Ep. 22: Continuing the AI Conversation - Part 1 (w. Cindy)

EPISODE DESCRIPTION

Artificial intelligence isn’t coming—it’s already changing the way we learn, work, and make decisions. In Part 1 of this two-part conversation, Cindy returns to the show as we unpack one of AI’s biggest impacts so far: education.

From students using ChatGPT to complete assignments to universities rethinking what learning even looks like, we explore the opportunities, challenges, and unintended consequences of AI in the classroom. We also discuss whether today’s students are actually being prepared for an AI-powered future—and whether schools are adapting quickly enough.

Rather than asking whether AI should be part of education, we ask a more important question: Now that it’s here, how do we use it well?

Referenced in this Episode

• CBS Chicago: UChicago curbing AI usage by banning technology in class for first-year law students
  https://www.youtube.com/watch?v=ejIxTTLsgzw

• The Wall Street Journal: High-Earner Families Are Ditching Traditional Schools for Life Skills and AI
  https://www.wsj.com/us-news/education/alternative-education-wealthy-families-ai-cd7922b3

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TRANSCRIPT

Matti: Cindy, welcome back.

Cindy: Thanks for having me again.

Matti: Before we get into AI, I have to ask. You live in New York. Were you at Taylor Swift’s wedding? Based on the guest list, it seemed like everyone else was.

Cindy: Absolutely. I was a bridesmaid.

Matti: Naturally.

Cindy: Well…everyone was there except Blake Lively.

Matti: I was looking through the photos thinking, How do all of these people know each other? Hugh Grant? George Stephanopoulos? At what point do those worlds collide?

Cindy: Maybe George delivered her pizza one night and they became lifelong friends. Honestly, that’s as plausible as anything else.

Matti: Fair enough. I figured you probably signed a non-disclosure agreement, so we’ll move on.

Law School Hits the Brakes on AI

Matti: One story that really caught my attention came out of the University of Chicago Law School. Incoming first-year law students are no longer allowed to bring laptops into class. No computers, no recording devices—just pen and paper. The goal is to eliminate AI shortcuts and force students to develop critical thinking skills before technology enters the equation.

When I first read it, I thought, This feels incredibly strange in 2026. Telling graduate students they can’t even bring a laptop into class seems almost backwards.

Cindy: It feels strange…and I kind of love it.

There are obviously situations where students need technology for accessibility, and I’d hope those accommodations remain available. But beyond that, I’m a fan. There are studies showing that people remember information better when they physically write notes rather than type them. Writing engages your brain differently.

I also remember being in college and constantly getting distracted by the person sitting in front of me who was supposedly taking notes but was actually playing online poker or browsing the internet. It’s amazing how much someone else’s laptop can pull your attention away from what’s happening in class.

I actually taught a college course a few years ago, and I had students who would spend entire lectures doing completely unrelated things on their computers. One student would randomly laugh during class—not because of anything I said—and finally admitted he wasn’t paying attention at all.

At that point I wanted to ask, “Why are you even here?”

Presence Is Becoming a Skill

Cindy: I’ve started seeing something similar when I lead career workshops for college students over Zoom. Some students clearly have my presentation open in one window while they’re doing something completely different on another screen. You can tell they’re listening to music or watching something else because they’ll start moving along to a beat that doesn’t exist in my presentation.

Then, at the end, they’re always the ones asking, “Will we get a recording of this?”

My reaction is always, “So you can watch it during someone else’s class?”

There’s this growing assumption that everything will be recorded, uploaded, and available later. But if students know they’ll always have access to the slides or the recording, they stop feeling the need to actually be present.

That’s one reason I like the idea of handwritten notes. You can’t outsource attention.

Pushback Against AI

Matti: What’s interesting is that this feels like part of a broader trend. For years the conversation has been, “AI is faster. AI is smarter. AI is the future.” But recently I’ve started noticing pockets of resistance.

During graduation season, students actually booed commencement speakers who immediately pivoted into talking about AI.

