7 Challenges to Overcome When Managing Remote Workers

As remote teams of professionals become the norm, managers are embracing the benefits they provide.

According to Upwork’s Future Workforce Pulse Report from 2020, hiring managers at the time saw an early uptick in productivity due to remote work—a trend that has continued as teams have adapted and technologies have improved. And, because of the effectiveness of remote work and its benefits, about 92 million workers are expected to go fully remote by 2030, says the World Economic Forum.

But if shifting to a distributed workforce can yield clear advantages, doing so also raises new management challenges.

Every company will have unique issues and solutions best suited to the particular needs of its remote team members. But a few challenges consistently arise across many kinds of organizations with remote workers.

Thankfully, these obstacles can be overcome with simple yet effective management strategies. This article details seven of the biggest challenges faced when managing a remote team by type. Issues include communication, productivity and accountability, and engagement and culture. Each one is paired with tips for how to surmount it successfully.

Communication challenges

Misunderstandings and a lack of team cohesion happen more frequently when messages are typed instead of spoken. Without face-to-face interaction, tone can be misread, and details missed. Managing this starts with selecting the right communication tools, defining effective communication channels, and setting clear expectations.

1. Coordinating schedules

Building a remote workforce can significantly expand your access to talent, allowing you to engage with professionals throughout the country and across the world. But when you recruit the top professionals from a global talent pool, there’s a good chance they’ll live in different time zones.

Sometimes, this can be a good thing. When workers are in different time zones, they can stagger their efforts and work more effectively. For example, customer service teams can provide round-the-clock support when professionals have sequential hours based on their locations. As team members finish for the workday, they can hand off open items to colleagues in another city or country who are just starting theirs.

But conducting meetings, training, and other collective activities can be a challenge for a global workforce. You can’t expect professionals to attend meetings regularly in the wee hours of the morning just because that time slot works for you. Even spontaneous interactions can be difficult: If it’s late at night in another team member’s time zone, you can’t ping them with a “quick question” and expect a quick response.

With many companies committing to fully or partially remote workforces moving forward, it’s essential for teams to learn how to work cohesively, even when physically apart.

Solutions for coordinating remote team schedules

Coordinating remote team schedules across time zones can be a challenge, but with the right systems in place, your team can stay aligned and productive.

• Create helpful resources and update them regularly. When managing a global team, you don’t want workers dependent on you for brief, simple instructions. If something comes up while you’re not online, they could be stuck until you reply. Invest time in making rich and comprehensive resource hubs where workers can find direction for common questions and challenges. Keep these shared resources constantly updated in real time so guidance is never erroneous or obsolete.
• Utilize collaboration tools. As remote work has become standard across industries, novel collaboration platforms have emerged to serve distributed teams. These tools take several shapes and perform many functions, from task management apps to communication channels. For example, when differing schedules come into play, a shared project management tool or platform can be a lifesaver. By recording progress, challenges, and instructions in a central location, these apps make it easy for team members to work together across different time zones.
• Record and share certain virtual meetings. If a worker can’t make a meeting, record it for them to view later. Because remote meetings occur by phone or video conference, you should be able to record them easily. If you take this approach, invite team members who can’t attend live to submit questions and comments ahead of time. That way, you can address their thoughts in the meeting and allow other attendees to consider their input.

If you’re working with independent professionals, clarity around time zones and availability becomes even more important. Freelancers often manage multiple clients, so coordinating deadlines and communication expectations upfront helps avoid delays. Shared calendars, clear meeting schedules, and asynchronous-friendly tools make collaboration smoother for both freelance and full-time team members.

2. Communicating consistently

Communication can make or break any team. For distributed workforces, however, the manner, frequency, and style of your communication can be especially important.  

Many challenges relate to the virtual tools that remote teams use. Emails can be missed or misread. Chat messaging can arrive at busy moments, only to be forgotten as the day goes on. Miscommunication arises in traditional office settings, too, but remote teams’ reliance on these tools considerably increases the likelihood of it happening and the stakes when it does.

Additionally, when interactions occur on these digital platforms, important contextual cues can be lost or missing altogether. A written message creates ample opportunity for misinterpretation, especially about its sender’s tone and intentions. In the context of a global team, cultural differences and language barriers can also create confusion.

Independent talent may also not have the same line of sight into the business as full-time employees. So you may need to make extra effort to ensure they understand how their work affects the company or departmental goals, how they contribute to the bottom line, and why they’ve been assigned specific tasks.

