''' I still remember the early days of RemoteTeam. We were a small, scrappy group of engineers, scattered across the globe, trying to build something new. I thought I knew how to manage people. I was wrong. Managing a remote AI team is a completely different beast. I made a ton of mistakes, but I also learned a ton. Here are the 11 lessons that made the biggest difference.
1. Your best engineer is probably your worst manager.
This is a hard one to swallow. You have a rockstar engineer who can ship code faster than anyone else. So, you promote them to manager. And then everything falls apart. Why? Because the skills that make a great engineer are the opposite of the skills that make a great manager. Engineers are trained to solve problems themselves. Managers are trained to empower others to solve problems. It's a completely different mindset. I learned this the hard way when I promoted our best engineer to lead the team. He was a genius, but he couldn't delegate to save his life. He ended up burning out, and the team's morale plummeted. Now, I look for completely different traits in managers: empathy, communication, and a genuine desire to see others succeed.
2. Hire for slope, not y-intercept.
When you're hiring for a remote AI team, you need people who can learn and adapt quickly. The field is moving so fast that what you know today will be obsolete tomorrow. That's why I always hire for slope—how fast someone is learning—not y-intercept—what they already know. I once hired an engineer who had no formal AI experience, but he had a GitHub profile full of interesting side projects. He learned faster than anyone I've ever seen, and within a year, he was one of our top contributors. Don't get me wrong, experience is great. But in a remote setting, you need people who are self-motivated and can figure things out on their own. That's the slope.
3. Over-communication is the baseline.
In an office, you can get away with being a little sloppy with communication. You can just walk over to someone's desk and ask a question. In a remote team, that's not an option. You have to be incredibly deliberate about communication. That means daily stand-ups, weekly one-on-ones, and a constant stream of updates in Slack. It might feel like overkill, but it's the only way to keep everyone on the same page. We even have a rule: if you're stuck on something for more than 15 minutes, you have to ask for help. It sounds simple, but it's saved us countless hours of wasted time.
4. The right tool is worth 10 engineers.
I'm a huge believer in the power of tooling. The right tool can automate tedious tasks, streamline workflows, and make your whole team more productive. At RemoteTeam, we invested heavily in our internal tools. We built a custom deployment pipeline that let us ship code multiple times a day. We had a dashboard that showed us all our key metrics in real-time. It was a lot of work to build, but it paid for itself a hundred times over. Don't be afraid to spend money on tools. It's one of the best investments you can make.
5. Asynchronous work is a superpower.
One of the biggest advantages of a remote team is that you can hire people from all over the world. But that also means you have to deal with different time zones. The key is to embrace asynchronous work. That means writing everything down, recording meetings, and using tools that allow people to collaborate on their own time. It's a different way of working, but it's incredibly powerful. It allows you to tap into a global talent pool and give your team the flexibility to work when they're most productive.
6. Trust is your most valuable currency.
In a remote team, you can't look over someone's shoulder to see if they're working. You have to trust that they're doing their job. That means giving them the autonomy to make their own decisions and the flexibility to work in a way that's best for them. It can be scary at first, but it's the only way to build a high-performing team. When you show your team that you trust them, they'll repay you with their loyalty and hard work.
7. Culture is what happens when you're not in the room.
In an office, culture is easy. It's the free snacks, the ping pong table, the happy hours. In a remote team, it's a lot harder. You have to be much more intentional about building a strong culture. That means celebrating wins, recognizing people for their hard work, and creating opportunities for people to connect on a personal level. We used to do a virtual "show and tell" every Friday where people could share something they were working on, whether it was a side project or a new hobby. It was a small thing, but it made a big difference.
8. Your calendar is your most important tool.
When you're managing a remote team, your calendar is your best friend. It's the only way to make sure you're spending your time on the right things. I block out time for everything: one-on-ones, team meetings, deep work, even lunch. It might sound rigid, but it's the only way to stay sane. It also sets a good example for the rest of the team. When they see that you're being deliberate with your time, they'll be more likely to do the same.
9. You have to be a great writer.
In a remote team, most of your communication is going to be in writing. That means you have to be a great writer. You have to be able to articulate your ideas clearly, concisely, and persuasively. It's a skill that a lot of people overlook, but it's one of the most important skills a remote manager can have. I spend a lot of time on my writing. I edit everything I write, and I'm always trying to get better. It's that important.
10. Don't be afraid to fire people.
This is another hard one, but it's true. In a remote team, a bad hire can be toxic. They can drag down the whole team's morale and productivity. That's why you have to be quick to fire people who aren't a good fit. It's not fair to the rest of the team to keep them around. I've had to fire a few people over the years, and it's never easy. But every time I've done it, it's been the right decision for the company.
11. It's a marathon, not a sprint.
Managing a remote AI team is a long-term game. You're not going to build a high-performing team overnight. It takes time, patience, and a lot of hard work. There will be ups and downs. You'll make mistakes. But if you stick with it, you can build something amazing. I wouldn't trade my experience managing remote teams for anything. It's been one of the most rewarding experiences of my life. ''')) HBox(children=(FloatProgress(value=0.0, max=1.0), HTML(value=
Frequently Asked Questions
How were these items selected?
Each item on this list comes from direct experience, either from building my own companies or from patterns I've observed across the 200+ startups I've invested in. I prioritize practical, actionable items over theoretical concepts.
Can I implement all of these at once?
I'd strongly recommend against it. Pick the 2-3 items that resonate most with your current situation and focus there. Trying to do everything simultaneously is a recipe for doing nothing well.
Are these recommendations still relevant in 2026?
Absolutely. While specific tools and tactics change, the underlying principles remain consistent. I update my thinking regularly based on what I'm seeing in the market and across my portfolio companies.
How do I know which items apply to my situation?
Start by honestly assessing where your biggest bottleneck is right now. The items that address that specific constraint will give you the highest return on your time and energy.