Ep. 23: Continuing the AI Conversation - Part 2 (w. Cindy)

Written by Matti Shicker
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EPISODE DESCRIPTION

Artificial intelligence is no longer a future workplace issue—it’s a present one. But are companies actually explaining what they’re doing with AI, or are they hiding behind buzzwords?

In Part 2 of our AI conversation, Cindy returns as we shift our focus from the classroom to the workplace. Using an interview with Levi’s CEO as a starting point, we unpack how organizations are talking about AI, why so much of the conversation feels vague, and what employees are really worried about.

We also explore how AI is influencing hiring, productivity, and workplace expectations; discuss whether today’s young professionals are truly unprepared for work, or whether the workplace itself has fundamentally changed; and share a few unforgettable intern stories that remind us every generation has its learning curve.

Rather than asking whether AI will replace jobs, we examine a more practical question: How should organizations use AI in ways that actually help people instead of simply sounding innovative?

Referenced in this Episode

TRANSCRIPT

If you listened to last week’s episode, you know that Cindy and I spent a lot of time talking about AI in education: whether we’re moving too quickly, whether kids actually benefit from having AI personalize their learning, and whether there are some things technology simply can’t replace. This week, we’re taking that conversation into the workplace. And we started with a clip that, honestly, may be one of the best examples I’ve seen of how companies are currently talking about AI.

The clip was from the Today show, featuring the CEO of Levi’s discussing how the company is incorporating AI into its creative and design work. The interviewer asked whether AI was being embraced by the company’s creative teams. The CEO explained that Levi’s is a brand built around authenticity and craft, but that AI could be a tool to help its designers think more broadly, increase their capacity and creativity, and come up with the next idea. It sounded impressive. It also sounded like almost nothing.

Matti: I don’t know about you, but I heard nothing of value in that interview. It was very much, “I love AI because my chairman of the board told me I had to say I love AI.” And then there was this moment where the interviewer asked whether AI was something they were really focused on, and she basically said, “It is,” before immediately moving on. Then came the reassurance that it’s not going to replace anyone’s job. Just trust me on that one. Wink, wink. The whole thing felt like it perfectly captured what people are worried about when it comes to AI in the workplace.

Cindy: I actually hope that whoever is responsible for preserving our history saves that clip, because I’d love to see what people were saying about previous technological revolutions. Imagine if we had a similar corporate statement from the introduction of the assembly line. Everyone looks back now and says, “Of course, the assembly line was amazing. Look at everything it allowed us to manufacture.” But I’d love to know what happened to the jobs and what people were actually saying at the time. This Levi’s clip feels incredibly representative of this moment. The first thing I thought of when you sent it to me was a job I had at an entertainment marketing agency. We’d sometimes make capabilities decks or pitch decks, and because none of us actually came from traditional marketing backgrounds, we had a pretty healthy sense of humor about all the corporate marketing language. We’d joke about the slide where we’d put all the “marketing mumbo jumbo”—KPIs, goals, target audience, innovative, experimental, ROI, all the words that sound impressive but can sometimes mean absolutely nothing.

One day I suggested that we literally make the slide a word cloud with “mumbo jumbo” in the middle and all those buzzwords surrounding it. We didn’t actually do it because, you know, we wanted to keep our jobs, but it was tempting. And that’s basically how this Levi’s interview felt to me. “It’s a tool.” “It’s about innovation.” “It’s about authenticity.” “It’s about craft.” Okay—but what is the tool actually doing? What problem is it solving? Are you using AI to make a production process more efficient? Are you using it to analyze data that would have taken humans weeks to process? Are you solving a sizing problem? Are you creating something that your designers literally couldn’t have done before? Tell me something specific. Instead, we’re getting this vague language about creativity and authenticity, and it leaves me wondering whether the company actually knows what it’s doing with AI or whether somebody simply told the CEO that she needed to have an AI answer ready.

Matti: And that’s what I think is important here. I’m not even criticizing her specifically. She’s the CEO of Levi’s. Great. She’s successful. But I think the interview is representative of a much bigger problem: companies don’t necessarily know how to talk about AI yet. They don’t know how to explain what they’re doing with it to their employees, their customers, or even investors in a way that actually means something. It almost reminded me of the old concept of “branded content” in magazines and newspapers. You’d have something that looked like an article but was really an advertisement designed to make the company look good. This felt like Levi’s saying, “We’d like to be part of the conversation about AI,” and the Today show giving them a platform to do that. But when you actually listen to the answer, there’s not much there.

