Remote work wasn’t new when the pandemic hit—it had been quietly growing for years. But when COVID-19 forced millions out of offices overnight, everything changed. Companies that had spent decades refining in-office operations suddenly had to rethink how to lead, collaborate and stay connected without physical proximity. For some, the shift was seamless. For others, it was like learning to swim by being thrown into the deep end.
“Transitioning from in-person to remote is far more challenging than building a remote-first company from scratch,” says Spencer Badanai, head of customer services at Citizenship Italia, an Italian law firm specializing in securing dual Italian citizenship for people with Italian heritage. “Some employees will adapt, but for many, it just won’t be the right fit—not because they aren’t great, but because it’s not what they signed up for.”
Even for companies that fully embraced remote work, leadership in a virtual setting is different. “Remote leaders must hone their communication skills to a higher level than office-based counterparts,” says Jen Phillips, a remote operations leader who has led teams across regions, time zones and job types. “We have to work harder to create ‘real moments’ in every meeting, virtual coffee break and one-on-one.”
So how do you lead when there are no hallway conversations or impromptu desk-side chats? How do you build trust, spot burnout and make people feel valued when you may never meet them in person? For leaders, the remote revolution isn’t just about adapting; it’s about reimagining what leadership looks like in a world where connection happens through screens.
Here are five real-world problems in virtual companies and ways to address them.
1. Problem: Communication breakdown
A single misplaced period in an email. A Slack message that lands wrong. A meeting that should have been an email — but wasn’t.
Remote teams rely on written communication more than in-person teams, but without body language or tone, misinterpretations are inevitable. A simple update can spark anxiety: Why did they phrase it like that? Am I missing something? Without the quick clarifications of in-person work, minor misunderstandings can snowball into frustration and lost productivity.
Solution: Fewer meetings, clear expectations
The instinctive fix for miscommunication? More meetings. The real fix? Fewer — but better — ones.
“Remote meetings are where productivity goes to die,” says Peter Murphy Lewis, an expert at managing distributed teams. “If it can be solved in Slack, we don’t need a meeting.”
Instead of pulling people into endless syncs, Lewis’s team relies on Loom videos for status updates and Notion templates for project kickoffs, where people contribute their thoughts asynchronously. These actions have cut meeting time by 40% and improved response times, he says.
Phillips agrees that structured, intentional communication is key. “If you don’t define how a team will communicate — on which channels, in what time windows — you accelerate burnout,” she says. Instead of a free-for-all, she suggests that strong remote teams establish clear norms — when to use Slack versus email, when asynchronous updates work best and when a meeting is actually necessary.
2. Problem: Measuring performance without micromanaging
In an office, productivity is easy to observe — employees are at their desks, working late, speaking up in meetings. But in a remote setting, where work happens in home offices and coffee shops, leaders often feel like they’ve lost visibility. For some, that’s unsettling. Without physical proof that work is happening, many default to constant check-ins, excessive meetings and an unspoken expectation to always be online.
“It’s important for leaders to keep in mind that trust is a two-way street,” says Andrew Brodsky, a management professor at the University of Texas at Austin and author of Ping: The Secrets of Successful Virtual Communication. When employees feel monitored rather than empowered, they disengage. Rather than taking ownership, they wait for approval, leading to slower execution and lower engagement.
Solution: Trust your team
The real challenge of remote leadership isn’t productivity; it’s trust. Most leaders were trained in an office culture where presence equaled performance. But without the ability to physically “see” work happening, great leaders must shift their focus from presence to predictability.
The key shift? Define clear success metrics — whether that’s weekly deliverables, project milestones or client outcomes — and use those to measure performance instead of time spent online.
“Can your team consistently deliver without needing you to check in?” Lewis asks. “If not, the issue isn’t remote work. It’s that expectations, processes or trust are broken.” Instead of relying on constant supervision, Lewis advocates for empowering decision-making. “Have your team write down every decision they made within a week and categorize them: leader-led or team-led?” Lewis explains. “If every decision goes through you, you’re the bottleneck. Your team isn’t failing — you just haven’t given them the authority to execute.”
