Episode 13: I Drew Two Circles on a Whiteboard Last Week…
Last week I was in a strategy session, and I found myself doing something I didn’t plan to do.
Instead of opening PowerPoint, I walked over to the whiteboard and drew two circles.
In the first circle I wrote:
Data
In the second I wrote:
Experience
Then I asked the room a simple question.
“If our AI lost one of these tomorrow…which one would hurt more?”
At first, everyone pointed to the first circle.
Makes sense.
Data is expensive.
Data is regulated.
Data is hard to collect.
Then we started talking.
What if your AI forgot every customer conversation from the past five years?
What if it forgot every implementation lesson?
Every pricing negotiation.
Every support pattern.
Every engineering decision.
Every project retrospective.
Every successful sales play.
Would you still feel like you had everything that mattered?
The room got quiet.
Because the answer wasn’t obvious anymore.
That’s when I realized we’ve been using the word “data” to describe two completely different things.
One is information.
The other is accumulated experience.
Information tells you what happened.
Experience helps you decide what to do next.
Those aren’t interchangeable.
One of the reasons your best employees become your best employees isn’t because they know more facts than everyone else.
It’s because they’ve seen enough situations that they recognize patterns before anyone else does.
That’s experience.
Now imagine your AI quietly building that same kind of experience over years.
Not replacing your experts.
Learning alongside them.
Helping the next employee benefit from what the last employee already figured out.
That’s a very different vision than “AI answers questions.”
It’s closer to organizational apprenticeship.
Maybe that’s where we’re headed.
Maybe the next generation of enterprise AI won’t be measured by how much information it contains.
Maybe it’ll be measured by how much experience it has accumulated.
I’ve been thinking about those two circles ever since.
I’m honestly not sure we spend enough time talking about the second one.