And if you look at the comments on the video, people had essentially the same reaction we did. When I sent Cindy the clip, she responded, “I don’t fully understand what she’s saying beyond buzzwords.” Exactly. That’s what I heard too.

Cindy: Right. I think she was using a bunch of buzzwords designed to make shareholders think Levi’s is innovative and to make people who want Levi’s to be cool think they’re at the cutting edge of technology. And maybe that’s what they’re trying to accomplish. Levi’s has always had this very established identity—rugged, classic, your grandparents wore them, you’ll wear them too. Maybe they want to say, “We’re also the cool technology company now.” But I kept thinking about an old Levi’s commercial instead. Do you remember the Karma Chameleon karaoke commercial from the early 2000s?

Matti: Yes.

Cindy: That commercial actually made me want Levi’s. You had all these different people singing “Karma Chameleon” at karaoke, all wearing Levi’s, and they were completely different people. That felt like an actual creative idea. It communicated something about the brand. Compare that with “AI is about authenticity and craft.” You could say that about literally anything. It’s not telling me anything.

And here’s the thing: AI is already changing jobs. So when a CEO says, “It’s not about replacing people; it’s just a tool,” I want to know what that actually means. If AI lets one person do the work that previously required two people, technically AI didn’t “replace” a job. The company simply doesn’t need to hire that second person anymore. That’s still a change in employment. And maybe sometimes that’s okay! Companies overhire. Businesses need to become more efficient. Technology has always changed the way people work. But let’s be honest about what’s happening instead of hiding behind words like “innovation” and “capacity.”

The Jobs Question

Cindy then brought up a statistic she’d recently seen in Media War & Peace, a newsletter written by media analyst Evan Shapiro. The numbers weren’t specifically attributed to AI, but they were striking: in the first half of 2025, there were roughly 80,966 job losses across the media, entertainment, and technology sectors. In the first half of 2026, that number had risen to approximately 142,644. Since 2022, the total number of job losses across those sectors had surpassed one million. There are obviously many reasons for those layoffs, and it would be irresponsible to attribute all of them to AI. But the broader trend is impossible to ignore.

Matti: And that’s an important distinction. Those numbers aren’t saying AI caused all of those job losses. There are lots of factors. But there’s another way AI can affect employment even before it actually replaces someone’s job. Companies are already thinking about what AI might be able to do in the future. If a company expects technology to make certain jobs more efficient, it may decide not to replace someone who leaves. It may reduce hiring. It may restructure a department. So even if you can’t point to one specific person and say, “AI took that person’s job,” the expectation of what AI can eventually do is already changing how companies make decisions.

Cindy: Exactly. And if there’s a tool that can eliminate a middleman or make something significantly faster, that’s going to affect staffing too. Maybe something that used to require two people can now be done by one person with an AI tool. Again, maybe that’s good. Maybe it’s necessary. Maybe it’s just the natural evolution of work. But I’d love to check back in a year and see what Levi’s is actually doing. Did they hire more people? Did they lay people off? What exactly did those designers do with AI? Because if we’re going to talk about how AI is transforming the workplace, I’d rather hear the actual use case than a collection of buzzwords.

Matti: Mark your calendar. July 2027.

Cindy: I’ll be back.

And that’s really the question I kept coming back to throughout this whole conversation: What are companies actually doing with AI? If Levi’s had said, “Here’s a problem we’ve had for years. Here’s what our designers tried to do. Here’s where AI helped. Here’s what humans still had to do. And here’s the result,” I’d be interested. Maybe even excited. But when the answer is simply “innovation, authenticity, craft, creativity,” it feels less like an explanation and more like corporate fog.

And that fog becomes especially interesting when we start talking about the people who are already entering the workplace. Because while companies are trying to figure out how AI is going to change work, there’s a whole generation being told that they aren’t prepared for the workplace in the first place.

What Workplace Are We Talking About?

Matti: There was one other thing I wanted to talk about when it comes to AI and the workplace. I saw this Wall Street Journal article called “A New Lost Generation: Why Gen Z Is Unprepared for the Workplace.” It talked about how young workers supposedly don’t know how to handle conflict face-to-face, navigate social dynamics, read the room, or ask for feedback. And I read the entire 1,100-word article and had a two-word reaction: What workplace?

Because there isn’t really one universal workplace anymore. Every company is different. Some are hybrid, some are fully remote, some are back in the office five days a week. And ever since COVID, the way people interact at work has fundamentally changed. You have people who come into the office, sit with their teams, do their jobs, and leave. The whole idea of the workplace as this social environment where you make lifelong friends and learn how to navigate office politics just feels very different from what it was twenty or thirty years ago. The article seemed to be talking about the workplace like it was 1998, when everyone showed up at the same office every day and learned professional behavior by watching the people around them.

