The Remote Leadership Trap
A couple of years ago, I watched a very capable VP try to manage his newly remote team exactly the way he’d managed them when they all sat three cubicles away from each other. Daily check-ins became hourly Slack messages. “Open door policy” became “always available on video call.” Team bonding moved from coffee chats to mandatory virtual happy hours.
The team was miserable. Productivity tanked. And this leader, who’d been successful for years, couldn’t figure out what was going wrong.
Here’s what I told him, and what I’m telling you: The biggest mistake I see with remote teams is leaders who try to manage distributed people the same way they managed co-located ones. Different contexts require different approaches—and that’s where most fail.
Why Your Brain Fights This
Look, I get it. When you’ve spent years perfecting your leadership style, being told you need to completely rewire your approach feels like starting over. It’s disorienting as hell.
The issue is that remote work strips away everything you thought you knew about managing people. No more reading body language in meetings. No more sensing when someone’s having a rough day. No more spontaneous brainstorming sessions that happen because you bump into each other at the coffee machine.
All those management instincts you’ve developed have been based on physical presence. And now that presence is gone.
What Actually Changes (And Why It Matters)
When I started working with remote teams, I had to learn strategize the way I connected with my teams. And look, I’ll be the first to admit I was already at an unfair advantage because the vast majority of my team wasn’t location dependent way before remote working was a thing. For those transitioning into remote leadership, here’s what’s really different:
Communication becomes asynchronous whether you like it or not. Your team member in Singapore can’t wait for you to wake up in New York before making a decision. If you haven’t given them the framework to move forward independently, you’ve just created a bottleneck.
Trust has to be intentional, not accidental. In an office, trust builds through proximity. You see people working, you chat in hallways, you develop relationships naturally. With remote teams, trust gets built through transparency, consistent delivery, and clear communication. It doesn’t just happen.
Culture becomes something you create, not something that emerges. Office culture happened organically because you shared experiences. Remote culture requires you to be deliberate about values, rituals, and connection.
The Shift That Changes Everything
The leaders who figure this out make three critical changes:
- They stop managing presence and start managing outcomes. They don’t care when people work. They care about what gets delivered.
- They replace informal updates with structured communication. Instead of hoping to catch someone at their desk, they build systems for information flow.
- They move from being reactive firefighters to proactive framework builders. Rather than solving problems as they pop up, they create systems that prevent the problems in the first place.
Why Most Leaders Resist (And Why That’s Expensive)
This shift feels wrong. After years of equating “I can see them working” with “they’re being productive,” trusting people you can’t see requires a complete mindset overhaul. I’ve seen leaders burn through talented people because they couldn’t make this transition. They interpret “I can’t monitor them constantly” as “they must be slacking off”—when the real issue is they’re using the wrong success metrics.
Remote teams aren’t broken versions of office teams. They’re completely different ecosystems that need completely different leadership.
The sooner you accept that everything you knew about management needs an update, the sooner your team stops struggling and starts thriving.
So the question isn’t whether your team can work remotely. It’s whether you can lead remotely.
And if you can’t? Well, that’s not your team’s problem to solve–it’s yours.