, to losing great employees because of a poor company culture.

Stanley Tate

Stanley Tate is the owner and founder of Tate Law.

“Not having a clear communication policy should surely keep a remote team manager up at night both literally and figuratively…”

The biggest problem with remote work is effective collaboration. While using the right tools can curb this issue, it can lead to more confusion at times. You need to create a communication-process document to clearly illustrate when to use Slack, Gmail, Zoom, phone, etc.

There should be clear demarcation as to when to use a specific communication tool. For example, using Slack for quick internal messaging, Zoom for more important brainstorming sessions, and email solely for sending files and reports can be one way of doing it. This will ensure there is no miscommunication or confusion in terms of where a message was sent.

Bryan Philips


Bryan Philips is the Head of Marketing at In Motion Marketing.

“Remote team managers should only be kept up at night if they haven’t created a reliable system to vet, train, manage, and when necessary, fire their remote workers…”

Hire as if you were hiring for entrepreneurs. You want people as diligent and as conscientious as you are with your own work, especially when hiring remote workers. Those who do best with remote work are those who are actively engaged in their work. If your team needs babysitting, you should reinvent it with workers who don’t and stop losing sleep over it.

Sonu 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.

“In my opinion, the one thing that should keep remote team managers up at night is how to ensure team bonding in a virtual environment…”

My team is composed of people from four different countries with different cultures. So, more than ever, this year has highlighted the importance of team bonding in the virtual world. As the lockdown progressed, I noticed a significant dip in their team performance and interactions with each other. Asking them to talk often with each other was not really helping as most of them were new recruits, so they didn’t know each other and carried apprehensions.

Introducing the Rose & Thorn game allowed the team to open up and be vulnerable, creating an even stronger bond. As a result, we start the day with the Rose & Thorn game. In this game, each member gets one minute to talk about Rose (a positive that made them feel happy) and Thorn (a challenge they face). By playing this game in the virtual world, you can quickly encourage a humane feeling and bring your team together. In turn, you can increase the productivity and efficiency of your entire team.

John Cho

John Cho is the founder of My Pet Child.

“Remote managers should be kept up at night by concerns for their employees’ mental well-being…”

There are communication tools and apps for dealing with the business side of things when working remotely. However, your people are everything and will burn out if they take on too much. It can be harder to notice if you aren’t seeing the signs in person.

My Pet Child does a lot of hard work involving animal welfare, so I am constantly concerned that my employees are taking on more emotional labor than they can handle. So I try to check in as much as possible and cut some slack on certain things if people are showing signs of burnout.

Ishita Kaul

Ishita Kaul has been working in the IT sector for 3 years now. Apart from being tech-obsessed, she is creative at heart, too. She is the founder of Best Gift Ideas, where she lists and recommends gifts for every occasion and age group. She is an avid reader and takes interest in decor, as well.

“The one thing that I have learned about successfully managing a team and getting your team members to effectively complete their work is that…”

You need to communicate effectively with them and stand by them whenever they need your help. Collaboration is one of the aspects that has been seriously affected due to the COVID-19 pandemic. Though there are various types of software and virtual meeting platforms, team managers face a lot of issues getting their teams together to work on the same project at the same time. Be it the dividing of resources, working on the same thing simultaneously, or monitoring the progress of each member, collaboration tools aren’t that effective in giving you a real-time analysis of your project. So it is difficult to handle things together.

This is the thing that remote team managers should try to negate so that their team works smoothly. Regular meetings, using collaboration tools and integrating them with your company software, and having a feedback loop are a few methods through which you can improve collaboration among your team members and get jobs done faster. Collaboration is so very important since it increases productivity as well as team bonding so that no one feels left out when others are working on the project.

Sally Rong

Sally Rong established RELLERY, a crafted-in-the-USA jewelry brand, in 2018. While her plans and dreams for the brand have evolved, her ultimate goal has always remained the same—to craft meaningful, high-quality jewelry that is sold at a fair price.

“When it comes down to it, productivity is always the bottom line for remote teams…”

To be successful, all members of a team must work just as efficiently as they could from a singular office—and with just as much creativity and teamwork. To fill the gap that face-to-face meetings and impromptu discussions in the office can bring, remote managers must provide their teams with the tools that they need to succeed. Whether it be the latest team communication app or strategic marketing tools, these tools will keep everyone on the same page with the support that they require to feel properly engaged.

