Onboarding AI

When I sit down to solve a problem with a colleague, I don’t come with all the answers. It’s why I’m not just doing it myself: my coworker can bring to bear her unique experience and skills.

I might start by stating the problem to solve, and a few constraints. Then I’d share how I’ve thought about the problem.

But before we get too far, I’d ask her opinion. She may see something I’ve missed, or have insights or experience I lack.

Together, we’d work out the right approach before anyone gets started in earnest.

But that wasn’t how I used AI at first.

I gave it an assignment — I need a slide deck formatted just so — waited for an answer, and spent time fruitlessly arguing with it when the output inevitably wasn’t quite right.

Then my friend John gave me a better mental model:

Think of AI as a brilliant junior colleague. It’s a fast worker who knows an enormous amount, but it’s new to your field, your organization, and the kind of work you’re trying to do.

That changed how I approach AI.

I stopped treating it as a drone to execute tasks and started treating it as a collaborator.

So I’m less likely to ask for a finished product and more likely to begin with the problem: Here’s what I’m trying to accomplish. Here’s how I see it. What questions do you have? How would you approach this?

The conversation that follows is often where the work gets better. AI can surface ambiguities I hadn’t noticed, suggest approaches I hadn’t considered, or help me make sense of a half-formed idea.

When my AI collaborators make suggestions, I use my judgment about whether and how to apply them. Sometimes they merely show me what not to do — which points towards a better answer.

This is possible because of a continuous process of learning — essentially onboarding a new colleague.

At work, I started by feeding it all our marketing frameworks, legal guidelines, style guides, examples of content that had actually landed well, and details about who else is involved.

On a regular basis I share examples of what’s working and what’s not from what we produce together. We’re constantly refining processes together to make things smoother or address gaps.

I still argue with it plenty. But it’s more constructive now.