Where AI Andy Ends and the Real Work Begins

Lessons leaned from exporting my personality traits to AI

This past week, I invited people to engage with AI Andy—a digital experiment in capturing some of the ways I work with people, only this time filtered through the lens of artificial intelligence. The responses were powerful. I was honestly moved by how many of you took time to reflect, to share, and to open up. Thank you.

But something interesting happened. As I read through the messages, I started to notice a pattern. People often began with genuine curiosity and openness. But then—when the questions hit a nerve, or when the answers began brushing up against discomfort—some would shift. They’d make a joke. Skip ahead. Deflect. And the AI, by design, would let them. It would move on. It’s programmed to be helpful and safe, not to disrupt or hold someone in discomfort. It doesn’t sense the silence between words, or the hesitation in your fingertips as you type. It doesn’t ask again with the weight of presence behind it.

One moment stood out.

A close friend of mine wrote in, engaging with the AI around his depression. At first, the exchange was thoughtful and honest. But as the questions began to deepen—nudging toward territory that felt vulnerable—he started poking fun at the system. He mocked its tone. He joked about the structure of the questions. And just like that, the opportunity for something meaningful got diffused. Not because the AI failed, but because it didn’t know how to stay. It couldn’t say, “I see you are avoiding.”

That’s where the real work lives.

The value of a trainer, a guide, a coach, or any kind of human facilitator isn't just in asking good questions. It’s in knowing when someone is dancing around something important—and having the skill to bring them back to it. Gently, respectfully, but with purpose. There’s a real art to knowing when to push, when to wait, when to hold silence, and when to break it. It’s the ability to sense the edge of someone’s growth and help them lean into it without pushing them over.

AI can offer insights. It can be a mirror, a prompt, a starting place. But it can’t hold discomfort. It can’t create a container. It doesn’t know when something isn’t being said—and it can’t say, “Let’s not move on just yet.” At least not at the moment.

The work we do with each other, face-to-face or voice-to-voice, still matters deeply. Not because AI isn’t useful—it is. But because real transformation happens at the edge of our patterns, and that edge is where human presence still makes all the difference.

So while I’m incredibly grateful for what this experiment revealed, and there is still a whole lot more to come. I’m even more grateful for the reminder: it’s not just about what we say. It’s about how we stay.