Omid Semino


Omid Semino is the owner of Diamond Mansion, a jeweler specializing in diamond engagement rings, wedding bands, and stud earrings.

“The question, ‘Am I being understanding and flexible enough to cater to my employees’ needs?’ should keep remote team leaders up at night…”

Flexibility is the most important aspect of keeping your team going through remote work days. There are plenty of challenges with working from home, and it is imperative that you are understanding of people’s time constraints.

You should absolutely be up at night wondering if you are doing enough to consistently work with your employees to come up with the best solutions to running your business remotely.

Muhammad Shabbar

Muhammad Shabbar is the HR and admin manager at Al Manal Development.

“Strategizing to hit your target is a reason to stay up at night…”

Having a well-thought-out plan to complete projects that will benefit everyone in your company is time well spent. Having said so, monitoring your remote employees, especially those who operate or work in a different time zone as you, is a must. Being present—even in a remote work environment—while implementing such strategies can boost employee morale. Doing so can also help managers to troubleshoot and address issues immediately.

Wayne Turmel


Wayne Turmel is the co-founder of the Remote Leadership Institute and author of 13 books including The Long-Distance Teammate- Stay Engaged and Connected While Working Anywhere. He lives in Las Vegas.

“If you have to only choose one, I’d pick the question, ‘How does your team communicate with each other when you’re not involved?’…”

Sure, you can have team meetings and see who participates and who doesn’t. You can pick up the vibe between team members if there’s a potential problem. But the real work of your virtual team happens when you’re not there (or it should!). How your team works together, communicates, solves conflict, and builds—and maintains—trust will be the determining factors in your team’s ultimate success.

Some of the things you should be watching for are:

  • Is everyone included in the work, or are cliques forming? Sometimes this can be the folks in the office working together more often at the expense of the remote team members. Or it might be the people with existing relationships excluding the newbies. As a leader, you might have to facilitate connections. A good way to do this is to assign people to work together who wouldn’t ordinarily self-select.
  • Are people participating in ways besides meetings? If you are using tools like Slack or Microsoft Teams, there are ongoing conversations about many topics. Some people proactively participate, providing answers, contributing to brainstorms, and asking the right questions. Others disappear from view.
  • Are you checking in with individuals about any challenges they’re having? Maybe you have picked up on some tension between teammates. For example, Bob is complaining a lot about Alice. In the office, you can pick up the vibe—the looks and body language that indicate tension or conflict. Online, all you hear is… silence. Don’t assume no news is good news. By the time it’s clear there’s a problem between team members, it may be much more difficult to resolve.

The stronger the connections between teammates, the more productive and engaged the team will be as a whole. When they work remotely, it’s easy (and natural) for folks to become siloed or not maintain the ties that made work in the office happen.

How they relate to each other when you’re not around may be the biggest indicator of the health of your remote team. And that should cause you to ask a lot of questions, even if it doesn’t really impact your sleep.

Teo Vanyo


Teo Vanyo is the founder and CEO of Stealth Agents. Since 2014, the company helps hundreds of businesses manage their operations, automate processes, and focus on what’s important. Stealth Agents provides jobs to 600+ team members in the Philippines and aims at helping people in third world countries overcome poverty.

“Thinking about managing company culture keeps me up at night…”

When people believe in your business values and have a shared vision, they stay connected, engaged, and make a great team (a team must have a shared vision to function). Once people lose connection to company culture, they stop believing in values and vision. So they start seeking work elsewhere.

Considering the resources we invest in recruiting, onboarding, and training new employees, retention is my number one priority. My company is built on its people. People drive my business forward, generating revenue, new customers, and opportunities. So I can’t afford to have a high turnover. And that’s why thinking about managing company culture keeps me up at night.

Jagoda Wieczorek


Jagoda Wieczorek is the HR manager at ResumeLab.

“Among the many things that have the power to keep remote managers up at night is having to fire someone…”

Regardless of how much managerial experience you have under your belt, letting someone go is never easy. It’s straight-up gut-wrenching if you’ve never done it before. After all, you’ll be introducing a major disturbance into a person’s life and likely bruise their feelings.

