Olivia: Most leadership books sell you a fantasy: that with the right formula, you can control the future. This book argues the exact opposite. Jackson: Oh, I like where this is going. Olivia: The best leaders aren't masters of control; they're masters of admitting they have no control. And that's their superpower. Jackson: That feels both terrifying and incredibly liberating. It’s like you’re telling me the secret to flying is to stop flapping my arms so hard and just… notice the wind. Olivia: That’s the radical idea at the heart of Simple Habits for Complex Times by Jennifer Garvey Berger and Keith Johnston. It’s a guide for leading when the map is useless and the territory is changing under your feet every single day. Jackson: And these authors aren't just theorists throwing ideas from an ivory tower. Garvey Berger has a doctorate from Harvard in adult development, and they both coach top-level executives at places like Google and Microsoft. They're in the trenches of complexity. Olivia: Exactly. They saw that the old leadership playbook—the one based on predicting, planning, and controlling—was failing spectacularly in the modern world. So they created a new one, based on simple, powerful mental habits. To see why this is so necessary, let's start with a leader whose world is completely falling apart.

Olivia: Meet Yolanda Murphy. She’s the director of a statewide Family and Children’s Services division, or FACS. And her division is in a full-blown, five-alarm crisis. Jackson: I’m already stressed just hearing her job title. That sounds like one of the hardest jobs in the world. Olivia: It is. And in the last 18 months under her leadership, six children in their care have died, and four more have been hospitalized. The press is calling it a systemic failure. The public is demanding her resignation. And as the book opens, her assistant rushes in with news of another case: a ten-year-old boy, abused in a foster home. Jackson: Oh, man. That’s just brutal. What can you even do in a situation like that? The pressure must be immense. Olivia: It’s overwhelming. The book describes her sitting at her desk, so frustrated she slams her fist on the keyboard. Her second-in-command, Doug, is trying to pull data, trying to find a root cause, but it’s a mess. The boy who was just abused had a history of starting fires. The foster family he was placed with was on probation for previous abuse allegations. The system is a web of interconnected failures. Jackson: It sounds like a classic VUCA situation—Volatile, Uncertain, Complex, and Ambiguous. Every string you pull is tangled with ten others. There’s no simple "who's to blame?" answer. Olivia: Precisely. And that’s where the book introduces its first, most fundamental habit for complex times: Asking Different Questions. Yolanda’s instinct, and the public’s demand, is to ask, "Whose fault is this? Who do I fire?" But that’s a question for a simple, predictable world. In a complex world, that question just leads you down a rabbit hole of blame and doesn't solve anything. Jackson: Okay, but 'asking different questions' can sound a bit… soft, when children are in danger. How does that actually help? What other question is there to ask? Olivia: It’s not about being soft; it’s about being a better diagnostician. Instead of "Who's to blame?", a more powerful question is, "What is this system designed to produce?" Or, "What conditions are we creating that allow for these tragedies to happen?" It shifts the focus from finding a scapegoat to understanding the environment. This is where the second habit comes in: Taking Multiple Perspectives. Jackson: You mean, trying to see the situation from the viewpoint of the overworked caseworker, the scared child, the angry journalist, the under-resourced foster family? Olivia: Exactly. Right now, Yolanda is just seeing enemies and problems. But each of those perspectives holds a piece of the truth about why the system is failing. The book argues that leaders in complexity have to stop seeing people as problems to be solved and start seeing them as sensemakers who can help you understand the whole picture. Jackson: That’s a huge mental shift. It’s moving from being a general in a war room to being a detective at a crime scene, trying to piece together clues from every witness, even the ones you don’t like. Olivia: A perfect analogy. Because you can't fix a system you don't understand. And you can't understand it from a single vantage point. This leads directly to the third, and perhaps most powerful, habit.

