Where AI Sits at the Education Table—Leaders Tell All

No Zoom. No laptops. Yes—actual people, real food, proper utensils. A rarity these days: humans, talking face to face about AI. That’s what Nick Mehta and Sandi Lin led for a much-needed Bay Area lunch meetup after the excitement of the Gainsight acquistion. 

And weirdly, that made all the difference. Less theory. More substance. I had the chance to sit down with a group of incredibly sharp folks working in customer education, enablement, and success—people knee-deep in the same big questions we’re all trying to answer. No slides. No agenda. Just conversation.

Now, this isn’t a “how-to” article. There’s no three-step plan or magic template here. It’s just me, telling the story of what I heard—and feeling like there’s no way I could not share it. (Shocking to think someone gets into content and then wants to, you know, actually write things down.)

So here it is: no names, no tools, no play-by-play. Just some of the ideas, questions, and very human moments that came up over lunch.

AI Won’t Drive Unless You Put the Right People in the Front Seat

We started with a classic prompt: What would you do with an unlimited budget for education?

You’d think the answers would be about scaling up tech or building a mini Hollywood studio. Some joked about retiring early or disappearing to an island. But what stuck? Nearly everyone said they’d invest in people. Not more people. The right ones.

Because here’s the thing: if you’ve got a dozen folks using AI in twelve different (and let’s be honest, sometimes questionable) ways, you’re not gaining much. If anything, you’re just speeding up confusion.

But when you’ve got a few smart humans in the mix—people who know how to drive, steer, and occasionally slam the brakes—AI actually becomes useful. That’s when things start to click. That’s when you move.

Your Title Says “Education.” Your Job Is Half the Company.

This part felt familiar to pretty much everyone at the table. CE leaders aren’t just running a learning platform. They’re doing onboarding. They’re writing help docs. They’re leading internal training. Sometimes they’re rewriting product messaging. And in more than a few cases, they’re now expected to feed content to AI agents, too.

One person described it as “the wild west,” and you could hear the chorus of agreement.

But it wasn’t all venting. What came through loud and clear was a quiet kind of ownership. This isn’t just scope creep—it’s a sign that education touches everything now. Whether or not it’s recognized on the org chart, these teams are already running the full learning ecosystem. They’re just doing it while holding everything else together, too.

What’s Actually Working (Even If It’s Not Always Polished)

Here’s the part that surprised me most. For all the talk about how overwhelming things are, people also shared what is working. Not “best practices.” Actual, gritty, in-progress wins.

Like training support bots to solve more real problems. Rewriting content to make it work better with AI systems—not just sound better to humans. Creating shared docs that multiple teams can pull from, instead of everyone starting from scratch.

Nobody claimed it was perfect. But it was progress. And it felt honest. These weren’t shiny case studies. They were scrappy solutions that happened because someone saw a gap and filled it.

People Still Don’t Want Your Features. They Want Help.

One topic kept resurfacing, like an uncomfortable but necessary truth: a lot of content just doesn’t land.

Not because customers don’t care. But because we’re often talking at them instead of helping them do something.

The group called it out: long release notes, disconnected how-tos, feature updates that feel more like announcements than anything actionable. It’s not what people need.

What they do need? A way to get from point A to point B. Clarity. Context. A sense that you get their job—not just your own roadmap.

Training That Feels Nothing Like Training

Then came one of the more animated stretches: what learning should feel like.

Not dry. Not passive. Not another checklist in a sea of tabs.

Someone said they wanted training to feel like a video game—and it wasn’t a metaphor. They meant immersive, surprising, maybe even fun. And they weren’t alone.

The energy behind that idea was real. Not because gamification is new, but because expectations have changed. If your content doesn’t grab attention, learners are gone. They’ve got faster ways to get answers.

So CE leaders are getting serious about making training that actually feels good to use. Branded. Bold. Built like something that earns trust instead of asking for it.

We're In It—This Bridge Moment Between Now and What’s Next

If there was one unspoken theme throughout, it was this: everyone’s on a bridge. Between what education used to be and whatever this next version is becoming.

Right now, most teams are:

• Rewriting old systems
  
  
• Teaching internal teams how to talk about AI features
  
  
• Figuring out how to train machines and humans—without losing either one
  
  

No one had a clean blueprint. But they all had instincts. Questions. A willingness to keep building, even when the map runs out.

And Honestly, Let’s Have More Conversations Like This

The lunch ended, but the energy didn’t. The room was buzzing in that way only shared challenges and good ideas can create.

And maybe that’s the point of this whole thing. Not to offer answers, but to make space for this kind of conversation. Offstage. Offscreen. Where it’s okay to be unsure, and even better to be honest.

Because while AI might be helping shape the future of learning, it’s still people doing the hard, thoughtful, meaningful work of deciding what that future should be.

And when they get together to talk about it—you want a seat at that table.

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