Managing a remote team? Struggling to keep everyone aligned, engaged, and productive? You’re not alone. Remote work is here to stay – 98% of remote workers want it long-term. But managing a distributed team isn’t just about moving office dynamics online. The best managers adapt, refine, and lead with confidence.

The good news? You don’t need a brand-new playbook. Leadership, communication, and culture still matter. We’ve gathered insights from top remote managers, breaking down what works and why. Ready to level up your remote leadership? Dive in, learn from the best, and start seeing real results today.

The Challenges of Managing Remote Teams: Why It’s Harder Than You Think

Remote work isn’t just a logistical shift—it’s a cultural one. Without the physical presence of an office, managers face a host of challenges that can impact productivity, morale, and team cohesion. Phil Montero, Director of Events and Field Marketing at Model, said the biggest change is how managers measure their team's work: 

“The biggest difference is a shift in management style from “eyeball management” (assuming workers are being productive because you physically see them at their desks working) to managing by results.”

Communication Breakdowns

In an office, a quick chat by the water cooler or a spontaneous meeting can resolve issues in minutes. In a remote setting, communication becomes fragmented, asynchronous, and often impersonal. Time zone differences worsen the problem, with team members waiting hours or even days for responses. 86% of virtual teams have experienced communication difficulties. Without non-verbal cues like body language and tone, messages can easily be misinterpreted, leading to frustration and inefficiency.

Building Trust Without Face-to-Face Interaction

Trust is the foundation of any successful team, but it’s harder to build when you can’t see your colleagues every day. In an office, you can see when someone is not at their desk. You can see if someone is slacking off. In remote work, your colleague could be playing video games or painting a landscape. You can never know for sure.

In this context, managers often struggle with the balance between giving autonomy and ensuring accountability. Francesca Pinder, Marketing Manager at The Influencer Room mentioned:

‍“If you’re still tracking hours in a remote team, you’ve already lost. Focus on results, not screen time. Give people space, trust them to get sh*t done, and hold them accountable for actual work, not just looking busy.”

Maintaining Productivity Without Micromanaging

It’s a phrase that has become slightly oversaturated these days. However, Stephanie Ruhle says:

“Work-life balance is not just a buzzy, self-help term that real business people laugh at. You need it.”

Remote work offers flexibility, but it also blurs the line between work and personal life. Employees may feel pressured to be “always on” to prove they’re working, leading to burnout. On the flip side, managers may worry about whether their team is staying focused. This disconnect can lead to disengagement and reduced productivity. David Heinemeier Hansson, Author of Remote: Office Not Required, claims:

‍“Workers at 37signals needn’t ask permission to go on vacation or specify how much time they’ll take. We tell them: just be reasonable, put it on the calendar, and coordinate with your coworkers. If you let them, humans have an amazing power to live up to your high expectations of reasonableness and responsibility.”

Effective remote managers do not micromanage but instead practice “micro-understanding.” This means staying integrated into workflows, anticipating challenges, and offering support without excessive oversight. One manager described this balance well: “Transferring the responsibility to the team members allowed me to take a step back and observe patterns on the issues that I could then specifically attend to.”

Fostering Team Cohesion and Culture When Managing Virtual Teams

One of the biggest challenges of remote work is maintaining a sense of belonging. Without shared physical spaces, team members can feel isolated and disconnected. A Gallup survey revealed that only 20% of remote workers feel strongly connected to their organization’s culture. Building a strong team culture requires intentional effort – something that doesn’t happen organically in a virtual environment.

‍Strategies for Success: How to Lead a Thriving Remote Team

Remote management is the same but different. A remote manager summarized it well: “It’s like learning to drive on the wrong side of the road… You have to get to the same destination, but with different signals, cues, and controls.”

While the challenges are real, they’re not insurmountable. Here are actionable strategies to help you lead your remote team effectively:

1. Master the Art of Communication

There is no one way to communicate. Some people appreciate a phone call – to be heard. Some people want a concise message – to be directed. Some people like to be left alone – to be trusted. It’s important to identify what your people need and extend them that consideration as and when you can. 

Effective communication is the cornerstone of managing a team remotely. Start by establishing clear protocols. For example, use Slack for quick updates, email for formal communication, and video calls for brainstorming sessions or sensitive discussions. Tools like Loom (for video messages) and Miro (for collaborative whiteboarding) can also enhance communication. 

“The most important keys to remote work at a startup have been weekly stand-ups. At Hive, we all get on Zoom once a week to chat and give shoutouts to the team. We also have regular one-on-ones with video on. Having your video on totally changes the tone of a meeting and is critical for a startup.” – John Furneaux, CEO of Hive

The key to remote communication is being available, not intrusive; be visible, approachable, and proactive in problem-solving, without overwhelming with constant check-ins.

2. Build Trust Through Transparency and Autonomy

Trust is earned, not given. Start by setting clear expectations and goals, then give your team the autonomy to achieve them. Regular check-ins are important, but they should feel supportive, not intrusive.

“We like to give people the freedom to work where they want, safe in the knowledge that they have the drive and expertise to perform excellently, whether they are at their desk or in their kitchen. Yours truly has never worked out of an office, and never will.” – Richard Branson, Founder of Virgin Group 

Consider implementing OKRs (Objectives and Key Results) to align your team around shared goals. This approach not only fosters accountability but also empowers employees to take ownership of their work.

Trust and flexibility are key to a healthy remote work culture, says Szokratesz Kosztopulosz, Events and Operations Manager at Toggl Track. Toggl empowers employees to manage their time and focus on results, fostering work-life balance. To maintain team cohesion, they invest in in-person meetups, strengthening relationships and boosting productivity. As Kosztopulosz puts it, “Relationships are built in person and maintained online.” By prioritizing trust, flexibility, and meaningful connections, Toggl shows how remote teams can thrive with unity and purpose.

