Everyone thinks they know AI onboarding, but they're missing the most important piece of the puzzle. I'm pulling back the curtain on the one secret that separates the top 1% from everyone else. This might be controversial, but the data does
The Counterintuitive Truth
In AI onboarding, the best practitioners often do less, not more.
The lesson: your team matters more than your technology. It sounds simple. It's incredibly hard to execute.
What I've Learned From 92 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 the best solutions are often the simplest ones.
What I Tell Founders
Before deciding anything about AI onboarding, start with three questions:
What's your timeline? Because the right approach for a company with 6 months of runway is very different from one with 3 years.
What have you already tried? Most founders have tried something. Understanding what didn't work is often more valuable than knowing what might.
Who on your team owns this? If the answer is "everyone" or "no one," that's your first problem to solve.
These questions seem simple but they reveal a lot about where a company actually stands.
This connects to broader themes around hybrid work AI, AI performance reviews, async communication AI, AI culture building 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 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 234 startups I've invested in. I prioritize practical, actionable items over theoretical concepts.
Q: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.
Q:Which item on this list has the highest impact?
It depends on your stage and context, but in my experience, the items near the top of the list tend to have the broadest applicability. That said, sometimes the less obvious items create the biggest breakthroughs for specific situations.
Q: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.