Earlier today I met with a group of podcast consultants, and one thing they emphasized over and over was that while they may use AI to assist their workflow, they never allow AI to generate final creative work without human oversight. They were proud enough of that philosophy that it was included in their marketing materials.

I’m starting to see more organizations deliberately saying, “We’re going to use this carefully.”

Honestly, I find that encouraging. I don’t think friction is a bad thing. Sometimes it’s healthy for society to slow down before adopting every new technology without asking whether we should.

Cindy: I agree. The internet arrived and everyone immediately climbed aboard. Overall, I think that’s been a wonderful thing. We’re recording this podcast from different states because of technology.

But that doesn’t mean every technological advancement should automatically be integrated into every part of our lives without reflection.

Maybe this is simply society asking whether we moved too quickly.

Remember Word Processors?

Cindy: We also forget how recent all of this really is.

When I was in college, I rarely brought my laptop to class because it weighed about ten pounds. During my senior year it completely died, and I decided not to replace it because graduation was only a few months away. I simply used the university computer labs.

Everything worked out just fine.

Then I think about my older sister. When she went to college, she used a word processor—not even a computer, just a machine designed for typing papers. I remember thinking that someday I’d own one too.

Technology changes incredibly fast.

Which is probably why I still think about BlackBerrys more often than I’d like to admit.

Matti: You need to watch the BlackBerry movie.

Cindy: It’s been on my list forever. Every time I need a new phone, part of me wonders if I should just find an old BlackBerry instead.

Matti: What do you miss about it?

Cindy: The keyboard. The tactile feeling. It discouraged endless scrolling because the phone was designed to communicate—not to trap your attention.

I honestly miss that.

The AI School Experiment

Matti: While law schools seem to be pumping the brakes on AI, I came across another story that takes almost the exact opposite approach. The Wall Street Journal recently profiled a new K–8 school that’s built around AI-powered personalized learning. Instead of relying primarily on traditional classroom instruction, students spend part of their day learning through AI tutors that adapt lessons specifically to each child. The idea is that every student learns differently, and AI can supposedly personalize education in ways a teacher with twenty-five students simply can’t. There are some obvious selling points. Students can move at their own pace, spend more time on concepts they struggle with, and focus less on memorizing information and more on practical skills they’ll actually use later in life. But there are some significant drawbacks too. Tuition ranges from roughly $24,000 to more than $70,000 a year depending on the campus, the model is still largely unproven, and perhaps most importantly, it dramatically changes the role of teachers in the classroom.

Cindy: Before I answer, I have to ask a clarifying question. Is this a traditional school where teachers are using AI as another classroom tool, or are students essentially sitting in front of computers learning directly from AI?

Matti: Mostly the second one. There are still projects and activities with people, but AI is really at the center of the learning experience.

Cindy: Then I have to be honest—I hate almost everything about this. Before I even explain why, I think it’s interesting that there are schools moving in the exact opposite direction. Some elementary and middle schools are eliminating phones entirely because they’ve decided kids need less technology, not more. I’d love to see where those students are in twenty years compared to students whose education was built around AI. I also don’t really buy the basic premise that only AI can personalize learning. Yes, teachers have enormous classrooms. Yes, some struggle to reach every student equally. But great teachers have always personalized instruction. I had an incredible teacher growing up who knew exactly when I needed to be challenged and when I needed extra support. If I finished work early, he’d quietly hand me something more advanced. If I had an unusually bad day and bombed a test—which for me meant getting a B instead of my usual grade—he pulled me aside afterward and said, “I’m not counting this. Something’s clearly wrong. My door is open whenever you’re ready to talk.” He recognized that my performance wasn’t the problem. Something else was. That’s personalization, and it came from someone who actually knew me. I worry that instead of investing more in teachers and giving them the resources to do more of that, we’re deciding the solution is simply to replace them with software.