Remote managers must shift from being enforcers to enablers. Instead of tracking hours, the focus should be on removing barriers, facilitating collaboration, and guiding teams toward results. Employees appreciate managers who trust their expertise and provide strategic guidance rather than dictating their every move. One employee remarked: “I never once felt that [my boss] was monitoring me—I always felt her as a resource.”

3. Prioritize Well-Being and Work-Life Balance

‍“Working from home makes it much harder to delineate work time from personal time. I encourage all of our employees to have a disciplined schedule for when you will work, and when you will not, and to stick to that schedule.” – Dan Springer, CEO of DocuSign

The thing about old-fashioned on-site work is that once you went home for the day, you were no longer at work, and therefore no longer working. There was a physical barrier as well as a figurative one. The work from home era has broken that work-home boundary entirely – work is home, and home is work. That means that it’s easier to make calls, emails, and messages to your team. And, it’s understandable. As a manager, you want to push for bigger and better results, all the time. However, you need to resist temptation and respect someone outside of office hours. 

‍“In the right roles and with the right people, flex does offer tremendous productivity improvement. It gives people time to process properly. Moreover, it gets them out of the office in terms of being bogged down in day-to-day admin. So there is more thought leadership that comes to the table, and that’s where your creativity and innovation come in.” – Osman Khan, Co-founder & CEO of Paddle

It’s easier said than done. But here’s one idea that has been slowly gaining traction is ‘No Meeting Fridays’. It gives employees uninterrupted time for deep work or personal errands. This might seem like a fluffy idea designed to pander and to get out of obligations, and some might see it that way. But research shows that there’s something here: Employee productivity was 71% higher when meetings were reduced by 40%. In short, encourage your team to set clear work hours and take regular breaks.

But before we move on, one last word on work-life balance: not every employee wants it. Some people are workaholics. It’s your job as a manager to know when to let people push themselves. 

4. Cultivate a Strong Team Culture

Company culture is too often empty corporate buzzwords. It’s all good to have a PowerPoint you show recruits telling them what you’re all about. But then they discover quite quickly that it’s a myth. Sometimes it’s propaganda, and that’s not nice. But sometimes, company culture is sincere, and the trouble is putting it into practice. Your daily work duties come first, we get that. But there lies the issue. Culture is only real when it’s put into practice. 

Start by creating opportunities for informal interactions. Virtual coffee chats, online games, or even a dedicated Slack channel for non-work conversations can help build connections. For deeper bonding, consider organizing team-building retreats. These off-site gatherings provide a rare opportunity for remote teams to connect in person, recharge, and align on shared goals.

‍"We wanted to give our team more clarity on and mobilize everyone around the company vision. Having the Serbian mountainside and wilderness serve as the backdrop for this was a complete success: the team is energized and excited to move forward!" – Kenneth Hellem, CPO of Ultimate Beauty

5. Anticipating the Challenges of Managing a Remote Team: Stay Ahead, Not Behind

The best managers don’t chase problems when managing a team remotely, they see them coming. Without the casual, in-office cues that signal when someone’s struggling, small issues can snowball fast. The trick? Spot patterns early and act before problems grow.

If a usually engaged employee goes quiet on Slack, if emails become abrupt, or if meetings feel more like monologues than discussions, something’s off. One manager put it best: “By noticing shifts in tone and response times, I could sense when my team needed support—before they even said a word.”

But, spotting the problem is one thing. How to prioritize it is another. Without clear direction, small frustrations turn into major roadblocks. Try using the Mosquito, Quicksand, and Dragon model:

• Mosquito issues? Fix them fast, don’t let them fester.
• Quicksand problems? Slow enough to manage, but they’ll sink you if ignored.
• Dragon crises? Drop everything and deal with them now.

Finally, don’t wait for someone to raise their hand – build check-ins into your rhythm. Regular, structured feedback keeps projects on track and prevents minor hiccups from becoming full-blown disasters.

The Role of Retreats in Remote Team Management

The tools, techniques, tips, and experts we offered above are great for managing remote teams. But nothing beats the power of in-person connections. That’s why corporate retreats are booming in the context of organizations going remote. Because, for remote-first teams, off-sites have become the new on-sites. Therefore, going remote is the saving – going on a retreat is the investment.

Now, if you take a leisurely scroll through our case studies, you’ll see a recurring theme,  time and time again. Teams are using retreats to beat the four challenges we outlined above: communication, trust, productivity, and culture. 

Whether it’s a weekend getaway in the countryside or a week-long retreat in Europe, these experiences can transform your team’s dynamics. The importance of getting people together in person, though each does it at their own pace. Some gather once every two years, others annually. For daily.dev, twice a year feels just right. This latest retreat was their sixth, and with each one, Dafna finds it less like “going away for work” and more like “meeting up with friends.”

‍“In each retreat, we can feel the effect of meeting up, and our connections deepen from one retreat to the next.” – Dafna Ran, Head of People at daily.dev

By stepping away from daily routines, teams recharge, align on goals, and build lasting bonds. As OnsiteHub emphasizes, a well-planned retreat with clear objectives can transform team dynamics and boost motivation. Learn more about the power of retreats here.

Conclusion: Leading with Empathy and Adaptability

Managing remote teams takes skill, trust, and adaptability. Get communication and culture right, and your team will thrive. Nothing beats the power of bringing them together in person. A retreat isn’t just a break – it’s the ultimate solution. Book a free consultation today and plan a retreat that transforms your team – let’s get started!