Your Best Employee Might Also Be Your Best AI Teacher

Every company has that one employee. You know the person. Something goes wrong, everyone spends two hours trying to figure it out, and someone finally says:

“Has anybody asked Dave?”

Dave walks in. Looks at the problem. Asks two questions.

“Yeah, I’ve seen this before.”

Five minutes later, everyone wonders why they didn’t call Dave in the first place.

We introduced Dave earlier in this series because he represents something every organization depends on.

Experience.

But I’ve been thinking about Dave differently lately.

What if Dave’s greatest contribution to the company isn’t just solving problems?

What if it’s teaching the company’s AI how to solve them?

Think about how we train new employees.

We give them documentation. Assign training courses. Introduce them to the team.

Then, if we’re smart, we have them spend time with our best people.

Why?

Because watching an experienced employee handle a difficult situation teaches you things that never appear in the training manual.

You see which questions they ask.

What they ignore.

When they push back.

When they decide something isn’t worth pursuing.

And sometimes, when they admit they don’t know the answer.

That’s how professional judgment develops.

Now imagine doing something similar with AI.

Instead of simply uploading Dave’s documents, we capture examples of the problems he solves.

We ask him to review the AI’s recommendations.

When the AI gets something wrong, Dave explains what it missed.

When the AI gives two possible answers, Dave identifies the better one and explains why.

Over time, those examples and evaluations can help improve the system.

Sometimes through better retrieval and company-specific memory.

Sometimes through fine-tuning or reinforcement learning.

And sometimes by simply identifying situations where the AI should stop and ask an experienced person for help.

There’s an important distinction here.

Dave isn’t magically transferring everything in his head into a computer.

His experience has to be translated into useful examples, feedback, and evaluation criteria.

That’s difficult work.

But it’s also an opportunity we’ve never really had before.

One Dave can only help so many people.

He has meetings. Customers. Projects. A family.

And occasionally, he’d probably like to take a vacation without someone calling to ask why a spreadsheet stopped working.

But imagine if 500 employees could benefit from the lessons Dave has accumulated.

Not by replacing him.

By making more of his experience available to everyone.

I’ve spent more than 20 years in enterprise technology, and one thing I’ve learned is that great people make an enormous difference.

The challenge has always been scaling what makes them great.

Maybe AI gives us a new way to do that.

And maybe the next time something goes wrong, the answer won’t always be:

“Call Dave.”

Maybe it’ll be:

“Let’s see what Dave already taught us.”

 

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