What kind of leadership prepares the next generation, and what kind of leadership makes them lose trust?

In this episode of TEXTing IRL, Elana Stein Hain and journalist Maya Sulkin mine Parashat Masei for competing models of leadership through a generation’s journey through the wilderness. Against the modern backdrop of AI, campus movements, and generational divides, they ask: Which of these models can still sustain a community? What would it mean to lead not by promising, controlling, or fighting, but by enabling people to grow?

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Are Today’s Leaders Failing Gen Z? Transcript

Note: This is a lightly edited transcript of a conversation, please excuse any errors.

Elana: Hello, everyone. Welcome back to TEXTing: Ideas for Real Life, where we wrestle with the big dilemmas of our time through the lens of classical and modern Torah texts. I’m your host, Elana Stein Hain. We’re recording on June 29th, 2026, and this episode is sponsored in honor of Robert Kogod’s 95th birthday by his loving family. Happy birthday. 

What kind of leadership is the next generation looking for? This answer will determine everything from the political realities to our communal boundaries. In an age suffused with the vitriol of the internet, the animation of AI technology, a retreat from earlier norms and institutions, who is going to shape the future of Jewish communities and the future of broader communities? And how? 

This week we end the Book of Numbers. It’s a perfect opportunity to look back on what exactly happened over a generation leaving Egypt, and a new generation winding its way to the Promised Land. The people who will enter the land are not those who were freed from Egypt, but actually their children and grandchildren.

I’m sitting here today with Maya Sulkin, whose reporting for the Free Press focuses on the ideological capture of university campuses and why young people are drawn to radical movements. She also writes about Gen Z and technology and how AI will shape her generation. Welcome, Maya. Thanks for being here. 

Maya: Thank you for having me. I’m honored to be here. 

Elana: Well, so I’m so excited to talk about this with you through the lens of leadership. It’s not just, what does the next generation want, but what kind of leaders do they need and what kind of leaders are they going to become? So the text I want to jump into is basically the rabbis trying to create a conversation across scripture. Because Parshat Masei, the final portion of Bamidbar, Parshat Masei, starts with eileh mas’ei b’nai yisrael, these are the journeys of the Jewish people and lists them. 

And in the Midrash the rabbis say, you know, we want to go to another verse elsewhere in the Bible into in Psalms, and basically ruminate on what it has meant for these people to be led through the wilderness, not just where have they been, but what have they gotten needed and turned their leadership into?

Okay, so the verse that they choose goes like this: nachita katzon amecha, you have guided—this word, nachita is going to become very important—you’ve guided like a flock your nation, beyad Moshe ve-Aharon, in the hands of Moses and Aaron. So what’s going to happen in this midrash is we’re going to take that word you have guided, and we’re going to basically turn it into a mnemonic for different ways of thinking about leadership.

But I want to start with you in terms of your experience and what you study, what you research, who you speak to. What do you make about the verse? What do you make about even the sheep and the flock metaphor, which is all over scripture, but I know has a lot of resonance with today’s rhetoric. 

Maya: Yeah, well, the first thing I would say that that kind of stands out is the sheet metaphor in the song that you read is not really about being passive. It’s about, kind of, having enough trust in in the shepherd, in the leader. Knowing your leader kind of knows the terrain. So I am very critical of Gen Z, but I would say the first thing I think of is less a critique of Gen Z and more critical of who is the shepherd that knows the terrain.

And the sheep metaphor is so interesting because now amongst young people, that’s kind of a dig. If you’re a sheep, that means you don’t think for yourself. You’re kind of part of the group thing. You, you know, are not willing to stand alone. But I think that what’s been lost is this idea that young people don’t know, or haven’t maybe been successfully convinced of, why it is important to be part of something bigger than yourself. And that requires actually a willingness to strip a little bit of your individuality. And we are so obsessed with our individuality that I think we lose out on being part of a flock or of being led. 

Elana: Okay, so let’s pause here for a second, because what you’re really pointing out is that the sheep metaphor has layers, right? Meaning one layer is basically you don’t know where you’re going. You’re just following whoever’s leading it. And that is definitely something that people speak about in a pejorative way today, right? 

