Ask the Humans

There's a question that changes everything about AI adoption and it has nothing to do with AI.

I was on a podcast recently, AI Literacy for Entrepreneurs with Susan Diaz (who is absolutely brilliant), and we were deep in a conversation about workplace AI adoption when I said something that hit a nerve.

“What would make Monday easier for you?”

That's the question I believe every leader should ask their people before they push their AI agenda another inch forward.

And yet… most organizations rolling out AI right now have never asked it. Not once. They’ve bought the licences, booked the training, and written the comms plan. They’ve benchmarked the tools and built the business case. They may have even sat around the executive table and assumed they know what their people need, but they haven’t sat down with the actual humans doing the actual work and asked: what’s the part of your week that makes you want to crawl back under the covers?

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Easy Vs Easier

No change is ever 100% easy. But it can be easier. And that distinction matters more than most transformation plans ever acknowledge.

The longer I whirl around in this AI tornado, the more convinced I am of this: a person’s mindset about AI is either their ceiling or their sky.

When you ask someone what would make Monday easier, you’re not asking them about the big bad AI machine. You’re asking them about their life. Their inbox at 8am. The report they rebuild from scratch every week because no one ever fixed the template. The meeting that spawned three more meetings. The thing they dread. The thing that quietly drains them before lunch.

You’re asking them to name the friction in their day. And that friction? That’s your real AI adoption entry point.

So why do we keep bypassing the humans?

Because leadership is panicking and pushing AI. The project team is panicking and trying to hit the metrics. The change management team is panicking because everyone keeps forgetting there is a human in the loop. And humans are complicated.

And very few people in a big transformation want to say out loud what I’m going to say right now:

AI transformation is different than every transformation that came before it.

It’s not a startup. It’s not an IT rollout. It’s not a tool deployment with a go-live date and a hypercare period. It’s a fundamental shift in how humans relate to their own thinking. Their own value. Their own identity at work.

Treating it like a software upgrade is like treating grief as a scheduling problem.

The technology is the easy part. The humans are going to be the work.

And we’re going to slide up and down the emotional side of this change curve for quite some time.

(Personally, I think my change curve is a circle. With every new AI press release, I’m back in shock, and around we go again. Weeee!)

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So when you skip the Monday question, when you go straight to prompt libraries and lunch-and-learns and Copilot feature demos, you’re not just missing a step. You’re missing the whole point.

People don’t resist AI because they don’t understand it. They resist it because nobody’s made it relevant for them… yet. And if the organization shoves it down their throat before they’ve had space to figure out how it could actually solve the thing they’ve been dreading every Tuesday afternoon for the last year… you’ve lost them.

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So here’s what I want you to do.

If you’re leading AI in your organization or trying to get your team on board and getting eye rolls, try this before you build another training module.

Ask: What would make your Monday easier?

Then listen. Actually listen.

That answer is your roadmap. Adoption starts with what your people need, not what Silicon Valley promises.

I talked about this and a lot more with Susan on Episode 274 of AI Literacy for Entrepreneurs (Ps: there’s another cool project coming out of this podcast…it’ll be a first for me! Stay tuned.)