To somewhat soften the blow, break the bad news in person and stick to a firm, factual approach. Don’t torture them with small talk, but deliver the information within the first 30 seconds. When you lay the blow, touch upon why you decided to terminate the person with hard evidence like numbers, facts, examples of misconduct, etc. Next, offer resources to help. Unless you hate the person, assure them you’ll be happy to provide a robust reference letter and highlight their strengths on any reference check that will come later.

Deepak Shukla


Deepak Shukla is the founder and CEO of Pearl Lemon, a multi-award-winning SEO agency in London. Deepak bootstrapped the business from his mum’s house to the Pearl Lemon Group which did close to 650k USD in just its third year. He’s since gone on to invest in algorithmic trading, launch three apps, build a 5-figure online course, and start a plant-based food delivery service.

“What should keep remote managers awake at night is the possibility that collaboration/cooperation is being hindered by the disconnect inherent in a remote environment…”

Ever since I founded my SEO agency, Pearl Lemon, in 2016, my team and I have been completely remote. We are spread across multiple time zones and that, coupled with the differences in everyone’s individual schedules, proves to be a serious challenge. In these four years, I have found that the most daunting aspect is the disconnect that can arise between members of the team and figuring out what needs to be done to counteract it.

Akram Assaf


Akram Assaf is the co-founder of Bayt.com.

“I believe all remote team managers should be mindful of their own approach and self-belief…”

Some employees adapt better than others, but it’s your job to bridge that gap. Remote managers are and should be thinking about their managing skills and limiting self-beliefs. If this is keeping you up at night, your highest priority should be on resolving it.

Sean Nguyen

Sean Nguyen is the director of Internet Advisor.

“The thought of not being able to meet employees’ needs properly keeps me up at night…”

So does the thought that I’m not communicating effectively enough or that I’m not getting through to some of them.

Different employees have different needs, and being in a remote environment means that I’m not able to notice if someone is having a hard time.

I have to be constantly aware of it, constantly check on people, and make sure that I’m making time for each and every employee. That’s the kind of thing that should keep you up at night—not the thought that people are lazy at home, but the thought that you might not be as effective as you could be.

Cristian Stanciu

Cristian Stanciu is the owner and post-production coordinator of Veedyou Media, a company offering video editing services to videographers, marketing agencies, video production studios, and brands all over the globe.

“Back in the day when I started working with remote staff almost four years ago, my biggest concerns were about technical limitations…”

I would worry about things such as internet downtime and hardware, software, or computers not working properly. Basically, anything tech-related that could go wrong and would prevent me from communicating efficiently with my staff. As time passed, I realized that all those things were not actually happening that often in real life. The internet is pretty reliable and so are computers and most of the tools we use to create videos.

Fast forward to 2021. After managing a remote team at Veedyou since 2017, I can say without a shadow of a doubt that the biggest challenge for me is the working schedule.

That’s something that any remote team manager should keep in mind. When you work remotely, there is no 9 to 5. Team members like to choose their own hours. That’s the flexibility you get when you work remotely, and I don’t want to take away that from my staff. I have people on my team who prefer to work in the afternoon up to 10 or 11 PM, while others will work very early in the morning. I also manage video editors that are overseas. So when you throw in the time zone difference there, managing a remote team can become a 24/7 job.

If I want to communicate fast and efficiently with my staff, I need to be online when they are. That’s why the working hours are still something that keeps me up at night—literally.

Lately I’ve become a little bit better at dealing with this. One thing that has helped a lot is working from an office, instead of using my home office. This creates a bit of a separation between personal time and working time.

John Stevenson


John Stevenson is a marketing specialist for My GRE Exam Preparation.

“The one thing that should be keeping remote team managers up at night is reconsidering what productivity really means…”

Team managers should understand, especially during these changing times, that their team has a lot going on. Although this is not an excuse to not get work done, the pandemic has really caused us to approach work-life balance differently, so consider looking at areas where your remote team thrives.

If they struggle to perform in long-term projects, try breaking it down into smaller phases. If they’re having trouble taking advantage of their working hours, they might be more productive on a flexible schedule. It’s important to be a role model who emphasizes professionalism, but also flexibility and empowerment at the same time.

Liz Eddy


Liz Eddy is the co-founder of Lantern, an end-of-life planning service. Liz builds companies that tackle taboo topics. She founded her first social venture at age 15 that was focused on dating abuse and domestic violence education in schools. The organization has been running (on its own) for nearly half her life.