But there’s another layer where you’re saying, it’s not that you don’t know where you’re going, it’s that you actually trust the person who is shepherding you, that they know where they’re going, and you actually think about who they are, and that determines whether you want to follow them, right? There’s a bit of critical thinking there. And then the third is collective, meaning, it’s actually important to belong to a flock. 

Now it’s interesting. Do you really think that Gen Z—let’s take like all three of these, right. The idea of blindly following, not thinking about the leadership, the concept of actually finding leaders you can trust the idea of being, not just about yourself, about others. You touched on the last one, but could we touch on the first two for a minute? Because you’re studying a lot of movements, right? Movement building. Don’t you find that sometimes in movement building, people are finding leaders who they trust? Or maybe they think they’re thinking for themselves and sometimes they’re not. Meaning, what do you find in there? What’s the texture?

Maya: Yeah. I think that anyone listening will think, but Gen Z are obsessed with being part of of movements!

Elana: Right. 

Maya: And that is true. My point is that I think they’re obsessed with being part of movements, and I’m speaking broadly and not about every single one, but I’m thinking specifically about what’s happening on campuses, for instance. You know, I think that what is drawing young people to those movements is less about what the movements actually stand for. It’s about a very human instinct to be want—to want to be part of a group. Like, we are not exempt from that. 

And so it’s why when you talk to young people on campuses, let’s say, about anti-Israel protests, and they don’t really know which river what you see, and you ask, okay. Why are you here? And they say, well, because my friends are here. And, you know, we know there are less frat parties, there are less like social institutions that young people are drawn to. And I think that’s why the social element is a really, really big part of this. I think about Covid, too. I don’t think that’s a coincidence.

Elana: So there’s kind of a reaction, you think? Meaning you’re—I have a split screen in my head, and then we’ll continue in the Midrash, but I have a split screen in my head. On the one hand, people want to be individuals. They don’t want to be thought of as sheep. But on the other hand, people really do want to belong. And sometimes that actually does lead them to just follow. 

By the way, whether they really understand the leader or they don’t understand the leader, whether they understand the issue or they don’t understand the issue. You could actually have both happening at the same time, which is a little bit strange, right? It’s a little bit surprising and maybe one is a reaction to the other.

Maya: And I think the sheep—and maybe that term in pop culture has been, has been changed and kind of meant something new in the last decade or so. But my point is kind of it, it, we crave being part of a flock and that is a good thing. It’s good to risk some individuality for being part of something bigger, but it requires pretty critical thinking about what am I sacrificing in the name of what as a means to what end? 

Elana: Got it. Well, one of the things that’s so funny, I wish I would have had you on for earlier portions in Bamidbar, because there were so many places where the Israelites are sort of like, okay, we’re thinking critically now, and Moses, we’re not sure we like you as our leader. We’re thinking critically now, Aaron. We’re not sure we like you as our leader, right? So it’s ,it’s interesting to look back at the book of Bamidbar in that way. 

So let’s see what some of the acronyms are that the rabbis play with because they’re really trying to reflect for us, almost like give us a, you know, like the canvas. What is it nachita? What does it mean that you led them? And of course, this verse is talking about God leading, but through Moses and Aaron.

Okay. So, nachita, you led. Rabbi Eliezer omer, Eliezer says, first, nissim, the n-n-n-n-n of nachita. Right? First, miracles asitah imahem, you did miracles for them. Second, the ch—chayim natatah lahem, you gave them life. Third, the y, yam karatah lahem, you tore the sea in half for them, the Reed Sea. And t—nachita—Torah natatah lahem. You gave them the Torah. You gave them teaching. Ve-al yedei mi? And through whom? Al yedei Moshe ve-Aharon. Through Moses and Aaron. 

And when I see this, I say to myself, if I were to ask myself, you know, what does leadership entail? There’s something here about elevating people by giving them something they don’t already have, right? That they might not have access to.

And in fact, that was Rabbi Eliezer. But Rabbi Yehoshua comes right after them, says something very similar. He says the n is for nifla’ot, wonders, and the ch is cherut, you gave them freedom, which they were slaves, right? The y is yemincha hoshiah otcham, your right hand saved them. And the t is tzlui rosh, you gave them basically the ability to raise their heads high.

