It is easy to be wrong about AI transformation, and the mistakes teach the most.
You don’t have to be a tech expert to make AI work for your business. Here’s my simple, practical approach to leading AI projects that deliver real change.
Why Most Approaches Fail
Many common approaches to AI transformation are flawed at the root.
The root cause is usually one of three things:
Copying what big companies do without understanding why they do it. What works for Google doesn't work for a 10-person startup.
Over-engineering the solution when a simple approach would work better. I've seen teams spend six months building something that could have been done in two weeks.
Ignoring the human element. Technology is the easy part. Getting people to actually use it is where the real challenge lives.
The Counterintuitive Truth
In AI transformation, the best practitioners often do less, not more.
The lesson: customer feedback is the only metric that matters. It sounds simple. It's incredibly hard to execute.
What I've Learned From 56 Companies
A few patterns in AI transformation come up again and again.
The founders who handle AI transformation well understand that customer feedback is the only metric that matters.
The AI Angle
Any discussion of AI transformation in 2026 has to include AI. As someone who's invested in Anthropic, OpenAI, Scale AI, and Hugging Face, I have a front-row seat to how AI is transforming this space.
The short version: AI makes good practitioners better and bad practitioners worse. It's an amplifier, not a replacement.
Some teams use AI to get far more out of AI transformation. Others spend heavily on AI that solves the wrong problem. The difference comes down to understanding what you're actually trying to achieve.
This connects to broader themes around AI transformation leadership, chief AI officer, leading through uncertainty, AI change management that I've been thinking about a lot lately.
Final Thoughts
There are no shortcuts in AI transformation, but there are smarter paths.
The strongest teams treat AI transformation as a competitive advantage, not a checkbox. They invest in it early, measure it obsessively, and never stop improving.
If you're just getting started with AI transformation, don't be intimidated. Everyone starts somewhere. The key is to start with the right mindset and the right framework, and then execute like your company depends on it. Because it probably does.
Frequently Asked Questions
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: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.
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.