“The question that keeps me up at night is, ‘Am I being honest and transparent in my decision making?’…”

Oftentimes, people fear a situation will become worse if you admit to doing something wrong. In most cases, addressing your faults honestly and in a timely manner will only help improve the relationship you have with your employees and build trust.

Jing Gao


Jing Gao, the founder and CEO of Fly By Jing, is a chef, entrepreneur, and a renowned expert on Chinese cuisine on a mission to bring uncensored Chinese flavors to the table. She was the founder of an award-winning modern-Chinese fast casual restaurant in Shanghai.

“A question we are constantly asking ourselves as remote team managers is, ‘Are we still building and maintaining personal relationships with all of our employees?’…”

We love to have close connections with our workers, so the transition to remote work has been a challenge. To continue to nurture these relationships, we have found it’s all about balance. All remote team managers should be asking this question and coming up with solutions to maintain those relationships from home.

Allie Golon


Allie Golon joined IndustryMasters in 2016 as Vice President of Sales & Marketing. She currently serves as Managing Director where she is responsible for expanding market opportunities in North America. A former K-12 educator with an extensive sales, marketing, and project management background, Allie is the author of several books on learning style theory and brings an awareness of the power of experiential, hands-on learning to her work in the design of simulations.

“We believe the one thing that should be keeping remote team managers up at night is maintaining leadership development and training opportunities among their team…”

Now that nearly everyone has gone to a remote-based office structure, how will managers keep their teams engaged, motivated, and growing in their roles while preparing to advance to higher levels?

While the ways in which teams collaborate changed dramatically in 2020, there’s no need for individuals to feel stagnated in their positions. Significant training experiences that focus on improving business acumen skills, enhancing decision-making ability, and more are available for online, remote-based participation, and do not compromise learning objectives.

Mark Hayes


Mark Hayes is the Head of Marketing at Kintell.

“‘Do my employees feel heard?’ is one question that keeps remote team managers up at night…”

It’s difficult to ascertain how well your employees are coping with their responsibilities while working remotely. In an office environment, you can easily observe who is struggling and who is not. In the comfort of your own home, however, you need to take further action. To ensure that your employees feel heard, it’s important to reach out to them individually. It’s important to check in and see whether the employee in question would like to discuss a problem privately.

It’s better not to ask this question in a group chat environment. People are often less inclined to respond in public due to the ‘group mentality’ that somebody else will. Instead, send a personalized private message. By private messaging, it demonstrates that the recipient is valued not just as an employee, but also as a person. To make your team feel heard, show that you’re listening.

Kris Kelso


Kris Kelso is an executive coach, leadership advisor, and keynote speaker based in Nashville, TN. He is also the author of Overcoming The Impostor: Silence Your Inner Critic and Lead with Confidence.

“Given that isolation can feed impostor syndrome, one thing that keeps remote team managers up at night is how their employees are feeling…”

When your team members are disconnected, the voice of their inner critic can become louder than the voices of encouragement and support they would get from being more connected with their peers and leaders. Even worse, the fear that they’ll be shamed or punished for their insecurity will keep them from reaching out and asking for help.

Managers of remote workers therefore need to be even more proactive in encouraging their team members and helping them battle their inner critics.

Adam Wood


Adam Wood is the co-founder of RevenueGeeks and an FBA enthusiast. RevenueGeeks’ mission is to research and review online selling tools with the main focus being Amazon, the largest online marketplace in the world.

“A manager shouldn’t sleep until they find the right workflow for their team…”

 The right workflow saves time, money, and resources that every company needs for growing and expanding.

I lost some sleep and my dream schedule got messed up because our workflow was very new when we were expanding. This is critical in the early days because every cent you lose hurts much more now than it does later on. A messy workflow means that you are losing money, and that can’t happen at any step in a company. Every moment invested in this step is crucial for the growth of a company, that’s why you should lose sleep here.

Matt Erhard


Matt Erhard is a managing partner at Summit Search Group. He has over 10 years of experience in leadership and strategic management and has partnered with global, national, and non-profit organizations across a wide range of industries, providing strategic direction on human capital. Matt’s area of focus has been in identifying and recruiting top-notch performers in sales, marketing, operations and management, non-profit, and executive search.