Right? So I look at this and I say, I’m thinking about that kid in the driveway of The Incredibles movie. I don’t know if that’s, like, interesting to Gen Z, but I loved The Incredibles movie. And in The Incredibles movie, at some point, you have a little kid who’s just like sitting in the driveway of the super hero family, and the superhero dad goes, what are you waiting for? And, “something amazing!” like, he’s just waiting, right? So something about this leadership, giving you access to something amazing, something you don’t have on your own. What do you think about that?

Maya: Yeah. I think it’s kind of this, like, sacred promise in a way that’s like, if you follow me and you give up a little bit of yourself to something bigger, I will provide for you things you would not attain on your own. And that promise is really sacred. And I think people can wrap their heads around that in a really easy way. 

But when you kind of transition that into modern times, I won’t get too ahead of ourselves. That kind of starts to fall away a little bit. 

Elana: No, no, now you got me. Tell me, how does that start to fall away?

Maya: I think that when we talk about young people being very opposed or misguided or distrustful of institutions, I think it’s exactly what we’re reading now. It’s basically saying we were told that if we work hard in school, that if we major in X, Y, Z thing, if we get a certain degree, we’ll have lives. Maybe even like our parents we’ll be successful. We will be able to have kids, buy a home, send our own kids to college. And I think what you’re seeing happening is that we held on to those. That promise basically as like a universal truth. 

And now it’s basically saying, wait, the things I was promised that I wouldn’t have been able to attain on my own. I’m not getting the return. So now I’ve done all this work, you know, maybe I’ve taken out student loans, and I can’t get a job. I don’t think I’ll ever be able to buy a home. And so this sacred promise has kind of fallen away a little bit. 

And I think about AI, it’s kind of the obvious force behind all of this, which is that if all of the things that I was working toward that kind of made me uniquely human or showed that I had some value, whether it was passing the bar exam or writing an essay on Tolstoy, if an LLM can do all of those things, what am I really here for? And I don’t think institutions are showing people or are, you know, have the shepherds in place to show young people. Well, this is why you do those things. 

Elana: What do you think, just talking about, like fixing the plane as we fly it. Do you think the leadership knows the answer to that? 

Maya: No, of course not. And I think there is like some humility required that’s not totally there. And so—

Elana: Meaning, on behalf of leadership. Meaning, on behalf of people who are continuing the systems as they were, okay, so you want to see humility. What does that look like? 

Maya: Well, you know, you read all these stories about professors. I mean, this is a whole other subject. And like, I’m pretty much very opposed to AI in school. But you read stories of these professors basically giving kids zeros because they can tell they used AI in their essays. And I actually have some sympathy for these kids because they’re saying, well, easy for you to say. You have tenure. And this system worked perfectly for you. You went to college, you got your degree, you got the job you were promised, you know, by virtue of kind of going through those, those those, you know, programs. 

And now this whole new thing is here, and you’re telling me how I can or can’t use it. But the thing is, it’s all kind of a fake premise, because in the real world, that’s not how it’s going.

Elana: You need it in order to succeed. And even as you’re using it, it’s making you feel less than. 

Maya: Yeah. So if we talk about kind of—exactly. Like, we all crave things that will elevate us, but the things that made that possible before education, institutions, that’s all kind of been ruptured by AI in large part. 

Elana: Wow. 

Maya: Ben Sasse, the former University of Florida president who has terminal cancer and has been speaking out a lot in this, like, final months of life, basically said, like, AI will bring us heaven and it will bring us hell, and it will be hell for the people that outsource all of their thinking and affections to it. And so how do you cultivate a generation that understands what this tool is for, but does not lose the sense that what makes them valuable and human is still important? And what are the leaders doing to help guide young people, to say, this is what makes you human, and this is how you know, these promises can maybe look different but still remain intact. 

Elana: Well, so it’s a it’s a very good segue to the next part of the Midrash, because the next part of the Midrash does not take this approach of, there’s something that we have access to, and we’re going to, you know, hold out this promise and you will have access to it, too, right? This is a much more—focusing on how to build the people up themselves and have them create themselves. 

And it goes like this: ve-rabboteinu omrim, the rabbis say, which is different than saying Rabbi Eliezer says this or Rabbi Yehoshua says this. It sounds like this is an agreed upon approach by a number of different thinkers. Nechita, you have led, the nun, the n is for nev’im he’emadeta meihem, you brought out prophets from among the people. Chasidim he’emadeta meihem, you brought out pious people from among the people. Yesharim he’emadeta meihem, you brought out upright people from among the flock, right? Tmemim he’emadeta meihem, you brought out—I mean, literally it means perfect ones, right? But faultless ones from among them. 

