Olivia: Alright Jackson, I have a question for you. What is the single dumbest, most pointless rule you've ever had to follow at a job? Jackson: Oh, I've got one. I worked at a place where you had to fill out a three-part carbon copy form to get a new pack of pens from the supply closet. You needed a manager's signature. For pens. Olivia: For pens! That is beautifully absurd. It’s the perfect entry point for the book we’re talking about today, because it argues that rules like that aren't just annoying—they're a sign of broken leadership. Jackson: I felt that in my soul. What’s the book? Olivia: It’s Great Leaders Have No Rules by Kevin Kruse. And what’s interesting is that Kruse isn't an academic theorist; he's a serial entrepreneur who built and sold multiple multimillion-dollar companies. So these ideas were forged in the fires of real-world business, which is why the book has this reputation for being so provocative and contrarian. Jackson: An author who has actually done the thing he’s writing about. A rare species. So he’s against rules for pens, I take it? Olivia: He’s against almost all of them. He believes the entire corporate rulebook is often a substitute for actual leadership.

Jackson: Okay, but hold on. A company with no rules? That sounds like pure chaos. How do you control costs? How do you make sure people do their jobs? Isn't that the whole point of management? Olivia: That’s the exact assumption Kruse wants to dismantle. He argues that most rules aren't about creating order; they're about avoiding the hard work of trusting people. And they often lead to dumber, more expensive outcomes. He tells this fantastic story from early in his career. Jackson: I’m ready. Hit me with it. Olivia: He had just sold his company and was now a VP at the acquiring firm. He submits his first expense report, and the check comes back short by four dollars and thirty-four cents. He emails the CFO, a very by-the-book guy, asking what happened. Jackson: I’m already annoyed on his behalf. What did the CFO say? Olivia: The CFO replies, and this is a direct quote, "I deducted $4.34 because we don’t allow employees to buy Post-it notes." Jackson: You have got to be kidding me. Post-it notes? What was the rationale? Olivia: The CFO called them a "wasteful expense" and said it was "cheaper to tear regular paper into little squares." Jackson: Wow. That is a level of micromanagement I can barely comprehend. It’s so focused on the four dollars that it completely ignores the cost of the VP’s time, the CFO’s time, and the sheer drop in morale from being treated like a child. Olivia: Exactly! Kruse says this tiny incident sparked a company-wide "Post-it note debate." It’s the perfect example of his point: rules are often applied to activities—like buying Post-its—when what really matters is the outcome. The rule doesn't make the company more profitable; it just makes smart people feel untrusted and stupid. Jackson: That makes so much sense. But that’s a small-stakes example. What about bigger rules, like travel policies? You can’t just let people spend whatever they want. Olivia: Ah, but that’s where it gets even more interesting. Kruse shares another story about a company that implemented a very strict travel rule to save money. The rule was: all employees on business travel must stay at a Motel 6 or a cheaper equivalent. No exceptions. Jackson: Okay, I can see the logic. They’re trying to standardize and prevent people from booking suites at the Four Seasons on the company dime. Olivia: A reasonable goal. But then an employee is on a trip in Duluth. He gets to the local Motel 6, and it’s completely full. Right next door is a Super 8 motel, which would cost an extra ten dollars for the night. Jackson: So he stays at the Super 8, right? It’s the only logical thing to do. Olivia: Nope. The rule is the rule. The employee, wanting to be a good soldier and follow the policy, gets back in his car. He spends $250 on a rental car to drive four hours to the next town that has a Motel 6 with a vacancy. Jackson: Oh, come on. That’s insane! The company lost hundreds of dollars and half a day of his work time to save ten bucks. Olivia: And that is the core of the "No Rules" philosophy. The rule prevented the employee from using his own brain. It optimized for compliance, not for the best outcome. Kruse points to companies like Netflix, whose famous expense policy is just five words: "Act in Netflix's best interests." Jackson: That’s a guideline, not a rule. It trusts the employee to think like an owner. So the alternative to a thousand nitpicky rules is to hire responsible adults, give them a clear standard to aim for, and then hold them accountable for the results. Olivia: Precisely. You don't need a rule about Post-it notes if you trust your team to manage a budget. You don't need a Motel 6 rule if you trust them to be frugal. It’s about replacing control with accountability.