“Cliques weren’t a significant concern in the workplace before our shift to remote work, but I am noticing them becoming an issue…”

The main source is the divide between employees who have been with us since before 2020 and those hired and onboarded virtually during the pandemic. This hasn’t yet impacted anyone’s ability to work and collaborate. However, it’s obvious from conversations during meetings and on team message boards that coworkers who were friends before have continued their social interactions, and the newcomers to the team aren’t being included.

Granted, I know this isn’t all due to remote work. It always takes some time to settle into a new workplace, and some of these employees have only been with us for a few months. I’m also paying closer attention to how the team socializes than I normally would—I’m not sure how long it usually takes a new employee to start socializing with the team because that’s not something I’ve ever tracked before. That said, I’m keeping my eye on the situation and thinking of ways I can open up more opportunities for new team members to feel included.

Tom Winter


Tom Winter is an inveterate hacker, whether it comes to automating the tech recruitment process or enhancing his morning commute with an electric skateboard. At work, he is the lead tech recruitment advisor and co-founder of DevSkiller, a developer screening and online interview platform powered by RealLifeTesting™.

“The psychological impact of transitioning to remote work and trying to figure out if all the employees are happy with the transition is the most significant thing that keeps remote team managers up at night…”

Some employees absolutely love working remotely, whereas others struggle to adjust and need more help. Now that remote work is the standard, managers need to find ways to make sure every employee is satisfied with the new work model.

So it’s crucial to give extra attention to those that are having issues with the remote transition, as it can end up affecting them psychologically, resulting in poor work performance in the long term. As a remote team manager, the well-being of my employees definitely keeps me up at night, especially this past year!

Amir Yazdan, M.D.


Amir Yazdan, M.D. is a board-certified physician and hair restoration surgeon. Amir dedicated his life to solving male pattern baldness and female pattern hair loss through his practice as a world-renowned hair restoration surgeon. He is also the founder of GroMD, a company offering products that are effective and easy-to-use, so everyone can adopt a simple daily regimen that prevents hair loss—no desperate measures required.

“Remote managers certainly have a lot on their minds, especially if their work-from-home team has grown during the pandemic…”

Whether you’re managing a group of freelancers or you have moved your team to remote work for their safety during the pandemic, the struggles are still the same. And the one issue that can cause many sleepless nights is when the time comes to hire additional remote workers.

While the hiring process is basically the same, except replacing an in-person interview with a convenient Zoom or Skype call, the main distinction comes in when targeting the types of employees to hire.

In fact, when hiring remote workers, what you should actually be looking for is entrepreneurs. Those potential candidates who exhibit an entrepreneurial mindset will provide several advantages over a team member who is simply ready to be an employee. Look for potential team members who are innovative, seem ready to think outside of the box, and will be able to work with little to no supervision.

Rex Freiberger


Rex Freiberger is the CEO of The Call Of, a top travel and lifestyle guide dedicated to helping you connect with other cultures and your inner self.

“One of the things I worry about is how much my employees are working…”

I know many managers fear their employees are slacking off when they’re working remotely, but I feel very strongly that this is rarely the case. If anything, people tend to work more when there are no clear boundaries between work and home. This has been the case for my team.

I’ve had to remind them to step away at 5 PM or not answer emails on weekends. I can’t hover and keep them from doing it all the time, however, and so there are a lot of cases where people are putting in more hours than they’re being paid for.

To me, this is unacceptable. Aside from being unhealthy for work/life balance, it’s far more likely to burn employees out and drastically reduce their productivity.

Ben Taylor


Ben Taylor is the founder of HomeWorkingClub, an advice portal for remote workers.

“There are many things remote managers can worry about, but one thing they should particularly worry about is where all the data is…”

File management can become very chaotic in a remote environment, and it’s not solely down to the IT team to worry about it. Much of the time, where important data ends up is the result of workflow and process.

Staff must have clear guidelines on how to store files and manage data. Company information shouldn’t be spread around in numerous different systems and on the desktops of people’s home computers.

Chris Bolz


Chris Bolz is the CEO of Retail CRM Cloud, a SaaS software specifically made for retailers.

“Employee work-life balance is the most significant thing that keeps remote team managers up at night…”

While working remotely has its numerous benefits, many companies noticed the borders between personal and professional life getting blurry as we go into a more digitized chapter of life and work.

So if you manage a remote team and are up at night thinking about issues, this illustrates the problem of balance perfectly.