Cindy: I think it’s a little bit of a yes-and. On the one hand, I completely agree with you: what workplace are we talking about? I remember listening to a podcast about making the workplace more equitable, and one of the things they talked about was increasing schedule flexibility and remote work. That’s great for some people, but teaching is an on-site job. Are we saying that people who need flexibility shouldn’t be teachers? There are different dynamics at play, and there can’t be one universal answer.

I also think there’s a lot of generational politics that get wrapped into these conversations. Millennials are going to ruin the workplace. Gen Z is going to ruin the workplace. Every generation apparently arrives and destroys everything that came before it. And, by the way, millennials are old now. No offense to us, but we’re old. So I think some of this is just a recurring cycle that generates clicks.

But I do think there are some things worth taking seriously. There was a period during COVID when kids had to do school remotely, and depending on where they were in their education and how much remote schooling they experienced, there may have been some developmental gaps. I’m not taking a position on whether lockdowns were good or bad because I’m not a public health official, but I have noticed some differences in the college students and early-career professionals I work with. Sometimes recent graduates seem a little bit more like the sophomores of previous generations in terms of how they navigate certain situations. There are researchers studying this, and there are a lot of factors involved, but I think it’s worth acknowledging that something happened.

One of those things is communication. A university once asked me to teach a workshop about how to succeed in internships because several internship supervisors had complained that they couldn’t communicate properly with their students. The university was hearing the same complaint enough that they decided there was a real problem. Part of it was that students weren’t using email the same way previous generations had. Part of it was professional norms. And part of it was simply that nobody had ever taught them some of these things.

Matti: Right. And that’s the thing. I remember actually being taught how to write professional letters and emails. There was an expectation that you would know how to communicate professionally before you entered the workplace. That’s not necessarily happening for everyone anymore.

Cindy: Exactly. And some of it is just that the modes of communication have changed. There are jokes about Gen Z not knowing how to use a phone or leave a voicemail, but that’s not entirely new. There was a Hills clip years ago where Stephanie Pratt was working at an internship and basically picked up the phone and immediately put it back down because she didn’t know what to do. She wasn’t Gen Z. So there are some things that are just part of being young and entering a workplace.

Dress is another one. Every generation has to learn what’s appropriate in a particular environment. When I was 19, I bought a sweater halter top from the professional section of the Gap and thought, “Well, it’s in the professional section, so obviously it’s professional.” All my friends got one for their internships. Looking back now, I have to say: what were we doing? Sometimes I still feel shame about wearing a halter top to work 20 years ago.

Matti: But it was cable knit.

Cindy: It was cable knit. That does not make it okay.

And that’s where you learn by watching people. If you’re working in person, you see what everyone else is wearing. You see how people communicate. You hear how they talk to their boss. You watch how someone handles a disagreement. Eventually you pick up on those norms. Maybe someone even pulls you aside and says, “Hey, we don’t wear mini skirts here, even if they are technically sold in the professional section.” That’s how professional culture gets transmitted. If you’ve only ever had remote internships and your first jobs are remote, you may not have had the opportunity to absorb those things through observation.

Matti: I remember something similar happening to me at my first job in Los Angeles. It was an advertising agency, so the dress code was extremely casual. Everyone wore jeans every day. We were going out to lunch with a vendor, so I wore jeans. Afterward, my boss came up to me and said, “Totally fine to wear jeans. Not fine when we’re going out to meet a vendor outside the office.” And I remember being so embarrassed. But it was actually good that she told me. I didn’t know. Someone had to explain it.

Cindy: Exactly. And people don’t necessarily give that feedback anymore. It works both ways, too. If you’ve only ever worked remotely, you may not know the rules for remote work. So this isn’t exclusively a Gen Z problem. It’s a professional-development problem.

Maybe the Problem Isn’t Gen Z

Matti: And that gets back to something we were talking about earlier with education: maybe not everything has to be optimized for you. If young workers are struggling with workplace norms, maybe the answer isn’t just to complain that they’re unprepared. Maybe employers need to actually teach them.

If you’re an employer and you’re frustrated because a young employee is using their phone to take notes, tell them what you expect. If you’re frustrated because someone doesn’t know how to write a professional email, teach them. If you’re frustrated because someone doesn’t understand how to interact with clients, give them feedback. Don’t assume that there’s some universal workplace code that everyone should magically know.

