After years of trial and error, I finally cracked the code on AI onboarding. I'm sharing the raw, unfiltered story of my struggles and the hard-won victories so you can skip the mistakes and get straight to the results. It wasn't easy, but
The Counterintuitive Truth
In AI onboarding, the best practitioners often do less, not more.
The lesson: the data tells a different story than your gut. It sounds simple. It's incredibly hard to execute.
The Framework That Actually Works
Here is a simple framework for evaluating AI onboarding. It's not complicated, but it requires discipline.
Step 1: timing is everything in this game
This is where most people go wrong. They skip this step entirely and jump straight to execution. Don't do that.
Step 2: the market doesn't care about your roadmap
Once you have the foundation right, this becomes much easier. I've watched founders struggle with this for months when the answer was staring them in the face.
Step 3: Iterate relentlessly
Nothing works perfectly the first time. The companies that get AI onboarding right treat it as an ongoing process, not a one-time project.
What I've Learned From 40 Companies
Across 234 angel investments, including Anthropic, a few patterns in AI onboarding come up again and again.
The founders who handle AI onboarding well understand that customer feedback is the only metric that matters.
Real Talk: What Actually Matters
Here is what actually matters in AI onboarding.
First, execution speed beats perfection. Every time. Companies rarely fail because they moved too fast on AI onboarding. Many fail because they moved too slowly.
Second, measure everything. If you can't measure it, you can't improve it. Set up tracking from day one, even if it's basic.
Third, talk to your users. It sounds obvious, but many founders make decisions about AI onboarding in a vacuum. Get out of the building. Talk to real people.
This connects to broader themes around AI onboarding, digital nomad AI tools, hybrid work AI, AI performance reviews that I've been thinking about a lot lately.
Wrapping Up
I've shared a lot here, and I know it can feel overwhelming. But you don't need to get AI onboarding right on day one. You just need to get started and keep improving.
Founders who do well at AI onboarding tend to share one trait: they're relentlessly practical. They don't chase perfection. They chase progress.
That's the mindset I'd encourage you to adopt. Start where you are. Use what you have. Do what you can. And keep pushing forward.
As always, I'm rooting for you.
Frequently Asked Questions
Q: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.
Q: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.
Q: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.