Olivia: Most people think their résumé should be a highlight reel of pure success. But what if the most important line on it is actually your biggest failure? And what if the world's top CEOs agree? Jackson: That is the opposite of everything I have ever been told about job hunting. My entire life has been about hiding the failures and polishing the wins. You’re telling me I’ve been doing it wrong? Olivia: You and everyone else. And it's one of the core, unexpected lessons from Adam Bryant's fantastic book, The Corner Office: How Top CEOs Made It and How You Can Too. Bryant isn't just some theorist; he ran the famous column of the same name for The New York Times. Jackson: Oh, I remember that column. It was always so insightful. Olivia: It was. And for the book, he distilled the wisdom from over a decade of interviews with more than 500 CEOs and top executives. He was looking for the patterns that defy conventional wisdom. Jackson: Five hundred CEOs. That’s not a focus group; that's a massive dataset on what it actually takes to lead. Okay, let's start with that failure idea from the top. Are you seriously saying a CEO would rather hire someone who has failed spectacularly than someone with a perfect, clean record?

Olivia: In many cases, yes. But it's not about the failure itself. It's about what it produces. Bryant gives this quality a name: "battle-hardened confidence." This isn't the slick, easy confidence of someone who has never been challenged. This is a quiet, deep resilience that's been forged in the fire of adversity. CEOs say it's the single most valuable trait, and also the hardest to screen for. Jackson: Okay, but how can you even tell if someone has that? It's not like you can put 'survived a disastrous project launch' on your LinkedIn profile and expect a call back. How do you prove you have this grit? Olivia: That’s the secret. They don't look for the failure on the résumé; they listen for it in the story. They want to know how you talk about it. Bryant shares this incredible, almost folkloric story from Carol Bartz, the former CEO of Yahoo. She grew up quite poor on a farm in Wisconsin, raised by her grandmother. Jackson: I'm listening. Olivia: One day, when she was about thirteen, she and her brother found a snake in the rafters of a shed. They did what most kids would do—they ran screaming to their grandmother. Her grandma, without missing a beat, came out with a shovel, knocked the snake down, chopped its head off, and then turned to them and said, "You could have done that." Jackson: Whoa. That is a line that sticks with you. "You could have done that." It’s so simple but so powerful. It’s not about the snake at all, is it? It’s about instilling this sense of self-reliance. Olivia: Exactly. It’s about building what psychologists call an "internal locus of control"—the belief that you shape your circumstances, not the other way around. And that's what CEOs are digging for. It’s why a company like Accenture, which gets two million résumés a year, developed a system called 'critical behavior interviewing.' Their entire process is built on one premise. Jackson: Let me guess: tell us about a time you failed? Olivia: Pretty much. William Green, Accenture's CEO, says their core question is, "Have you faced any adversity, and what did you do about it?" They're not listening for excuses or blame. They're listening for ownership. They're listening for the person who says, "Here's what went wrong, here's what I learned, and here's how I fixed it." Jackson: This also helps explain something I've heard about the book. Some readers find the advice a bit conventional—I mean, "learn from your failures" isn't exactly a groundbreaking idea. But it sounds like Bryant's real contribution isn't the what, but the how. He's showing how leaders actually test for this in the real world. Olivia: That's the perfect way to put it. The book is full of these practical applications. John Donahoe, the CEO of eBay, tells a story about how he used to be terrified of failure. A mentor finally told him, "You're trying to bat .900." He pointed out that the best hitters in Major League Baseball are considered legends if they bat .300. They fail seven out of ten times. That analogy completely reframed failure for him—it became a statistical necessity for taking big swings. Jackson: I love that. It makes failure feel less like a personal flaw and more like a part of the process. You have to take the at-bats to get the hits.

Jackson: That baseball analogy is a perfect pivot, actually. It feels like it connects to another huge idea in the book that I found totally fascinating—this concept that we're thinking about our entire career paths all wrong. Olivia: You're talking about the death of the career ladder. This was one of my favorite parts of the book. Bryant highlights the thinking of Barbara Krumsiek, a CEO who argues that the 'career ladder' is a deeply flawed, even toxic, metaphor. It suggests a linear, one-person-at-a-time climb. Jackson: And it implies that to move up, you have to wait for the person above you to move on, or worse, you have to push them off. It's inherently competitive and zero-sum. So what's the alternative? A career escalator? Olivia: (laughing) Even better: a career "obstacle course." Krumsiek's point is that on an obstacle course, there are many people on the course at once, all running their own race. And here's the beautiful part: you can stop and help someone else get over a high wall, and it doesn't prevent you from finishing your own course. It's collaborative, not cutthroat. Jackson: That is such a brilliant reframe. It also just feels more… true. My career has definitely felt more like a muddy, unpredictable obstacle course than a neat, orderly ladder. So if it's an obstacle course, how do you train for it? Olivia: This is where another great visual from the book comes in, this time from Carol Bartz again. She says you should build your career not as a ladder, but as a pyramid. A ladder is inherently unstable—one narrow path up. A pyramid, on the other hand, has a wide, solid base of experience. Jackson: And how do you build that base? Olivia: By doing things that don't look like 'climbing.' You take lateral moves. You work in a different department. You take a job that seems like a step sideways because it teaches you a new skill. You're building a broad foundation so that when opportunities arise, you're stable and ready for them from any direction. Jackson: So the goal isn't just 'up,' it's 'broader.' That feels so much less stressful. It means that weird job you took in your twenties wasn't a waste of time. Bryant mentions Guy Kawasaki, the tech evangelist, who started out schlepping diamonds in the jewelry business. On a ladder, that's a totally different career. On a pyramid, he was learning sales and persuasion—building the base. Olivia: Precisely. It’s about preparation, not a rigid plan. As Clarence Otis Jr., the CEO of Darden Restaurants, says in the book, "It’s not about career planning; it’s about preparation and building skills." The obstacle course is unpredictable. You can't plan the route, but you can be prepared with a wide range of skills to handle whatever comes next.

Jackson: So when you put these two big ideas together—this battle-hardened confidence born from failure, and this career-as-an-obstacle-course model—a really clear picture starts to emerge. It seems the path to the corner office isn't a straight, polished, perfect line. It's a messy, resilient, and highly adaptive journey. Olivia: That's the deep insight that runs through the whole book. Adam Bryant reveals that leadership isn't about having a perfect track record. It's about having an interesting one. It's about collecting scars and stories that prove you've been tested. The hundreds of CEOs he interviewed aren't looking for flawless, cookie-cutter employees; they're looking for resourceful, creative problem-solvers. Jackson: And that is an incredibly empowering thought for our listeners. It means that setback you had last year, or that sideways career move that felt like a mistake at the time, might actually be your biggest asset. It’s part of your story. It's a piece of your pyramid. Olivia: It completely reframes our relationship with our own professional lives. The stumbles are as important as the sprints. So, we want to leave our listeners with a question to reflect on: What's a 'failure' or a 'detour' in your past that, looking back now, actually built a key part of your 'pyramid'? Jackson: We'd genuinely love to hear your stories. Find us on social media and share how you've navigated your own obstacle course. It’s a conversation worth having. Olivia: This is Aibrary, signing off.