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August 27, 2026

Episode 7: Your AI Is Already Learning. The Question Is…What Are You Teaching It?

I don’t think most companies realize they’re training their AI every single day.

Not in the formal sense. I’m not talking about model fine-tuning or reinforcement learning. I’m talking about something much simpler.

Every time a salesperson responds to an objection…
Every time Customer Success saves an account…
Every time Engineering solves an issue…
Every time Procurement negotiates a contract…

…your organization is demonstrating how it thinks.

The question is whether anyone, or anything, is paying attention.

I’ve started thinking about AI less like software and more like the new employee who quietly sits in the corner of every meeting. At first, they don’t contribute much. They mostly listen. They watch how decisions get made. They learn who usually has the right instincts. They notice which problems keep coming back. They begin to understand the difference between what’s written in the process manual and what actually happens when customers call with a real problem.

Here’s the part I don’t think enough executives are talking about.

Most organizations aren’t intentional teachers.

We assume our culture gets passed down naturally.

We assume new employees “pick things up.”

We assume good judgment spreads through experience.

Sometimes it does.

Sometimes it doesn’t.

If AI is going to become part of how companies operate, then we have to become much more deliberate about what we’re teaching it. Because AI isn’t just learning our best practices. It’s also learning our bad habits. It learns unnecessary approval chains. It learns inconsistent pricing decisions. It learns workarounds that employees invented years ago because nobody ever fixed the underlying process. Left unchecked, AI doesn’t just preserve excellence. It preserves dysfunction too.

That’s why I don’t think building a Company Brain is simply about capturing knowledge.

It’s about deciding which knowledge deserves to live on.

Every organization has habits.

Some create competitive advantage.

Others create technical debt.

AI doesn’t automatically know the difference.

We have to teach it.

And maybe that’s the next leadership skill.

Not managing people.

Not managing technology.

Managing what your organization chooses to remember.

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