Al yedei Moshe ve-Aharon, through Moses and Aaron, meaning Moses and Aaron are not the perfect ones, the prophets, Capital T, capital H, capital E right. It’s—you have to figure out a way to get them to actually achieve, like, Maslow’s hierarchy, have them climbing that, not with something that you’re holding out, that you, that may or may not work, but somehow grass-roots it somehow. And I’m curious what you think. 

Maya: Well, to me, the text is basically saying the job of the leader is not to be the faultless one, but to cultivate the next generation. It is their job to, kind of, among the flock, cultivate people, to kind of pass the torch to. And so that is perhaps the most important job of a leader.  

When you think about young people and their distaste for institutions, or they’re kind of the only way I know how to put it is like the norms that have kind of fallen away about what’s evil, what’s right, what’s wrong. I think it’s in part while you see young people moving a little bit towards faith, I think about even watching and I’m not saying this in a political sense, but if you think about, you know, Joe Biden running for president and you had all of these young people basically saying, isn’t it your job to pass the torch to find someone that you think is the best fit to kind of lead this group of people? You could kind of carry this metaphor out through, through a number of groups. 

Elana: Oh my gosh, it’s fascinating. It’s fascinating because actually, when you think about our past presidential election, it’s like, why are the people running for office so old? Like I—

Maya: Exactly.

Elana: It doesn’t—something doesn’t make sense. And then, by the way, I’m from New York, so I’m looking at what happened in the New York Democratic primaries. 

Maya: Exactly.

And guess who’s winning? Young people. 

Maya: Exactly.

Elana: We have a young new mayor, meaning I think there are people who are taking that on. But this is why I wanted to talk to you about this through leadership. Because yes, I think it’s true that the next generation will find its way because everybody finds their way. I think the question is, does leadership now want to actually be able to shape that in any way that will, I would say, prevent us from reaching pretty dangerous results in the future, right? Like prevent us from just rupture. 

Maya: Yeah, I think the case study of New York is such an interesting one because regardless of of his politics, what young people saw Mamdani was like a piece of themselves. They saw someone really frustrated with the existing system and trying to fix in ways they understood, even if that was TikTok videos, like, he spoke their language, and I think it made people feel really seen.

But broadly, no, I don’t see that kind of cultivation of, of young people, especially in the university, to kind of to kind of pass the torch on to. 

Elana: What would it look like? What would it look like? Like, let’s just dream for a minute. What would it look like to you? Because you interview many, many people in this generation. What would it look like to actually be passing that torch? 

Maya: Yeah, I think what—the first thing is that if we were dreaming, I would say a lot of the institutions that we look to right now, I don’t think have the kind of foundations and values that will sustain us for the next ten, 20, 30 years. So part of me thinks we kind of need to break things down and build them up again. 

Like we’re kind of naive to think that in, in the next 50, 100 years, a place like Columbia or Harvard will have the same weight that it did 50 or 100 years ago. So part of it is just saying these institutions do hold a different place for us. Okay. Knowing that, what are the what are the important roles that young people will need to play? Who are the people at the forefront? 

And I think a lot of it will be building new institutions that are kind of more awake to the current moment and what it demands of young people. Young people are really smart. So even the most nihilistic people that I, that I talked to, you know, I’ve spoken to young people who, when Sam Altman, the CEO of OpenAI, had a molotov cocktail thrown across his window. I spoke to young people who were in full support of that. And their reasoning for being supportive of that is because they’re saying, this is a person who is basically telling my entire generation that we will be jobless and we won’t—there’s no point for us here. And so it’s kind of this like violent, violent nihilism. 

But I think that the reason they’re drawn to those things is they’re just looking for someone to look at the reality of the situation and say, yeah, you’re right, this technology will change what it means for you to be human. But I’m here to tell you there’s this new vision. 

Elana: It’s so interesting I think because I see—I, maybe I’m like a, like the most glass half full pessimist I’ve ever met, but I think that I sometimes focus on those situations where you’re specifically trying to bring the next generation into the conversation by having all sorts of things, whether it’s hackathons or emphasizing those who are really doing. But what you’re saying is you got to make sure that the 90% of everyone else is actually getting in there. 

