
The Art of Leading Up
12 minGolden Hook & Introduction
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Olivia: Most leadership books are written for CEOs. They're filled with advice on corporate vision and shareholder meetings. They're basically useless for the 99% of us who aren't in charge. Jackson: Right. And the advice we usually get is some version of "Just do your job, keep your head down, and wait your turn." It’s the career equivalent of being told to sit in the corner and be quiet. Olivia: Today, we're exploring a book that argues that is the absolute worst advice you could ever take. The core premise of How to Lead When You're Not in Charge by Clay Scroggins is that waiting for a title is the fastest way to kill your leadership potential. Jackson: And Scroggins is such an interesting person to write this. He has this really unusual background—he got a degree in Industrial Engineering from Georgia Tech, a field all about optimizing systems, but then he spent his entire career in ministry, eventually becoming a lead pastor at a massive church. Olivia: Exactly. He brings an engineer's mind for systems and a pastor's deep understanding of people. He argues that the waiting room of leadership isn't a place to sit passively; it's the training ground. It's where the real work begins. And that work doesn't start with managing a team or a budget. It starts with a question most of us never think to ask. Jackson: Which is? Olivia: If a title doesn't make you a leader, what does? Scroggins argues the answer is your identity. And for most of us, that’s where the problem begins.
The Identity Crisis: Leadership Begins with 'Who,' Not 'What'
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Jackson: Okay, I have to be honest, when I hear the phrase "identity crisis," I picture a college student with a philosophy textbook or a movie character staring into a mirror. It sounds a bit... abstract for a Tuesday morning meeting. How does this actually show up at work? Olivia: That's the perfect question, because it shows up in ways we don't even recognize. Scroggins uses this great analogy of a fake ID. You know, you're trying to get into a club you're not supposed to be in, so you present this false version of yourself. You're nervous, you're looking over your shoulder, you can't relax. He says many of us lead with a "fake ID." We're performing a role we think we're supposed to play, instead of leading from who we actually are. Jackson: Huh. So you’re not talking about literally lying on your resume. You’re talking about a psychological fake ID. Olivia: Precisely. The book points to these common identity traps that feel almost cinematic. One is what he calls "choosing from multiple passports," which is straight out of The Bourne Identity. Jason Bourne has a safe deposit box with a gun, cash, and six passports with his face but different names. He can be anyone the situation requires. A lot of us do this at work—we have a "passport" for when we're with our boss, another for our team, another for clients. We shift our identity to fit the room. Jackson: And that’s exhausting. You can never just be yourself. What's another trap? Olivia: The other big one is chasing an identity to please someone else, which is the story of Frank Abagnale Jr. in Catch Me If You Can. He becomes a pilot, a doctor, a lawyer—all in a desperate attempt to win back his father's approval and put his broken family back together. His entire identity is built on external validation. Jackson: Wow, that hits close to home. Maybe not the forging checks part, but the feeling that your entire sense of self-worth for the day can be made or broken by a single email from your boss. One critical comment, and you feel like a total failure. One line of praise, and you're on top of the world. Olivia: That's it exactly! That's the identity crisis in action. Your sense of "who you are" is completely tied to "what you do" and how people react to it. Scroggins argues that true leadership, the kind that has influence even without a title, has to be grounded in something more stable. It's about knowing your own value, your purpose, and your principles, independent of your job performance or your boss's mood. Jackson: So it's about building an identity that's weatherproof. It doesn't get washed away by the first storm of criticism. Olivia: Exactly. Because if your identity is fragile, you'll either be too scared to take any risks, or your ambition will become this needy, selfish thing. You're not trying to make things better; you're just trying to prove you're good enough. Jackson: That makes so much sense. If your identity is fragile, your ambition becomes distorted. Which I think is the next huge idea in the book, this battle between two very similar-sounding words.
Reclaiming Ambition: The Battle Between 'Kabash' and 'Kibosh'
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Olivia: It is. And this is where Scroggins' theological background really shines in a fascinating way. He argues that ambition itself isn't the problem. The problem is that we've forgotten its original purpose. He goes all the way back to the book of Genesis, to the Hebrew word 'kabash'. Jackson: Kabash. Okay, what does that mean? Olivia: In Genesis, humanity is given the mandate to 'kabash' the earth. It's often translated as 'subdue,' which sounds aggressive. But Scroggins reframes it. Think of a gardener. A gardener 'subdues' the weeds, the soil, the water—not to destroy them, but to organize them, to cultivate them, to bring all the elements together so that something new and fruitful can grow. 'Kabash' is the ambition to create order and flourishing. Jackson: I like that. It’s ambition as cultivation, not conquest. It's about making the garden better. Olivia: Exactly. Now, contrast that with another word: 'kibosh'. Jackson: Ah, the kibosh! I know the kibosh. That's what my landlord puts on my dreams of getting a dog. Olivia: (laughing) Precisely! And Scroggins brings up the perfect pop culture reference: the sitcom Seinfeld. There's an episode where the character "Crazy" Joe Davola thinks Jerry bad-mouthed him to TV executives, and he leaves this menacing message on Jerry's answering machine, saying, "I'm gonna put the kibosh on you. You know I've kiboshed before, and I will kibosh again." Jackson: That's hilarious. So a 'kibosh' leader is basically "Crazy" Joe Davola in a business suit. They're the person in the meeting whose only contribution is to shoot down every new idea. The professional dream-killer. Olivia: You've nailed it. The 'kibosh' leader, whether they're in charge or not, is the one who says, "No, we can't do that. We tried that five years ago. That's not how we do things here." Their ambition is twisted into negativity and control. A 'kabash' leader, on the other hand, is the one who hears a problem and, even if they have no authority, says, "That's a tough challenge. What if we tried this? How could we make that work?" Jackson: So this reframes ambition entirely. It's not about climbing the corporate ladder for your own sake. It's about a fundamental drive to make your little corner of the world—your team, your project, your process—more fruitful. To be a gardener. Olivia: Yes. And that drive to improve things, to 'kabash' your environment, is what gives you influence. It's not about asking for power; it's about demonstrating value. But that drive inevitably leads you to the most dangerous territory for someone who's not in charge. Jackson: Let me guess. Your boss's office. Olivia: Exactly. It leads to the art of challenging up.
