I’ve built and sold two companies and invested in over 200 more, including giants like Anthropic and OpenAI. I’ve seen the inside of how the fastest-growing companies in the world operate. And I can tell you, with absolute certainty, that almost everyone is thinking about async communication and AI in completely the wrong way.
People see AI as a tool for efficiency. A glorified transcription service. A meeting summarizer. That’s table stakes. It’s like using a supercomputer to run a calculator. The real revolution, the secret that the top 1% are quietly figuring out, is using AI to decode the human element within our digital conversations.
Forget everything you've read about async communication AI. I'm about to share a secret that will change how you work forever.
The Illusion of Connection
When we went remote, we traded the rich, high-bandwidth communication of an office for the low-bandwidth, text-based world of Slack, Teams, and email. We gained flexibility, but we lost something crucial: subtext. The subtle cues, the body language, the tone of voice that tells you what’s really going on.
We’ve tried to compensate with emojis and exclamation points, but it’s a poor substitute. The result? Misunderstandings fester. Resentment builds silently. Great ideas get lost in a sea of notifications. I saw this firsthand while building RemoteTeam. We were creating a platform to make remote work better, but even we struggled with the limitations of the tools we were using. A delayed response wasn't just a delay; it was a source of anxiety. A concisely worded message could be interpreted as passive-aggressive.
This is the silent killer of productivity and culture in a remote or hybrid setup. And most leaders are completely blind to it.
AI as the Subtext Decoder
Everyone is focused on using AI to analyze what is being said. The real opportunity is using AI to analyze how it’s being said. Imagine an AI that doesn’t just summarize a Slack channel, but tells you the underlying sentiment is shifting from positive to anxious. An AI that doesn’t just transcribe a performance review, but flags that the manager is using consistently negative framing, even with positive feedback, which is likely to demotivate the employee.
This isn’t about surveillance. It’s about insight. It’s about giving leaders the emotional and cultural context they’ve been missing since we left the physical office. It’s about rebuilding the connective tissue of a team.
At one of my portfolio companies, a small, fast-moving startup, they started using an early-stage AI tool for this. The AI flagged a conversation between two key engineers as having a high “frustration index.” On the surface, the messages were professional. They were debating a technical approach. But the AI picked up on the repeated use of certain phrases, the decreasing response times, the lack of positive reinforcement. The CTO was alerted, stepped in, and mediated a conversation. It turned out there was a fundamental disagreement about the product architecture that was causing massive friction. They resolved it. The project, which was on the verge of collapse, got back on track. That’s not something a simple summary tool can do.
The New Frontier: Culture Building and Performance
This is where it gets really interesting. We can now use AI to be proactive about culture and performance, not just reactive.
AI-Powered Culture Building: Instead of relying on gut feel and annual surveys, what if you had a real-time dashboard of your company’s cultural health? You could see which teams are collaborating well, where communication bottlenecks are forming, and which managers are fostering a positive environment. You could identify “culture champions” based on how they communicate and interact, and learn from them.
Fairer, Better Performance Reviews: Performance reviews are notoriously biased and subjective. AI can help level the playing field. By analyzing the language used in feedback, both from managers and peers, AI can identify patterns of bias. It can also provide a more holistic view of an employee’s contribution, looking at not just their individual output, but how they communicate, collaborate, and help others. This moves us from a purely output-driven model to one that rewards the kind of behavior that actually builds great companies.
This isn't some far-off future. The technology is here. The companies that are building this are among the most exciting in my portfolio. The challenge is no longer technical; it’s a mindset shift. We need to stop seeing AI as a tool for robots and start seeing it as a tool for humans.
The Wake-Up Call
I’m not saying this is easy. There are serious ethical considerations to navigate. Privacy is paramount. But the risk of doing nothing is far greater. The companies that stick to the old way of thinking, the ones that see AI as just an efficiency hack, will be outmaneuvered and out-innovated.
They will lose their best people, not because they don’t pay enough, but because their work environment is a black box of anxiety and miscommunication. The winners of the next decade will be the companies that use AI to build truly human-centric, psychologically safe, and high-performing remote and hybrid cultures.
So, the next time you think about async communication and AI, don’t just think about summaries and transcriptions. Think about subtext. Think about sentiment. Think about connection.
That’s the secret. That’s the future. And it’s coming faster than you think.
From Theory to Practice: How to Actually Implement This
This all sounds great in theory, but how do you actually start implementing this in your own company? It's not about flipping a switch. It's a gradual process of building trust and demonstrating value.
Start Small and Focused
Don't try to boil the ocean. Start with a single, specific problem. Maybe it's the communication overhead in your engineering team. Or perhaps it's the high rate of misunderstandings in your customer support department. Pick one area where the pain is most acute.
I remember when we first started building RemoteTeam. We didn't set out to solve every problem with remote work at once. We started with a simple, painful problem: payroll for a globally distributed team. We solved that, built trust, and then expanded from there. The same principle applies here. Start with a small, focused pilot project. For example, use an AI tool to analyze the communication patterns in a single Slack channel for a month. Measure the results. Did it lead to faster problem resolution? Did team morale improve? Use that data to make the case for a wider rollout.
Choose the Right Tools
The market for these tools is still nascent, but it's evolving quickly. When evaluating tools, don't be dazzled by fancy features. Focus on the fundamentals:
- Privacy and Security: This is non-negotiable. The tool must have robust privacy controls. You should be able to control what data is analyzed and who has access to the insights. Anonymization and data aggregation are key features to look for.
- Actionability of Insights: The tool shouldn't just give you data; it should give you actionable insights. If it tells you a team is feeling anxious, it should also suggest potential reasons why and offer concrete steps you can take to address the issue.
- Integration: The tool should seamlessly integrate with your existing communication platforms, whether it's Slack, Microsoft Teams, or email. The last thing you want is another tool that your team has to learn and manage.
Be Transparent with Your Team
This is probably the most important point. You cannot and should not implement these tools in secret. That's a recipe for disaster. You need to be radically transparent with your team about what you're doing and why.
Explain the problem you're trying to solve. Explain how the tool works. And most importantly, explain what's in it for them. This isn't about Big Brother watching their every move. It's about creating a better, more supportive, and more effective work environment for everyone. Frame it as a tool to help them, not to monitor them.
When I invested in Scale AI, one of the things that impressed me most was their commitment to a human-in-the-loop approach. They understood that AI is most powerful when it's used to augment human intelligence, not replace it. The same principle applies here. This is about augmenting the emotional intelligence of your leaders and your team.
The Future is Emotionally Intelligent
For the past decade, the focus of workplace technology has been on productivity and efficiency. We've been obsessed with optimizing workflows and automating tasks. That's all well and good, but we've reached a point of diminishing returns. The next great leap in productivity will come from a different source: emotional intelligence.
The companies that thrive in the coming years will be the ones that understand the human element of work. They will be the ones that use technology not just to make us more efficient, but to make us more connected, more empathetic, and more human.
This isn't just a prediction; it's a roadmap. It's a call to action for every leader who wants to build a company that is not only successful but also a great place to work. The tools are here. The time is now. The only question is: are you ready to lead the way?
Frequently Asked Questions
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.
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.
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.