Olivia: Alright Jackson, I'm going to say a phrase, and you tell me the first thing that comes to mind: "The Corporate Ladder." Jackson: Oh, easy. A rickety, wooden antique that leads to a dusty attic filled with forgotten dreams and bad coffee. Definitely not something you'd want to climb in 2024. Olivia: (Laughs) That is the perfect, if slightly cynical, image. And it’s exactly the premise behind the book we’re diving into today: Becoming the Boss: New Rules for the Next Generation of Leaders by Lindsey Pollak. Jackson: A book for those of us who see that ladder and think, "I'd rather take the elevator, or maybe just build a new building altogether." Olivia: Precisely. And Pollak is the perfect architect for that new building. She's a Yale grad and a leading expert on the multigenerational workforce. People call her a "generational translator," helping companies understand the massive shifts happening as millennials and Gen Z step into leadership. Jackson: A generational translator. I like that. It sounds much more useful than a corporate jargon translator, which I think is what most leadership books are. Olivia: It is. She argues that the old playbook for becoming a leader is not just outdated; it's fundamentally broken. The world has changed so dramatically that the very concept of "the boss" needs a complete reboot. Jackson: Okay, I'm intrigued. So where does this reboot begin? Do we just throw out everything our parents taught us about work? Olivia: In a way, yes. Pollak starts by showing us that the battlefield itself has changed. The old strategies don't work because we're not fighting the same war.

Jackson: "Battlefield," "war"... that sounds a little intense for a Tuesday morning meeting. What makes the modern workplace so different? Olivia: Pollak boils it down to three simultaneous revolutions: demographic, economic, and technological. And the scale of them is staggering. Let's start with the demographic one. You know how people talk about the "great retirement"? Jackson: Yeah, the Baby Boomers are finally hanging up their hats. Olivia: It’s more like a tidal wave. Pollak cites a PwC study that found 63 percent of American executives will be eligible to retire in the next five years. Jackson: Whoa. Sixty-three percent? That’s not a trickle, that’s a power vacuum. That's a kingdom without a king. Olivia: Exactly. And who's stepping in? Millennials. By 2020, they were projected to be 50 percent of the entire U.S. workforce. This isn't just a changing of the guard; it's a fundamental shift in the values, expectations, and communication styles that define a workplace. Jackson: Okay, that makes sense. But what about the economic revolution? Is that just about the rise of other countries? Olivia: That's part of it, with China and India's economies growing so rapidly. But it's also deeply personal, especially for the incoming leaders. Pollak drops this absolutely mind-blowing statistic: since 1978, college tuition fees in the U.S. have surged by 1,120 percent. Jackson: Hold on, say that again. One thousand, one hundred and twenty percent? That can't be real. That's not an increase; that's a statistical assault. Olivia: It’s real. And it’s more than triple the rate of inflation. So you have a generation of leaders stepping up who are saddled with unprecedented debt, facing higher costs of living, and entering what Pollak calls a "post-employment" economy, where companies can thrive without hiring as many people or paying them as well. The financial ground beneath their feet is completely different from their predecessors. Jackson: So they're being asked to lead while also just trying to stay afloat. That adds a layer of pressure that the old guard might not fully appreciate. Olivia: And then there's the third revolution: technology. Pollak tells this great story to illustrate the speed. It took landline telephones about 45 years to go from 5% to 50% penetration in U.S. households. Jackson: Okay, 45 years. Seems reasonable for a major infrastructure change. Olivia: Guess how long it took mobile phones to do the same. Jackson: I don't know... 15 years? 10? Olivia: Seven. Seven years. The pace of change is accelerating so fast that the skills you need to lead are in constant flux. You have to manage virtual teams, navigate the etiquette of new communication tools, and keep up with a relentless stream of new apps and platforms. Jackson: It feels like we're building the plane while flying it. But I have to ask, Olivia, when we talk about "millennials" or "boomers," isn't there a danger of oversimplifying? Of putting people into neat little boxes? Olivia: That’s a great point, and Pollak addresses it directly. She says these are not meant to be rigid stereotypes but broad cultural trends shaped by shared historical moments. She has this brilliant description of Generation X, the one sandwiched between the massive Boomer and Millennial generations. She quotes a Gen Xer who says, "Think of us as older siblings, resenting the fact that our younger siblings seem to have things so much easier and get so much more attention than we ever did." It’s a feeling of being overlooked. Jackson: The latchkey kids who raised themselves and then got skipped over. I can see that. So, if the entire landscape has changed—demographically, economically, technologically—then the old advice to just "work hard and climb the ladder" is basically useless. Olivia: It's worse than useless. It's a map to a world that no longer exists. And that's why Pollak argues the first step to becoming a boss today isn't about managing others. It's about managing yourself.

