Lessons in leadership, patience, conflict, and getting the most out of people — from someone who’s been leading remote teams for 20+ years
The Illusion of Leadership
I remember the first time I was officially in charge of a team. I had a title. I had a packed calendar full of Zoom calls. I had a long list of to-dos in a shared doc. And I had no idea what I was doing.
Nobody tells you how quickly you go from excitement to uncertainty. You think it’s about processes, systems, vision decks. And sure, those matter. But leading a real team — remotely, with real people, scattered across time zones and Slack threads — is more like being a part-time therapist, amateur mind reader, occasional referee, and full-time janitor of egos and miscommunications.
I thought leadership was going to be about strategy. Turns out, it was about people. And people are complicated — especially when you’re not in the same room.
The Myth of the “Perfect Team”
In my early years, I used to daydream about the “dream team” — the high-performing, low-maintenance group where everyone was self-motivated, always online at the same time, and somehow knew exactly what needed to be done without needing to be told.
Then I started managing real teams.
What I got instead were the brilliant but erratic ones. The quiet grinders who never chimed in on calls. The timezone-clashing lone wolves. The over-sharers on Slack and the ones you had to ping three times to get a response. All of them, at one time or another, were in my project channels, waiting for direction or feedback I didn’t always know how to give.
At first, I saw these things as problems. Now I see them as raw material. Teams aren’t born — they’re built. And not with perfect pieces. They’re built through hard conversations, earned trust, and a whole lot of patience.
You don’t manage a remote team like you run a machine. You manage it like you tend a garden — daily, with attention and adaptability.
Conflict Isn’t the Problem — Avoidance Is
Here’s a confession: I once let a personality issue simmer for six months between two team members on different continents. One was blunt and short in every message. The other was more diplomatic, preferring to take time to write long, nuanced responses. The tension built up across Slack threads and passive-aggressive comments in Asana.
Instead of addressing it, I told myself it would work itself out.
It didn’t. Instead, it poisoned the project. Tasks were delayed. Updates were skipped. One team member quietly rolled off the project. The other stayed, but disengaged. The damage was done.
What I learned is that conflict isn’t the issue. Unspoken conflict is.
Now, I address tension early — with a quick video call, a DM that starts with, “Hey, can we talk about something?” Most people just want to be heard. Once that happens, even tricky dynamics can shift.
One of the most effective leadership skills you can develop is the ability to normalize hard conversations — especially remotely, where silence can mean anything. Don’t assume. Ask.
Making Space for People to Be Great
One of my favorite team members of all time almost got passed over. She was quiet, never spoke up on team calls, didn’t post in threads often, and never asked for help. For the first few months, I honestly wasn’t sure if she was fully engaged.
Then a senior team member went offline for a week due to connectivity issues, and I asked her to help out on part of the project.
What she delivered blew me away. Not only was the work solid — it was thorough, insightful, and incredibly well-documented. She even flagged a bug in the workflow that had gone unnoticed for months.
I realized I’d been measuring engagement based on noise — not outcomes. I was so tuned into the chatty contributors that I’d overlooked someone doing deep, focused work off-camera.
Now, I make space — especially for the quiet ones. I ask direct questions. I follow up in DMs. I schedule time for 1:1s where they can talk without being “on” for the group. Growth doesn’t happen in public threads. It happens in the spaces where people feel seen.
The Leadership Shift — From Control to Coaching
There was a time I thought leadership meant solving every problem myself. I believed the best way to show value was to jump into threads with fixes, stay up late cleaning up roadmaps, and be the loudest voice in every Zoom.
That’s not leadership. That’s control.
The real shift came when I started coaching instead of directing. I stopped replying first. I started asking questions like, “What would you do?” or “What’s your take on this?” I gave people the reins — even when it felt risky.
And it paid off. My team got more confident. More creative. More invested.
Yes, it took longer sometimes. Yes, I had to fight the urge to step in. But the reward was a team that solved problems without me — and often better than I could’ve done alone.
If you’re the answer to every question in the channel, you’re not leading — you’re bottlenecking.
Team Culture Is Built in the Cracks
Culture isn’t created in onboarding documents or kickoff calls. It’s created in the daily stuff — the way you respond to mistakes in public channels, the tone you set in project threads, who gets looped in and who gets credit.
There was a time when our Slack had gone quiet. People were posting updates, but there was no energy. No jokes. No emojis. No real human interaction. Just deliverables.
I realized people didn’t feel safe engaging casually. They’d seen pushback get shut down, or jokes misinterpreted. That was on me.
We fixed it by adding intentional, lightweight rituals — a “fail of the week” channel where people shared experiments that flopped. A weekly async prompt like “What’s one small win this week?” It brought back the human side of our work.
Culture in a remote team is built through visibility, consistency, and care — not policies.
When It’s Not Working
Let’s be honest — sometimes it’s just not the right fit. Sometimes someone isn’t showing up. Or they’re showing up, but causing friction. Or they’re a solid individual contributor who just isn’t built for the team’s current needs.
I’ve let people stay on too long because I wanted to avoid the hard conversation. I’ve also offboarded too quickly, when I didn’t take the time to understand what was really going on behind the scenes.
Remote work can mask issues — or amplify them. You don’t see body language. You don’t “bump into” someone and get a gut check. You have to be intentional.
When someone’s not working out, be honest. Be fast. Be fair. And be human. If you’ve built a solid foundation, your team won’t fall apart when someone leaves — because they’ll trust that you’re protecting the whole, not playing favorites.
The hardest part of remote leadership is making people feel connected while still making hard calls. But if you wait too long, you risk losing more than one person.
Loneliness, Doubt, and Getting Through It
Leadership can be isolating — especially remotely. You’re in charge, but you’re alone in your home office. Your webcam becomes your window to the team, but sometimes it’s not enough.
I’ve had those days where I felt like I was carrying the weight alone. Where the team felt disconnected. Where projects were late and Slack was dead and I found myself wondering, “Am I failing here?”
In those moments, I’ve learned to reach out — to mentors, peers, even my own team. I’ve learned to be vulnerable, to say, “This feels hard right now. Let’s recalibrate.”
And I’ve learned to step away when needed — because burnout doesn’t announce itself. It creeps in through always-on work and never-off Slack.
If you’re leading remotely, protect your energy. You are the emotional tone-setter for the team, whether you realize it or not. Take care of yourself so you can take care of them.
The People Are the Point
In the end, it’s not about dashboards or roadmaps or velocity metrics. It’s about the people.
The ones who figure out workarounds. The ones who over-communicate when the Wi-Fi goes out. The ones who surprise you. The ones who grow, take flight, and go on to lead their own teams.
I once got a message from a former team member, years after we worked together. She thanked me for something I said in a Slack DM — just a small vote of confidence. She said it made her believe she could lead. She’s now heading up a team of her own.
That’s why we do this. Not to manage work — but to grow people. And in doing that, we build teams that don’t just ship — they shine.
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