I once had a brilliant machine learning engineer, let’s call him Alex, who was based in a completely different time zone. For weeks, his performance had been stellar. Then, suddenly, his productivity dropped off a cliff. He missed deadlines, his code quality suffered, and he became quiet in our team channels. My initial reaction was frustration. I almost sent him a harsh email. But then I remembered one of the most important lessons I’ve learned in my career: assume good intentions.
Instead of a reprimand, I sent him a simple message: “Hey, is everything okay?” It turned out his father was seriously ill. We worked out a more flexible schedule for him, and within a few weeks, he was back to his brilliant self. This experience, one of many, has shaped my approach to managing remote teams, especially in the high-stakes world of AI development.
For the last five years, I’ve been leading a fully remote AI team. It’s been a journey full of challenges I never anticipated. Here are five of the most counterintuitive lessons I’ve learned about communication, trust, and productivity when your team is scattered across the globe.
1. Overcommunication is a Myth; Clarity is Everything
When we first went fully remote, I was terrified of micromanaging. I thought that if I trusted my team, I should just let them get on with it. I was wrong. In a remote setup, you can’t just swing by someone’s desk to clarify a small point. What seems like a minor misunderstanding can snowball into a major problem.
I quickly learned that there’s no such thing as overcommunication. There is, however, such a thing as unclear communication. Now, I’m a stickler for clarity. We have a “single source of truth” for every project, usually a detailed document that outlines the goals, specs, and deadlines. We use a combination of synchronous and asynchronous communication tools. We have daily stand-ups, but they’re not for status updates. They’re for unblocking each other. We also have a dedicated Slack channel for “stupid questions.” There are no stupid questions when you’re working on complex AI models.
This focus on clarity has had a huge impact. It’s reduced rework, improved our velocity, and, most importantly, it’s made everyone feel more confident and connected. We’re not just a collection of individuals working in isolation. We’re a team, and we’re all on the same page.
2. Trust is Built on Actions, Not Words
Everyone talks about the importance of trust in a remote team. But how do you actually build it? You can’t just say “I trust you” and expect that to be enough. Trust is built on a foundation of consistent, reliable actions.
For me, this means a few things. First, I’m transparent with my team. I share the good news and the bad. I talk about the challenges we’re facing as a company, and I’m honest about my own mistakes. Second, I empower my team to make decisions. I don’t need to be in every meeting or approve every small change. I hire smart people, and I let them do their jobs. Third, I’m always available. My team knows that they can reach out to me at any time, and I’ll do my best to help them.
I once had to make a tough call to pivot a project we’d been working on for months. It was a blow to the team’s morale. But because we had built a foundation of trust, we were able to have an open and honest conversation about it. The team understood the reasons for the decision, and we were able to move forward together. That’s the power of trust.
3. Asynchronous Work is a Superpower, But It Needs Structure
One of the biggest advantages of a remote team is the ability to work asynchronously. It allows you to hire the best talent, regardless of their location. It also gives your team the flexibility to work when they’re most productive. But asynchronous work can also be a recipe for chaos if you don’t have the right structure in place.
We’ve found that a few key practices are essential for making asynchronous work a success. First, we have a clear process for everything, from code reviews to bug reports. This ensures that everyone knows what’s expected of them, and it prevents things from falling through the cracks. Second, we’re religious about documentation. Every decision, every discussion, every line of code is documented. This makes it easy for team members in different time zones to stay in sync. Third, we use tools that are designed for asynchronous collaboration. We’re big fans of tools like Notion, Loom, and, of course, our own products at RemoteTeam.
It’s not always easy. There are times when I miss the energy of an in-person brainstorming session. But the benefits of asynchronous work far outweigh the challenges. It’s allowed us to build a world-class team and create some truly innovative AI products.
4. The Best Ideas Can Come From Anywhere
In a traditional office environment, it’s easy for the loudest voices to dominate the conversation. The introverts, the remote workers, the people who are just having a bad day—their ideas can get lost in the shuffle. In a remote team, you have the opportunity to level the playing field.
I make a conscious effort to solicit feedback from everyone on my team. I use anonymous surveys, I have regular one-on-ones with every team member, and I’ve created a culture where it’s safe to disagree. Some of our best ideas have come from the most unexpected places. A junior engineer in Eastern Europe pointed out a flaw in our data pipeline that saved us months of work. A designer in South America came up with a brilliant new feature that has become one of our most popular.
As a leader, it’s my job to create an environment where everyone feels comfortable sharing their ideas. It’s not about having all the answers. It’s about creating a space where the best ideas can win, no matter where they come from.
5. You Have to Be Intentional About Culture
In an office, culture happens organically. It’s the inside jokes, the shared lunches, the after-work drinks. In a remote team, you have to be much more intentional about building a strong culture. You can’t just assume it will happen on its own.
We’ve tried a lot of different things to build our remote culture. We have virtual coffee breaks, we play online games together, and we have a #random channel in Slack where we share pictures of our pets and our weekend adventures. We also have an annual offsite where we all get together in person. It’s a chance to connect on a deeper level and to remind ourselves that we’re all part of something bigger.
It might sound cheesy, but these things matter. They’re what turn a group of individuals into a cohesive team. They’re what make people want to come to work in the morning. And in the competitive world of AI, a strong culture is one of your biggest competitive advantages.
The Journey Continues
Managing a remote AI team is not for the faint of heart. It requires a different set of skills than traditional management. It requires more trust, more clarity, and a lot more intentionality. But if you’re willing to put in the work, the rewards are immense. You get to work with the best people in the world, you get to build amazing products, and you get to create a new model for what work can be.
I’m still learning. I’m still making mistakes. But I’m more excited than ever about the future of remote work and the incredible potential of AI. The journey is just beginning.
Frequently Asked Questions
How can I apply this thinking to my own situation?
Start by identifying the core principle behind the opinion, not the specific example. Then ask yourself: does this principle apply to my context? If yes, test it in a small, low-risk way before going all in.
What's the most common pushback you get on this?
People often push back by citing exceptions or edge cases. And they're usually right that exceptions exist. But building a strategy around exceptions rather than patterns is a losing game for most founders.
Do all experts agree with this view?
No, and that's fine. The best ideas in business are often contrarian. I share my perspective based on my experience and data, but I encourage you to seek out opposing viewpoints and form your own conclusions.
What experience informs this perspective?
This perspective comes from over a decade of building companies in Silicon Valley, two successful exits (RemoteTeam to Gusto, MovieLaLa to Gfycat), and investing in 200+ startups including Anthropic, OpenAI, and Scale AI. I write about what I've lived.