Jackson: Okay, so the world is on fire. The old maps are useless. What are we supposed to do about it? Just panic? Olivia: (Laughs) That's one option. But Pollak's answer is much more empowering. She says you can't wait for a company to define your career anymore. You have to become the CEO of 'You, Inc.' Jackson: The CEO of 'You, Inc.' I've heard that phrase before. It sounds a bit like corporate self-help speak. What does it actually mean in practice? Olivia: It means your professional reputation—your personal brand—is the single most important asset you manage. It's not about a title you're given; it's about the reputation you actively build, every single day. And it gets tested in the most unexpected ways. Pollak tells this incredible, and incredibly awkward, story. Jackson: Oh, I'm ready for this. Olivia: She's in her thirties, a successful business owner, at a professional conference. She's dressed in a suit, representing her company. An older man, maybe in his sixties or seventies, comes over from a neighboring booth to chat. They have a perfectly normal, professional conversation. Jackson: Okay, standard conference stuff. Olivia: As he's leaving, he says, "Nice to meet you." Then he reaches out, touches his fingertip to the end of her nose, and says, "Boop!" Jackson: (Bursts out laughing) No! He did not! A 'boop'? In a professional setting? That is a wild move. What did she do? Olivia: She was completely stunned, but she chose to just ignore it. He was much older, it wasn't aggressive, and she'd likely never see him again. But she uses it as a perfect example of how your leadership brand is constantly being challenged. In that moment, she had to decide: do I confront, deflect, or ignore? Each choice sends a different message about her brand. Jackson: That's fascinating. The 'boop' is a test. It's a bizarre, condescending test, but it's a test of her authority and how she carries herself. So how do you build a brand that can withstand a random 'boop'? Olivia: Pollak breaks it down into four key elements: Visibility, Differentiation, Consistency, and Authenticity. You have to be known for something unique, you have to deliver on it consistently, and it has to be genuinely you. Jackson: But what if you're just starting out? I don't have a 'brand.' I have a resume and a crippling fear of public speaking. How do you build a brand from scratch? Olivia: Pollak's advice is to start acting like a leader long before you have the title. It's in the small things. She talks about the importance of a confident handshake, of dressing one level up from your team to project authority, and of having a concise, powerful self-introduction ready at all times. It's about demonstrating leadership qualities in your daily actions. Jackson: So it's not about having a fancy logo for 'You, Inc.' It's about the product itself—how you show up, how you communicate, how you handle a 'boop.' Olivia: Exactly. And it’s about realizing that the line between your personal and professional life has basically evaporated. Lori High from The Hartford has this great quote in the book: "If you’re wise in your personal matters, people have so much more confidence that you are wise in your business matters... There is no longer a private world and public world." Jackson: That's a heavy thought. It means your brand is 'on' 24/7. But it makes sense. If you're building a brand, you can't just clock out. Olivia: You can't. And once you've started building that brand, the real work begins: leading other people. And that's where the new rules get even messier and more human.

