You’re probably using async communication AI all wrong. I was too. Here's the painful story of how I learned to do it right.
I once lost a star engineer because of a poorly worded Slack message. It was a classic case of async communication gone wrong. A misunderstanding snowballed, and before I knew it, one of my best people was walking out the door. That was a wake-up call. It forced me to rethink everything I thought I knew about remote work and communication.
Most people think of async communication AI as a simple tool for scheduling meetings or summarizing conversations. That’s like using a supercomputer to play tic-tac-toe. The real power of async AI isn’t in these surface-level applications. It’s in deeply integrating AI into the very fabric of your company’s workflows.
The Big Misconception
When I sold RemoteTeam to Gusto, I had already spent years obsessing over remote work. We built tools to help teams collaborate across time zones. But even I was missing the biggest piece of the puzzle. I was focused on the tools, not the system.
Everyone is clamoring for the latest AI gadget. A new chatbot, a new transcription service, a new project management tool with "AI-powered" features. These are all fine, but they are just incremental improvements. They don’t fundamentally change the way we work.
The Secret: Deep Workflow Integration
The real revolution is in using AI to automate and improve complex, human-centric workflows. I’m talking about things like onboarding new employees, conducting performance reviews, and even fostering a company culture. These are the areas where async communication breaks down most often, and where AI can have the biggest impact.
At one of my portfolio companies, we built an internal tool that used AI to guide new engineers through their first 90 days. It wasn’t just a checklist of tasks. It was a personalized learning path, with AI-powered mentors, code review feedback, and even social prompts to connect with other team members. The result? New hire retention went up by 30%.
AI in Onboarding: Your New Secret Weapon
Think about your current onboarding process. It’s probably a mix of documents, videos, and a few scheduled meetings. It’s a one-size-fits-all approach that bores your best people and overwhelms everyone else.
Now, imagine an onboarding process that adapts to each new hire. An AI that can answer their questions in real-time, point them to the right resources, and even identify areas where they are struggling. This isn’t science fiction. This is what’s possible with today’s technology.
Here’s a simple example. You can use a large language model to create a personalized onboarding plan for each new hire based on their role, experience, and even their learning style. You can feed the model your company’s entire knowledge base, and it will create a customized curriculum for the new employee.
The Controversy: AI in Performance Reviews
This is where things get spicy. The idea of using AI in performance reviews makes a lot of people uncomfortable. They picture a cold, heartless robot judging their work. But that’s a complete misunderstanding of how this should work.
I’ve seen too many performance reviews that are based on gut feelings and personal biases. A manager has a good relationship with an employee, so they get a glowing review. Another manager is having a bad day, and their direct report pays the price. It’s a broken system.
AI can bring a level of objectivity and data-driven analysis that is simply not possible for humans. An AI can analyze a developer’s code contributions, a salesperson’s CRM data, or a marketer’s campaign results. It can identify patterns and trends that a human manager would never see. This doesn’t mean the AI makes the final decision. It means the manager is armed with better data to have a more productive and fair conversation.
My 2024 Prediction
The companies that win in the next few years will be the ones that master the art of async communication AI. They will move beyond the simple tools and build deep, integrated systems that automate and improve their most critical workflows.
This will have a profound impact on hybrid work and digital nomads. It will enable teams to be more distributed than ever before, while still maintaining a high level of alignment and productivity. The 9-to-5 workday, with its endless meetings and interruptions, will finally die.
This isn’t just about efficiency. It’s about creating a better way to work. A way that is more flexible, more personalized, and ultimately, more human.
So, my challenge to you is this: stop tinkering with the latest AI toys. Start thinking about how you can fundamentally redesign your company’s workflows with AI at the core. That’s the secret to building a world-class organization in the age of AI.
Frequently Asked Questions
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.
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 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.
How has this view evolved over time?
My thinking on most topics has changed significantly over the years. Early in my career, I held many conventional views that experience proved wrong. I try to update my beliefs when the evidence changes.