These issues are hardly insurmountable. With a few thoughtful adjustments, you can implement solid remote communication practices across your distributed team.

Best practices for communicating with remote workers

Strong communication is the foundation of a successful remote team—especially when team members span locations, time zones, and working styles.

• Err on the side of empathy. Be careful with your tone in emails and messages to combat the risk of digital miscommunication. Stay friendly, relatable, and positive. Although everyone is busy, there is always time to make a message more human with a simple greeting or acknowledgment. That doesn’t mean you can’t be assertive, but try to stay courteous even in uncomfortable conversations.
• Meet individually often. In contrast to larger groups, one-on-one video meetings offer exceptional opportunities for transparent communication and feedback. There’s no better way to ensure you’re on the same page or address a worker’s concerns. And don’t just schedule them when something goes wrong; make them a regular part of your approach.
• Choose a communication hub. Managing remote collaboration requires a centralized spot where general updates and interpersonal communication can happen asynchronously. While other communication tools are important complements (email and chat, for example), maintaining a primary platform keeps everyone updated and accountable. Plus, remote team members with different schedules can all keep an eye on progress or get up to speed quickly.
• Set clear expectations for communication. Don’t leave your team guessing how they should communicate with you and other colleagues. When they join your team, clearly specify communication expectations, including how, when, and whom to update and which tools to use. With mutual expectations around sharing information, everyone can play their role with additional confidence.

When integrating freelancers into your team, don’t assume they’ll pick up on company norms automatically. Be sure to onboard them with the same communication tools and standards you use internally. Creating a brief guide on communication channels, tone, and response expectations can go a long way toward preventing miscommunication.

3. Conducting effective team meetings

Getting the entire remote team together for a meeting can be challenging when everyone’s on different schedules. You’ll want to make sure meetings are as productive as possible when you’re able to gather the full group.

When your team does have meetings, make sure to follow an agenda. Agendas keep meetings focused on what’s most important. Additionally, they allow team members to prepare questions beforehand, as they’ll know the goal of the meeting before it starts.

Solutions for better remote team meetings

Remote meetings are most effective when they’re intentional, well-equipped, and structured to support meaningful participation from all attendees.

• Plan a meeting agenda. Coordinating a remote meeting takes effort, so ensure you cover all the necessary items. Creating an agenda ensures you don’t waste time and that attendees know what to do as prerequisite and what to expect in the meeting. By sharing the agenda and expectations beforehand,team members can prepare and be more likely to participate.
• Use the right tools. Productive meetings can be essential to completing a project and matching client expectations. However, not all teams will need the same tools. For example, some teams might need access to file-sharing services, while others might require scheduling services like Google Calendar.  
• Ensure workers have quality equipment. If you expect great work results, it’s important to ensure full-time workers have the right equipment. For remote workers to be productive, they’ll need reliable equipment that won’t delay them in attending and participating in meetings. If your team includes independent professionals, though, they’ll typically have their own tools and software. Just make sure it’s compatible with whatever your team is using.

If your project involves freelancers, consider whether they should attend virtual meetings or receive highlights asynchronously. Freelancers often operate independently, but regular check-ins or periodic invites to broader team calls can help build trust and keep everyone aligned.

Productivity and accountability challenges

Remote work allows for autonomy, but also requires new ways of tracking progress, setting work hours, and providing feedback. Too much oversight can stifle performance, while too little creates gaps.

4. Balancing trust and accountability

For some managers, remote work raises fears concerning accountability and productivity. If professionals are at home rather than in the office, will they succumb to distraction and slack off?

Our research suggests these worries are unfounded. Hiring managers have noticed an increase in productivity, attributed to a reduction in non-essential meetings, a flexible work schedule, and a lack of commute.

However, just as you would with an in-office team, you’ll need to find the balance between effective oversight and smothering scrutiny.

Don’t fall into the trap of micromanagement: If you’re constantly checking in without a real reason to do so, you’ll impede productivity overall. Strong workers thrive with additional autonomy, whereas you risk stifling them with pesky intrusions.

On the other hand, you should provide the information and expectations necessary for your team to execute effectively and be available when needs for your help arise.

Suggested solutions for balancing trust and accountability with remote workers

Balancing autonomy with clear expectations helps remote teams stay productive while building mutual trust and long-term working relationships.

