How Modern Management of Remote Teams Is Getting Increasingly Difficult

Management is far more complex than I understood before stepping into the role. As an engineer, I viewed it mainly as task delegation and progress tracking. But experiencing both sides—as a team member and as a manager—has shown me how much I was missing. At KokuTech, I'm studying how technology can strengthen the relationships between managers and their teams, including the mentor-mentee partnerships that drive professional growth.

The Challenges

Relationship Management

Building a strong relationship with one person takes time and energy. Now multiply that across an entire team. Each team member brings their own aspirations, working style, and communication needs. Managers must maintain these relationships simultaneously while balancing individual growth with team objectives. It's relationship building at scale, and it's exhausting—yet crucial for team success.

Interest Alignment

In small startups or constrained teams, aligning individual interests with company needs becomes a daily puzzle. A developer might want to explore a new technology stack, but the company needs them focused on maintaining critical systems. An ambitious team member might seek leadership opportunities when the flat structure can't accommodate it. These misalignments create real tension, and managers must navigate them without burning out their team or derailing company objectives.

The reality is that perfect alignment rarely lasts. As people grow, their interests and goals evolve—sometimes faster than the company can adapt. Even when you find temporary balance, it's often just that: temporary. This perpetual realignment is perhaps one of the most draining aspects of management, and could explain why some great employees eventually move on despite having great managers.

Role Perception

The word "boss" often carries baggage—many people's first instinct is to see managers as obstacles or overseers rather than allies. This mindset creates invisible barriers: team members might hide problems until they're too big to solve, avoid asking for help, or miss growth opportunities out of fear or mistrust. Good managers spend significant energy trying to break down these misconceptions, proving through actions that their real job is to help their team succeed.

This is where technology could reshape the dynamic entirely. Instead of managers and reports falling into traditional power dynamics, imagine tools that create transparency and shared understanding from day one. A third-party perspective could help surface misalignments early, facilitate honest dialogue without the awkwardness of status relationships, and help both sides see the other's perspective more clearly. The goal isn't just to improve communication—it's to fundamentally change how these relationships form and evolve.

The Difficulty of Virtual Communication

The shift to remote work has magnified the challenges of effective communication. The subtle, yet critical, physical cues once picked up in face-to-face interactions are now lost. Managers must navigate these waters more cautiously, making extra efforts to read between the lines and understand the sentiments of their team members without the benefits of physical presence. What might have been a quick desk visit to gauge someone's mood now requires scheduled video calls, careful message crafting, and constant awareness of work-life boundaries.

Ways Forward

The complexities of management extend far beyond what I initially imagined after years of thinking I knew what it was. Each challenge—from relationship building to interest alignment to remote communication—represents an opportunity to rethink how we approach leadership. At KokuTech, I'm working to understand these dynamics and potentially will build tools that support both managers and their teams in navigating these relationships more effectively.

I definitely can't solve these challenges alone. Whether you're a manager grappling with these issues or someone who has experienced them from the other side, I'd love to hear your perspective. Reach out at james@kokutech.com and let's explore how we can collectively make these relationships healthier.

Thanks for reading,
James