Jackson: Okay, so breaking the company rulebook makes sense when you put it like that. But the book's contrarian streak doesn't stop there. Kruse also talks about breaking the unwritten rules of being a leader—like the idea that you always have to be strong, perfect, and stoic. That feels even riskier. Olivia: It does, because it cuts to the core of our image of a leader. We think of leaders as unflappable, almost superhuman. But Kruse argues that true strength lies in showing weakness. He points to a psychological phenomenon called the "pratfall effect." Jackson: The pratfall effect? What’s that? Olivia: It was first studied in the 60s. Researchers had students listen to a recording of someone trying out for a quiz show. The contestant is brilliant, answering almost every question correctly. In one version of the recording, that’s all that happens. In the second version, after acing the quiz, the contestant clumsily spills a cup of coffee all over themselves. Jackson: And I’m guessing the clumsy one was less popular? Olivia: The opposite. The students found the brilliant person who committed the "pratfall" significantly more likable. The mistake didn't make him seem less competent; it made him seem more human, more relatable. Spilling the coffee bridged the gap. Jackson: Huh. So making a mistake can actually be a superpower. It makes people connect with you. It’s not about being perfect; it’s about being perfectly human. Olivia: Exactly. And Kruse argues this is essential for modern leaders. In a world that demands trust and collaboration, a leader who pretends to be a flawless robot can’t build real connections. He shares this incredibly powerful story about Brandon Brooks, an offensive lineman for the Philadelphia Eagles. Jackson: A giant of a man. We're talking six-foot-five, 340 pounds. The epitome of physical strength. Olivia: The epitome. In 2016, he signed a massive $40 million contract. He should have been on top of the world. But on game days, he would wake up with crippling stomach pain and uncontrollable vomiting. It was so bad he had to miss several crucial games. The media called it a "mysterious illness." Jackson: That sounds terrifying. What was going on? Olivia: For weeks, no one knew. Then, Brooks did something almost unheard of in the hyper-masculine world of the NFL. He held a press conference and told the world the truth: he had a severe anxiety condition. He explained that his obsession with being perfect, with never making a single mistake on the field, was literally making him sick. Jackson: Wow. To admit that, in that environment, takes a different kind of strength. What happened after he showed that vulnerability? Olivia: Everything changed. His coaches and teammates rallied around him. He started seeing a psychologist. He learned to let go of the need for perfection and to accept that mistakes happen. The very next season, after embracing his "weakness," he didn't miss a single game, was nominated to the Pro Bowl, and his team, the Eagles, won the Super Bowl. Jackson: That’s an amazing story. His vulnerability didn't make him weaker; it unlocked his true potential. It allowed him to get the help he needed to become even better. Olivia: And that's the lesson for leaders. Sharing your struggles, admitting when you're wrong, or saying "I don't know" isn't a failure of leadership. It's an act of trust-building. It gives your team permission to be human, too. It creates psychological safety, which is the bedrock of innovation and engagement. Jackson: I can see that. But I have to ask the question I’m sure many listeners are thinking: is there a line? Can a leader be too vulnerable? If my boss comes in every day talking about their anxieties, at some point, I might lose confidence in their ability to lead the ship. Olivia: That’s a fantastic and crucial question. And Kruse is clear on this. It’s not about oversharing or emotional dumping. The goal of vulnerability in leadership isn't to get sympathy; it's to build trust and model authenticity. It's the difference between saying, "I'm really struggling with this strategic problem, and I'd love to get your thoughts," versus, "I'm so overwhelmed, I don't think we're going to make it." Jackson: Ah, one is an invitation to collaborate, the other is an invitation to panic. Olivia: Exactly. One shows humility and respect for your team. The other undermines confidence. It’s about being authentic, not about abdicating your role as a confident leader.

Jackson: So when you put it all together, it seems like the book is really about tearing down two different kinds of walls. Olivia: That’s a great way to put it. What do you mean? Jackson: Well, the "No Rules" idea is about tearing down the external walls—the policies, the handbooks, the bureaucratic nonsense that prevents people from using their judgment. It’s a shield the organization uses to avoid trusting its people. Olivia: I like that. And the second wall? Jackson: The second wall is internal. The "Show Weakness" idea is about tearing down the leader’s personal shield of perfection. The need to be seen as flawless, all-knowing, and invulnerable. Kruse is essentially saying that great leaders have the courage to drop both shields. Olivia: And in doing so, they create a space for trust, accountability, and genuine human connection to thrive. He argues that in the end, leadership isn't a choice. We are all influencing the people around us, all the time, for better or for worse. The only choice we have is whether we do it with intention. Jackson: It’s a powerful shift in perspective. It’s not about mastering a set of rules, but about cultivating a certain way of being. It’s about being a leader people want to follow, not one they have to obey. Olivia: And that really comes down to one thing he repeats throughout the book: great leaders care. They care enough to trust their people, and they care enough to be real with them. So, for everyone listening, here’s a reflective question to take with you. Jackson: Let's hear it. Olivia: What's one rule—either a formal one in your company's handbook, or an unwritten one in your own head about how you're 'supposed' to act—that you could challenge this week? Jackson: A great question to ponder. Olivia: This is Aibrary, signing off.