Challenging Up: The Art of Influencing Your Boss
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Jackson: This is the part that makes everyone nervous. Because in most companies, "challenging up" is a politically correct term for "getting yourself fired." How do you actually do this without committing career suicide? Olivia: Scroggins provides one of the best case studies I've ever read on this, and it involves a product we all know: the Chick-fil-A milkshake. Jackson: The milkshake? I'm listening. Olivia: In the mid-2000s, Chick-fil-A was exploding, but customers kept asking for one thing they didn't have: hand-spun milkshakes. The problem was, corporate headquarters had put the 'kibosh' on the idea. Their entire brand was built on speed of service, and they believed making milkshakes would grind their drive-thrus to a halt. Jackson: A classic 'kibosh' moment. The system is designed to resist change. Olivia: Exactly. But a franchise owner in Georgia named Shane Todd was a 'kabash' leader. He saw the potential. So, he started a covert operation. He bought a blender, developed a recipe, and began secretly selling milkshakes in his store. And they were a massive hit. Jackson: He went rogue! I love this. But how did he not get shut down immediately? Olivia: Oh, he almost did. The regional vice president, a man named Woody Faulk, heard about this rogue milkshake operation and came to investigate. But Shane had built a strong relationship with him. He didn't just complain about the corporate policy; he invited Woody in. He showed him the sales numbers. He showed him the happy customers. He was presenting a solution, not a problem. Jackson: He had data. He wasn't just saying "I want to sell milkshakes." He was saying "My customers want to buy milkshakes, and here's the proof." Olivia: And here’s the brilliant part. The Senior VP of Operations, Tim Tassopoulos, eventually came to the store, still convinced it was too slow. He was ready to shut it down. Shane knew Tim's core value was speed. So he didn't argue. He proposed a challenge. He said, "Tim, you stand at the counter and make two Diet Cokes. I'll make a milkshake. Let's see who's faster." Jackson: No way. What happened? Olivia: Shane won. He had perfected his process. He proved that he could deliver a high-quality product without sacrificing the company's core value. He didn't challenge Tim's authority; he honored Tim's priority—speed—and showed him a better way. The milkshake was rolled out nationwide and became one of their most successful products ever. Jackson: That is an incredible story. So the secret to challenging up isn't about having a big confrontation. It's about doing your homework. It's about understanding what your boss actually cares about—the 'why' behind their 'no'—and then building a bridge from your idea to their priority. Olivia: That's the whole playbook. Build the relationship first. Don't make it personal. Frame your challenge as a way to help them win. And be prepared to show, not just tell. Shane Todd didn't write a memo; he built a working model and proved its success. He led without being in charge, and in doing so, he changed the entire company.
Synthesis & Takeaways
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Jackson: It really feels like a three-step process then, when you lay it all out. First, you have to do the internal work. You have to fix your own identity so you're not leading from a place of fear or neediness. Your leadership has to be grounded in who you are, not the title you have. Olivia: Right. The 'who' before the 'what'. Jackson: Second, you channel your natural ambition away from selfish 'kibosh' energy and toward productive 'kabash' energy. You become a gardener, focused on cultivating and improving whatever is in front of you, making things better for everyone. Olivia: And that's what earns you the influence. Jackson: And only then, once you've done that work, have you earned the right and, more importantly, the wisdom to 'challenge up' effectively. You're not just a complainer anymore; you're a trusted problem-solver, like Shane Todd with his milkshake. Olivia: Exactly. And the book's final, powerful message is summed up in a simple phrase Scroggins repeats: "As now, so then." The way you handle your responsibilities now, the way you treat your colleagues now, the way you lead from the middle of the pack now—that is the best predictor of the leader you will be when you are in charge. Jackson: There's no magic switch that flips when you get a promotion. You take your current self into that new role. Olivia: You do. Leadership isn't a future event; it's a present practice. So the question for everyone listening is: what's one small thing you've been passively accepting at work or in your life—a broken process, a recurring frustration—that you could start actively trying to improve this week? Not by demanding change, but by starting to cultivate a solution. Jackson: A fantastic question to end on. It’s about starting your next chapter today, not waiting for someone else to write it for you. Olivia: This is Aibrary, signing off.