• Define deadlines and deliverables clearly. Be extremely clear about what you expect team members to accomplish and the time frame they have to deliver. This stage is crucial, and a little extra effort up front can prevent a ton of frustration later. That being said, delays and setbacks do happen and should be addressed transparently. Set up a standardized process for professionals to ask for extensions or request additional help if they fall behind.
• Communicate overall project goals. Because remote team members are often accountable for just one component of a greater effort, the big picture can sometimes seem unclear. In meetings and other forms of communication, consider outlining your larger goals to the entire team, and do so consistently as you proceed. When professionals see their work within this collective effort, they’ll be motivated to perform well to support other team members and they may have insights that will benefit the overall project.
• Compensate correctly. Nothing drains morale, loyalty, and energy from a remote team, like late, missing, or incomplete payments. Payment details outside a traditional weekly paycheck can sometimes be tricky, but if independent talent make up part of your remote team, and you agree to pay at a certain rate or based on a project, hold up your end of the bargain.

5. Coordinating tasks and projects

Managing different schedules, time zones, and workloads adds another layer of difficulty in coordinating tasks and projects. Ensuring all client needs are met can be challenging to achieve unless you’ve developed a system for coordinating projects.

By coordinating who’s in charge of what aspect of the project, every team member understands their role in achieving the common goal. And project managers play a key role in this. Need an experienced project manager to lead your remote project? Upwork can help you find the best independent project managers for your project.  

Without coordination, resources are wasted, and results are sometimes delayed. 

Solutions for coordinating tasks between remote workers

Coordinating remote work requires early alignment, consistent communication, and clear project visibility for every contributor.

• Ensure team members are involved from the start. Having to explain the goals and scope halfway through the project can inhibit productivity. For this reason, all team members should be included in the project from the start, as adding a person halfway through the project can slow everyone down. Any changes in strategy or tactics should also be shared promptly.
• Start the project with a meeting. Even if your distributed team is in different time zones, it’s important to set a meeting in which everyone is included to kick off the project. During this meeting, the team should define and agree on the project goal, scope, and timeline.
• Stay in communication. Maintain communications with your team to discuss the project and offer support when needed. Although instant messaging is helpful to keep in touch about project progress, using video conferencing tools like Google Meet or Zoom can help cut through any confusion. In addition, hopping on quick calls to clarify specific tasks or answer questions can often cut back on the time you would have spent typing a detailed explanation in a chat or email. ‍

6. Managing productivity

Since the early shift to remote work, concerns about lost productivity have faded. In recent years, surveys have shown that the majority of hiring managers now report smoother workflows and improved outcomes with distributed teams, thanks to clearer communication strategies, better collaboration tools, and more refined remote processes.

As a remote team manager, keeping track of project deadlines and how workers handle their work can be challenging. You don’t want to come across as a micromanager, but you also want to be approachable and offer support to workers. To help avoid this issue, schedule regular check-ins. This way, the remote worker can provide an update on their progress or explain where they’re struggling in any way. All in all, when a team is built on a foundation of trust and team members have the space to express themselves, they can do their jobs more effectively.

Solutions for improved productivity of remote workers

Here are additional ways to streamline productivity:

• Ensure workers know they’re valued. When team members know they’re important to others on their team, they’re more likely to be engaged and motivated. Congratulating workers for accomplishments, providing rewards when you can see they’ve been working hard, and celebrating birthdays, milestones, and special events can help team members feel supported and important.
• Create a positive environment. While many companies have invested in creating a welcoming office, the remote environment can lack the excitement of going into a “fun” office. Encouraging workers to create a place to work, away from distractions, can help them deliver work on time. Another way to improve their environment is by providing additional tools. Consider offering full-time remote employees a second monitor or a standing desk.
• Choose key performance indicators (KPIs) and metrics to track performance. KPIs allow teams to measure their progress toward a goal. All teams can benefit from setting KPIs, but it’s especially important for remote teams, as managers can’t physically see workers working. For example, if a remote worker is struggling, their manager might only see that they aren’t delivering work, not that they’re having trouble reaching goals. Keeping up to date on everyone’s progress ensures you can act fast to stay on track.

When working with independent professionals, use clearly defined deliverables and outcome-based KPIs rather than tracking hours. Most freelancers prefer results-oriented oversight, and this method helps you evaluate outcomes without micromanaging their day-to-day workflow.