Learning Through Imperfection

Matti: That’s actually something I’ve been thinking about too. I wonder whether we’ve become so focused on creating the perfect educational experience that we’ve forgotten how much learning happens when things aren’t perfect. Sometimes you get a teacher whose style doesn’t click with yours. Sometimes you have to figure out how to succeed anyway. Later in life you’ll have difficult bosses, coworkers who communicate differently than you do, and situations that aren’t tailored to your preferences. Part of growing up is learning how to navigate those realities. Jonathan Haidt talks about this with children generally—that adults are often too quick to solve every conflict or remove every obstacle, when sometimes kids become more resilient by working through those situations themselves. Maybe education works the same way.

Cindy: I think that’s exactly right. I actually had a math teacher in high school who looked me in the eye after I asked a question and said, “Only a stupid person would ask that.” The room went completely silent. Other students came up to me afterward because they couldn’t believe she’d said it. I reported it to the school psychologist, who agreed it was inappropriate but also explained something I didn’t fully appreciate until years later. The teacher was retiring in a few months, and realistically there wasn’t going to be any formal discipline. Not because what happened was acceptable, but because institutions can’t always fix every problem. Looking back, that experience taught me something just as valuable as anything I learned in math class. It taught me that I could advocate for myself, that speaking up matters even when the outcome isn’t perfect, and that sometimes life simply isn’t fair. Those lessons are uncomfortable, but they’re real. I’m not sure an educational system that’s constantly optimizing every experience leaves much room for that kind of growth.

What Teachers See That AI Can’t

Cindy: The other thing that worries me is that teachers do so much more than deliver information. Kids build relationships with them. They notice when a student suddenly becomes withdrawn. They recognize changes in behavior. They’re mandated reporters if they suspect abuse or neglect. They’re often the first trusted adult outside the family who realizes something isn’t right. At the same time, we’re already seeing children treat AI assistants and chatbots almost like friends or therapists. Kids don’t understand digital privacy. They don’t understand what information is being collected or how permanent those conversations might become. Adults struggle with those questions. Expecting an eight-year-old to navigate them feels unrealistic. And beyond the privacy concerns, I worry about dependence. We’re already learning that many forms of technology are intentionally designed to keep people engaged. If we make AI the center of a child’s educational experience, are we also making it the center of how they think, solve problems, and seek reassurance? We simply don’t know enough yet to answer that.

Matti: Listening to you, I think you’ve landed on a distinction that makes a lot of sense. Maybe the question isn’t whether AI belongs in education. Maybe it’s who should be using it.

Cindy: Exactly. I would absolutely encourage teachers to use AI as a professional tool. Ask it for lesson plan ideas. Use it to brainstorm activities for visual learners. Have it suggest different ways to explain difficult concepts or make lessons more accessible. Those are all fantastic uses because the teacher remains the educator. AI is supporting the teacher—not replacing the relationship between teacher and student.

Matti: That’s an interesting way to think about it. We already accept that certain technologies require training or maturity before someone should use them. Maybe AI eventually fits into that category too. A trained professional using AI responsibly feels very different from asking a ten-year-old to build their education around it.

Relationships Can’t Be Automated

Cindy: That’s really where I keep coming back. Some of the most important things I learned in school had nothing to do with academics. I’m still best friends with someone because one of our teachers intervened when we were kids. We’d gotten into a ridiculous fight over a Koosh ball, and she kept us after class and basically said, “I’ve watched the two of you for years. You’re good friends. This argument isn’t worth losing that friendship.” She sat with us until we worked it out. I’m still friends with that person today. That’s what teachers do. They notice relationships. They understand context. They recognize when something matters more than finishing the day’s lesson. Maybe AI will continue improving, and maybe it will become an incredible educational tool. But I still think there are moments in a child’s development that require another human being sitting across from them.

Matti: I think that’s the perfect place to pause. Next week we’ll shift our conversation from AI in the classroom to AI in the workplace, where we’ll unpack a fascinating interview with the CEO of Levi’s and try to answer a question we kept asking ourselves while we watched it: What are companies actually saying when they talk about AI—and what are they leaving unsaid?

This transcript has been edited for readability.