How to Run AI Training Your Team Keeps Using

A month after I ran a company-wide training session for a natural skincare company, I was on a call with their president. A few minutes in, he mentioned that most of the team had recently switched to the same AI assistant. He thought the session had probably kicked it off. For a lot of his people, he said, it was the first time they had really thought about it.

I often say that nobody opens the AI tool you bought them, and that more training is not an adoption plan. I still believe both. This is the other half of that argument. Training is where adoption starts. It just cannot be where it ends.

What made that session stick

Two things, and neither of them was the slides.

It came after discovery. We had run a full discovery there, interviewing people across the company, so I walked in knowing what their week looked like: forecasting, orders, creative requests, and the handoffs between them. People do not adopt a tool because it is impressive. They adopt it because they watched it do a piece of their own Tuesday.

And it gave the company one default. Before the session, the open question was which assistant to use. Afterwards the team largely settled that on its own. It sounds small. It removes the most common reason people never start, which is not knowing where to start.

What a session like that cannot do by itself is change a workflow. It changes what people reach for when they sit down. The work moves when a system arrives, which is why the session there was one part of the engagement, alongside a couple of builds, and not the whole of it.

The sales team, and what followed

In April we trained the sales team at a licensed apparel company, about fifteen people in the room.

Then the systems came, and they came to where the team already works. A brief for each sales meeting, written into the calendar invite, with what the account has bought this year and across the whole relationship. A proposal and pricing deck generator, which shipped in June. The day after it went out, the director of sales wrote to say it was exactly what he had in mind.

I am not going to claim the training built those systems or made them work. My read is that it made the team ready to judge them. A salesperson who has spent an afternoon using an assistant on real work knows what a good draft looks like and what a lazy one looks like. When the proposal tool arrived, the director of sales had a view on it within a day, and a clear view from the person who will use it is what a build needs in its first month.

Training with no system behind it is an interesting afternoon. A system with no training behind it gets used, but it gets questioned late, after the habits have set.

One-to-one, for the person who will build

The third kind is the one I get asked about least. In February I ran one-to-one build sessions for the founder of a hardwood flooring company. Not how to write a prompt. How to build small tools of his own, with AI doing most of the typing.

His reaction near the end was that it meant "somebody like me can do some pretty amazing things."

That is a different goal from a company-wide session, and it is the right goal for one specific person: the founder or operator who will own systems day to day, and who needs to be able to open one and change it. For most staff, the aim is that they use what lands in their tools. For that one person, the aim is that they can make the next one.

How I plan training now

Train on the team's own work. Interview first, even briefly. If the examples could be used at any company, the session will be forgotten at every company.

Put a system behind it within weeks. Decide before the session which system will land inside that team's tools next, and when. Training creates an appetite. If nothing arrives to meet it, the appetite goes back to the old way of doing things.

Match the format to the job. Company-wide for a shared default and a shared vocabulary. A team session for a function whose systems are on the way. One-to-one for the person who will build and own.

Ask a month later, not at the end. The feedback form on the day measures the presenter. The question that matters is what people are using four weeks later, and the way to find out is to ask someone who would know. That is how I heard about the skincare company.

If you are booking a training this quarter, write one line before you sign: the name of the system that will land in that team's tools within thirty days, and the date it lands. If you cannot write that line yet, move the training until you can.