Engagement and culture challenges

Without casual chats or onsite celebrations, some remote employees feel disconnected due to a lack of social interaction. Building a strong sense of belonging requires intention: thoughtful team-building activities, personalized check-ins, and ongoing reinforcement of your company’s values.

Recognizing which category a problem falls into can help you solve it more effectively and avoid burnout across your remote team.

7. Creating connection

Leading a distributed workforce demands adapting traditional approaches to cultivating a strong company culture. For example, in-person perks and events may not be accessible to all team members, if they’re feasible at all. Likewise, building camaraderie isn’t as simple as gathering in the break room for Monday morning bagels.

However, creating and maintaining a warm and positive collective vibe among team members is crucial to remote work’s success. While remote work entails a ton of benefits, it can sometimes feel isolating. Because remote professionals don’t have face-to-face interactions, you’ll need to intentionally cultivate a sense of inclusion and collaboration.

The need for community extends to independent professionals, whom businesses are increasingly engaging to work alongside full-time employees. If you lead a “hybrid team” made up of independent talent and full-time employees, consider how to support the entire team, not just employees.

Fortunately, with the right management support, remote teams can foster strong working relationships. 

Solutions for creating connection within a remote team

Building strong team bonds in a remote setting takes intentional effort, consistent recognition, and opportunities for authentic interaction.

• Celebrate success. Whether you give shoutouts during weekly Zoom happy hours or do virtual high-fives throughout the week on Slack, highlighting success in creative and public ways can help connect team members. Sharing the high points of everyone’s workweek makes workers feel seen, included, and appreciated, which translates to a greater desire to perform well for the company.
• Make time to meet. Remote teams can drift toward impersonal communication methods or even feelings of isolation. When a question or issue comes up, it’s easy to send an email or chat message. However, take the time to recognize when a meeting might be better. By using video conferencing, particularly within teams working toward a shared goal, you can enrich professional relationships in important ways. The video piece is important: There’s something undeniably personal about making eye contact.
• Keep the announcements and updates coming. Nothing erodes culture like confusion about the company’s direction. Providing regular updates on everybody’s progress, company goals, and other important group announcements can unify team members through a shared sense of purpose.

Remote work trends and talent strategy

Remote teams work best when everyone has a clear role, but sometimes, internal capacity falls short. Whether you're missing a project lead, data analyst, or customer support specialist, freelancers can help fill those gaps without overburdening your full-time and remote workforce.

Engaging independent professionals allows you to scale quickly and flexibly. Many have experience jumping into remote team environments, working across different time zones, and using popular communication and project management tools.

Here’s how freelancers can strengthen your remote team:

• Fill specialized skill gaps. Whether it’s content, design, or engineering, freelancers bring niche expertise without long-term commitments.
• Handle overflow or short-term needs. Bring in support during busy cycles, product launches, or seasonal spikes.
• Keep the core team focused. Freelancers can own entire workflows, allowing your full-time team to focus on strategy and high-priority tasks.

Now, with millions of professionals working from home, businesses need to shift their remote team management approach from reactive to strategic. Hiring managers must rethink everything from onboarding and workflows to measuring outcomes and maintaining mental health.

Successful teams invest in:

• Strong communication infrastructure. Tools like Trello, Asana, Slack, and Zoom help maintain visibility and connection across teams.
• Clear role design. Well-defined expectations reduce overlap and build trust.
• Flexible work policies. Offering flexibility around work hours and workspace helps promote well-being, a solid work-life balance, and retention.

Companies that master remote work strategy—and tap into global freelance talent—can compete for top-tier professionals without being limited by geography.

Build a stronger remote team with Upwork

Managing remote teams takes more than just video calls and productivity tools—it takes intention, trust, and the right team composition. The challenges of managing remote employees may be real, but they’re manageable with thoughtful planning and clear communication.

Whether you’re dealing with time zone conflicts, miscommunication, or low employee engagement, the strategies in this guide can help create a more resilient, effective remote work environment. And with access to global talent, including top-tier freelancers, you can flexibly fill roles, cover skills gaps, and strengthen your entire team.

If you want to augment your current workforce with top independent talent, Upwork is the platform for you. We make it surprisingly quick and simple to engage professionals worldwide with the exact skill sets you need. When you add the right talent to your remote team, you’ll find leading it a lot less challenging. Plus, our tools make it easier to engage and work with independent talent, from communicating project parameters to establishing payment details.