Cindy: Give feedback. In fact, I saw another statistic in that same newsletter I’d mentioned earlier that really jumped out at me. It looked at the average number of hours of formal employee development training per year. In 2020, it was around 35 hours per employee. In 2026, it was down to about 11.7 hours. That’s a massive reduction.

And then we’re surprised that people don’t know how to behave professionally? Sometimes we blame the age gap when the bigger issue might be that we’re not actually training people anymore.

Imagine I decided tomorrow that I’m going to become a phlebotomist. I don’t know how to behave in a lab. I don’t know how to sort needles. I don’t know what the workflow is. I don’t know anything about bedside manner beyond my own intuition. I would need training. And I’d probably have to learn the culture of whatever clinic or hospital hired me. If I went to a different clinic, some of those things would carry over and some wouldn’t. That’s just what it means to enter a new professional environment.

So if someone is young, we shouldn’t automatically assume that their age is the problem. Sometimes they’re just new.

Matti: And that’s exactly why I liked your point earlier about not having everything handed to you. You learn from the lack of optimization. You learn because you make a mistake. You learn because someone corrects you. You learn because you watch someone else handle something better than you did.

Cindy: I love that.

The Intern Hall of Fame

Matti: So that brings us perfectly to our last segment, which is a little more lighthearted. There’s a blog called Wall Street 360, and because it’s summer, it’s intern season. They posted a collection of funny stories about things interns have done, and I picked my top five because I wanted to hear your reaction as someone who works with Gen Z and spends a lot of time working with universities and early-career professionals.

First: “I got asked by the MBA associate intern if I started my internship on Monday, too. I said, ‘No, I’m a VP.’”

Cindy: That’s very cute.

Matti: I read that and thought, “Millennials look great.” We do look young.

Cindy: We made Botox a thing, so now nobody can tell.

Matti: Number two: “Emailed my managing director, ‘Sorry, what does ETA stand for?’”

Cindy: Honestly, that’s one where I think you can farm it out to AI. But good. There are so many of these little acronyms that I didn’t know either. TBD, EOD—how many times have I had to Google what some corporate acronym means?

Matti: And even when you know EOD means “end of day,” what exactly does that mean? Five o’clock? Six? Midnight? Eight fifty-nine the next morning?

Cindy: Nobody agrees! And sometimes I throw these acronyms into emails knowing that someone might not understand them and will have to Google them.

Matti: Number three: “I told my intern to lock his computer. He pulled out a padlock and chain.”

Cindy: That’s amazing.

Matti: I have to assume he brought it from home the next day, because if he just happened to have a padlock and chain in his backpack, that’s a whole other story.

Number four: “Wore a suit to Casual Friday. Told them to dress more casually. Wore a green neon T-shirt and sweats the next Friday.”

Cindy: Listen to the instructions in my book. He took the feedback!

Matti: He really did. He went from one extreme to the other.

Cindy: Gen Z can take feedback.

Matti: And finally: “Emailed the client a list of thoughts on day one.”

Cindy: No. That’s a thing that’s getting worse. I don’t like that.

But I’ll share one of my own. I had an intern who was sitting at her desk with a bowl in front of her and was literally drinking out of it. We turned around and said, “What’s going on?” And she said, “Well, I couldn’t find any cups and I got thirsty.” Instead of solving the problem by looking for a cup or asking someone where the cups were, she just decided, “I’m going to drink like a cat.”

Matti: That’s incredible.

Cindy: It’s my favorite story. I get a lot of mileage out of it.

Matti: I love that.

Cindy: She’s probably fine.

So… Is It Gonna Be Fine?

Matti: And that’s probably the right place to wrap this up. When we started this two-part conversation, we weren’t sure whether AI in education or AI in the workplace was going to leave us feeling particularly optimistic. And I don’t think we’re necessarily there yet. But there are some glimmers of hope.

Cindy: Not everyone is going at full speed. That’s important.

Matti: Exactly. There is pushback. There are people putting up checks and balances. There are schools taking technology away rather than adding more of it. There are workplaces trying to figure out what AI actually does instead of simply putting the word “AI” into every corporate presentation. And, importantly, we’re having conversations about all of this.

Cindy: I hope other people are too. I think it will be fine. Some of the kids in those $75,000-a-year AI schools? They’re not going to be fine yet. They’re not going to be fine.

Matti: Right. Well, the show’s called It’s Gonna Be Fine, not They’re Gonna Be Fine, so we’re good.

Cindy: Exactly.

Matti: Cindy, thank you so much. I will see you soon.

Cindy: Love you more than anything.

Matti: And to all the listeners, I love you too. We’ll see you next time.

Cindy: Bye.

This transcript has been edited for readability.

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