Olivia: Building your brand is one thing, but leadership is ultimately about people. It's about influence and connection. Jackson: Right, especially connecting with people who aren't like you. How do you manage someone who remembers when your phone was attached to a wall with a curly cord? That's the real challenge for a young boss. Olivia: It's a huge one. A CareerBuilder survey found that 34% of U.S. workers say their boss is younger than they are. Pollak's first rule for managing older employees is simple but powerful: don't assume age is an issue. Jackson: That's easier said than done. It's got to feel awkward. Olivia: It can be. But she says you earn their respect by showing respect for their experience and institutional knowledge. You don't come in acting like you know everything. You come in as a collaborator. You're the leader, but they are a vital resource. You listen. Jackson: Okay, 'show respect' is great advice, but what does that look like on a Tuesday morning when you have to give negative feedback to someone twice your age? Olivia: That's where the new toolkit comes in. Pollak talks about focusing on solutions, not just problems. And for really tough conversations, she recommends a technique her mom, a business coach, taught her: the "broken record." Jackson: The broken record? Like, just repeating yourself over and over? Olivia: Essentially, yes. You identify your single most important point and you stick to it, calmly and firmly, no matter what counterarguments or emotional tangents come your way. For example, if an employee is consistently late, and they give you a dozen excuses, you don't debate the excuses. You just keep returning to the core message: "I understand, but your punctuality is impacting the team's workflow, and we need to solve that." It avoids getting dragged into drama. Jackson: That's actually brilliant. It's firm without being aggressive. It keeps the focus on the issue, not the person. But you can't lead in a vacuum. You need support. Olivia: Absolutely. This leads to another key idea: building your "Personal Advisory Board." This isn't just one mentor. It's a team of champions. Pollak says you need five types: a Traditional Mentor for wisdom, a Co-Mentor who is a peer you can learn with, a Sponsor who will actively advocate for you, a Peer for unfiltered advice, and even your Mom and/or Dad for unconditional support. Jackson: A whole team. It makes sense. You wouldn't run a company with just one advisor. Why would you run 'You, Inc.' that way? Olivia: And you have to be careful who you choose. There's a story in the book about a woman who asked a mentor for advice on a book deal, and the mentor told her she was too young to ask for that much money. She was being unsupportive, a 'frenemy.' You have to find people who genuinely want you to succeed. Jackson: It seems like the common thread here is that modern leadership is less about command and more about connection and collaboration. Olivia: It is. And that's why insular thinking is so dangerous. Pollak tells the story of a networking expert who pitched a workshop to an executive at Lehman Brothers before their collapse. The executive rejected it, saying, "We don’t need a professional networking workshop. Our employees only need to know each other." Jackson: Oof. That quote did not age well. It’s a perfect cautionary tale. If you only talk to people inside your own bubble, you have no idea when the bubble is about to pop. Olivia: Exactly. The new art of leadership is about building bridges—between generations, between peers, between your team and the outside world. It’s about connection, not just control.

Olivia: When you pull all these threads together—the changing world, the rise of the personal brand, the new art of connection—you see a completely new picture of leadership emerge. Jackson: It feels like the old model was about getting power and holding onto it. This new model is about building influence and sharing it. It's a shift from a fortress to a network. Olivia: That's a perfect way to put it. The old boss was a gatekeeper of information and authority. The new boss is a hub of connection and empowerment. They succeed by making the people around them better, more connected, and more successful. Jackson: And it's not about pretending to be perfect. It's about being authentic, owning your mistakes, and as Pollak says, learning to "fall with style," like Buzz Lightyear. Olivia: (Laughs) Exactly. It's about owning the 'boop' on the nose and moving on. The ultimate goal isn't just to be a good boss, but to create your own unique value. There's this quote Pollak has hanging over her desk that I think sums it all up. Jackson: What is it? Olivia: "You don’t want to be better than the competition. You want to be considered the only one that does what you do." Jackson: Wow. That reframes everything. It’s not about climbing the ladder faster; it’s about building something no one else can. That's a much more inspiring goal. Olivia: It is. And it feels like a much more achievable one for people who are just starting out. Jackson: So for our listeners, what's a good first step? This is a lot to take in. Olivia: Pollak mentions a business owner in the book, Jess Lively, who created an "Only I" list. It's a list of the crucial tasks that only she, as the leader, could do for her business to succeed. Everything else could be delegated. Jackson: I love that. It forces you to define your unique value. So maybe the first step for our listeners is to take 15 minutes and write down their own "Only I" list. What are the three things that only you can bring to your team or your project? Olivia: That's a fantastic, practical takeaway. And we'd love to hear what you come up with. Find us online and share one thing from your "Only I" list with the Aibrary community. It’s a great way to start building that brand. Jackson: This is Aibrary, signing off.