So let’s look at the end, because I see our time is coming to an end. But let’s look at the end of this midrash or the end of this section of the Midrash, because we have one more. Rabbi Akiva has his own take on it, okay? He says this nachita stands for nora’ot asita b’soneihem, you did wondrous things against those who are their enemies, and he sticks with this fighting enemies theme. He says the ch is charon af chalafta bahem, you sent your anger towards their enemies. The yud, the y, is yadcha kulchama otam, it was your hand waged war against their enemies. And the t, the taf is to to tehomot kisita aleihem. You covered over the enemies with the depth right, kind of an indication of the Egyptians going into the sea and being covered over by the water. Al yedei mi? By whom? Al yedei Moshe ve-Aharon, through Moses and Aaron. 

And I think this is a very, kind of militant view that I think views us as, whoa, we need protection. There is an enemy out there, and what our leaders are going to do is they are going to stand up against our enemies.

And I, as a non-specialist, but just as a human watching what’s happening, I feel that many people have identified who and what their enemies are, and their leaders are going to help get those enemies. They’re going to help undermine them. They’re going to fight them, they’re going to subdue them. Sometimes they’re even going to put them in jail, like, it’s on the left, the sense that we’ve got enemies and our leaders are going to fight them for us. Tell me about that and what the heck we should do about that. 

Maya: I was going to say, if we put all of these texts in front of a cohort of young people, I would say the one they would resonate most with is this one. And it’s because it is defined by having a clear enemy. And so because groups leaders have failed to properly show young people why you should be part of a group for positive reasons, they have then become part of groups because there is an enemy and that is enormously appealing to us. It’s why you see why all of these radical movements you pointed out, even online communities, it’s extremely dangerous. 

And this violence, like you said, is really attractive to young people. To me, it’s because everything for us is online and feels slightly intangible. And so this kind of extreme, violent nature feels so real when so much is really automated and not real. But I do think that, like what you’re saying, that being a part of a group because there is someone you are fighting against, is the value proposition for young people of why to belong to something. 

So what do we do? We have to show them a value proposition of being a part of something big and meaningful that is not inherently negative or fighting against something. And of course, every group has its values and standards, and in creating values and standards, you’re opposed to some other set of values and standards.

Elana: Sure.

Maya: But they should be optimistic ones rather than nihilistic ones, which I think is with so many young people are drawn to.

Elana: Yeah, it’s an interesting thing. You know, when we talk about fighting for something versus fighting against something, I think often about this time frame that we’re living in as a revolutionary time. And a revolutionary time is about overturning, over throwing something. Revolutionary times scare me very much. I think they become very violent in the name of morality, by the way. And I don’t want revolution on the right, and I don’t want a revolution on the left. I don’t want either of them.

So I think, tell me if you think this is fair, Maya, because I know we’re basically a time, it sounds like for this generation, the idea of looking at leadership as I’m going to give you something you don’t have access to, may not really work in this AI moment, because actually, the thing that leaders have that they don’t have access to, they may never have access to. 

And it sounds like this idea of I’m going to fight your enemies for you. Yes, it is alluring, but it’s very, very dangerous. It sounds like what? Like if you and I were actually saying to people like, What’s the Torah of leadership right now? I think we would say the middle one, which is try to help people actually make something of themselves, and that that’s really what we need in a time where people are not sure why they matter. Do you think that’s fair? In closing? 

Maya: Yes. And I think it’s so relevant because again, like we said at the beginning, the leaders aren’t entering the promised land. It is the young, it is their offspring, it is their children and their grandchildren. And so they actually, you know, the job now is saying what made this journey, this treacherous journey meaningful and worthwhile and what kind of people did it produce? 

And can those people sustain what their, their, you know, grandmothers and grandfathers worked so hard for? And so I think you’re right. It’s, it’s creating a new kind of way of looking at things that says, you know, here’s the glass half full of what makes what is the new promise and what is the value proposition for you? 

Elana: Right. And how do we make it real? Right? Meaning it’s—how do we make it not just a bill of goods. How do we really make it real? 

Well, Maya, thank you so much for joining me today and for giving me your perspective and for continuing to try to expose people to the perspectives of that generation through your writing and through your interviews. Thank you.

Maya: Thank you so much for having me.