3. Problem: Recognizing burnout
Burnout doesn’t always announce itself. There are no slumped shoulders, no long sighs at the desk, no visible exhaustion. In a remote setting, the signs are quieter: a shift in tone on Slack, fewer contributions in meetings, a once-diligent employee starting to miss deadlines. Without in-person cues, many leaders don’t notice burnout until it’s too late.
Brodsky calls it the autonomy paradox, the illusion that remote work gives employees more freedom, when in reality, it can make them feel like they have to be always on. “More control over when and where we work should reduce stress, but it often does the opposite. When employees have no clear boundaries, they feel a stronger need to stay constantly plugged in,” he says.
Solution: Set — and enforce — boundaries
The best leaders don’t just encourage employees to set boundaries. They actively protect them. If the company culture values responsiveness over well-being, employees will hesitate to log off, take breaks or say no to extra work. That’s why leaders must model the behavior they want to see, whether that’s disconnecting after hours, taking real vacations or reinforcing that no one should feel guilty for stepping away.
And when burnout does creep in? Talk about it. Phillips advises leaders to check in with employees using simple but direct questions:
• How is your energy? (Are you feeling drained?)
• How is your mindset? (Are you becoming cynical about your work?)
• How effective do you feel? (Are you struggling to do your job well?)
The answers to these questions can reveal burnout before it escalates. Because in a remote setting, recognizing burnout isn’t just about watching for signs. It’s about listening before it’s too late.
4. Problem: Building a collaborative culture
For remote teams, culture isn’t a break room stocked with snacks or after-work drinks. It’s something less tangible but more powerful: a sense of belonging. And without it, teams become transactional: Colleagues communicate when necessary but rarely collaborate beyond what’s required.
“Most remote leaders have zero idea how to create culture,” Lewis says. “They believe that it consists of Zoom happy hours and forced fun. It doesn’t. Nobody wants to have a virtual trivia night. Nobody wants to answer icebreaker questions. Culture is not a forced event; it is the daily action you allow (or don’t).”
Solution: Encourage ownership
At Lewis’s company, culture isn’t something scheduled — it’s something built into the way people work. Every employee writes their own job description, reinforcing a sense of ownership from day one. This process forces employees to think beyond their own tasks and consider how their work connects with others. When employees take ownership of their roles, they also take responsibility for how their contributions impact the team.
Ownership creates accountability, but it also breaks down silos. Employees don’t just do their jobs; they shape how they collaborate, improve processes and support teammates. Instead of waiting for top-down direction, teams naturally align, challenge each other and refine workflows together.
“If they know their role better than I do, they own it. That’s how you build culture — by creating an environment where people challenge and support each other.”
Remote culture isn’t about planning bonding activities. It’s about how people interact when no one is watching, how teams support each other without being asked and how work itself fosters connection, not just completion.
5. Problem: Supporting career advancement
For ambitious employees, career growth isn’t just about doing great work. It’s about making sure that work is seen. In an office, that visibility happens naturally. A manager walks by and notices you handling a tough client call. A casual lunch sparks a conversation about your next career move. Remote workers don’t get those moments of serendipity. Without face-to-face interactions, career progression can feel less like a ladder and more like a maze — one where only the most visible find their way forward.
Solution: Create opportunities for career growth
At Citizenship Italia, Badanai and his team assess new hires not just on technical abilities but on initiative. Every candidate is given a vague task to see how they handle uncertainty. “The ones who succeed aren’t necessarily the most experienced, but the ones who take ownership, ask smart questions and communicate clearly,” Badanai says. That same proactive mindset fuels long-term growth—it’s the difference between waiting for opportunities and creating them.
But employees can’t do it alone. Leadership must create deliberate opportunities for career advancement, whether through mentorship, sponsorship or structured career development check-ins. Remote workers need more than encouragement. They need systems that ensure their contributions don’t go unnoticed.
Because in an office, visibility happens by chance. In a remote world, it happens by design. And the best leaders don’t just see their people—they make sure everyone else does, too.
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This article originally appeared in the May 2025 issue of SUCCESS+ magazine. Photo by Ground Picture/Shutterstock.