Olivia: Yolanda's problem, and your question about finding real leverage points, brings us to the third habit: Seeing the System. And the best story to illustrate this doesn't come from a corporate boardroom, but from a warzone. Jackson: I’m intrigued. This is a big leap from a government office. Olivia: The book tells the story of a US Army Major stationed in Kufa, Iraq, in 2003. His problem was that violent gatherings and riots were escalating. The standard military playbook would be to increase patrols, show more force, and impose curfews—to try and control the population. Jackson: Right, the command-and-control approach. Clamp down on the problem. Olivia: But the Major decided to try something different. He just watched. He studied videotapes of the riots and looked for patterns. He saw that a crowd would gather in a plaza. Then, food vendors would show up, selling snacks and drinks. The crowd would linger, grow larger, and then someone would throw a rock or a bottle, and everything would explode into violence. Jackson: Huh. The food vendors. That’s a detail most people would completely ignore. Olivia: He saw it as part of the system. So, he didn't call for more troops. He went to the mayor of Kufa and asked for a simple ordinance: no food vendors allowed in the plazas. Jackson: Wait, that’s it? The solution to riots was… no more food trucks? That sounds way too simple. How could that possibly work? Olivia: Because it disrupted the system at a key leverage point. The next time a crowd gathered, they got restless. Then they got hungry. And with no food available, they just… went home for dinner. The riots stopped. He didn't have to fire a single shot. Jackson: That is brilliant. Absolutely brilliant. He didn't fight the system; he just tweaked one small, seemingly insignificant part of it. It’s like instead of trying to build a massive dam to stop a river, he just diverted a tiny stream that was feeding into it. Olivia: That’s the essence of leading in complexity. You stop looking for complicated, grand solutions and start searching for simple rules or "safe-to-fail experiments" that can nudge the system in a new direction. The book calls this shifting your focus from the probable to the possible. Jackson: What do you mean by that? Olivia: The probable is what you predict based on the past. "If we do X, Y will probably happen." That works for simple problems. But in complex systems, the past is a terrible predictor of the future. The Major couldn't predict that removing food vendors would work. But he saw it as a possibility worth trying—a small experiment where the cost of failure was low. Jackson: So this connects back to Yolanda. Her goal shouldn't be to write a 500-page report to "fix" the entire child welfare system at once. It's about finding those small, safe-to-fail experiments. Maybe it's changing one reporting metric, or trying a new community outreach program in one city. Olivia: Precisely. See the system, find a small thing to nudge, and see what happens. But of course, as you said earlier, systems are made of people. And people are wonderfully, maddeningly, complex themselves.

Jackson: So we have these three habits: new questions, multiple perspectives, and seeing systems. But systems are made of people. And people are… messy. How do you handle the human side of this? The part where you actually have to talk to them? Olivia: I’m so glad you asked, because the book dives into this with another painfully relatable story. Meet Jarred. He’s a newly promoted manager at a software company. He’s smart, he’s a good engineer, but he’s new to leading people. Jackson: I feel for Jarred already. Olivia: His story starts with him getting a brutal performance review from his own boss, Murray, who basically tells him he's failing as a leader. Jarred leaves the meeting feeling demoralized and attacked. Then, he has to turn around and give a performance review to his most difficult team member, a remote employee named Michelle who is brilliant but argumentative. Jackson: Oh, this is a recipe for disaster. He’s going into that conversation wounded and defensive. Olivia: Completely. He walks into the conference room with a list of all the things Michelle does wrong. He tries the classic "feedback sandwich"—a little praise, then the criticism, then more praise. It fails spectacularly. Michelle immediately turns the tables and starts critiquing his leadership and the company's strategy. Jackson: Oh, I've been in that meeting. We all have. It's so cringeworthy and painful. You can feel the defensiveness radiating from both sides. Olivia: It’s a total communication breakdown. Jarred is trying to "fix" Michelle, to prove he's right and she's wrong. And Michelle is doing the exact same thing back to him. The conversation goes nowhere. This is where the book introduces another crucial mindset shift for leaders: see your people as sensemakers, not as problems to be solved. Jackson: What does that mean, a 'sensemaker'? Olivia: It means that Michelle isn't just being difficult for the sake of it. Her arguments, her criticisms—they are data. She holds a piece of the puzzle. She sees the system from a perspective that Jarred, as her manager, cannot. The purpose of a feedback conversation in a complex world isn't for the supervisor with "super-vision" to correct the employee. It's a dialogue to merge two different views of reality. The goal isn't to win the argument; it's to learn what the other person sees. Jackson: That changes everything. The goal is learning, not correcting. So Jarred’s job wasn't to tell Michelle she was wrong, but to ask questions to understand why she felt the way she did. Questions like, "Help me understand what you're seeing about our company strategy that I'm missing." Olivia: Exactly! And this is where that narrative style some readers find a bit tricky really pays off for me. You feel Jarred's failure, and it makes the lesson about feedback so much more powerful than a dry bullet-point list. You understand on a gut level why the traditional approach fails. The book's point is that you have to grow your people to be bigger than your problems. You don't do that by telling them they're wrong; you do it by creating a feedback-rich environment where it's safe to learn and share perspectives. Jackson: It’s about cultivating a growth mindset, not just in individuals, but in the entire organization. And that starts with the leader being humble enough to admit they don't have all the answers and being curious enough to find them in their own people. Olivia: That’s the heart of it. You can't navigate complexity alone.

Olivia: So, all these stories—Yolanda's overwhelming crisis, the Army Major's clever solution to riots, Jarred's awkward feedback meeting—they all point to the same profound truth. Leadership in complex times isn't about having a perfect map. It's about developing the senses of a skilled explorer. Jackson: Right. You can't predict the terrain, so you have to get better at reading it in real-time. The book's title is perfect. They are simple habits—ask a different question, look from another angle, notice a pattern. But they are for complex times. It’s about being certain of your uncertainty and using that as a strength. Olivia: And the power of the book is that it doesn't just give you theory. It gives you practices. So the call to action is simple, too. This week, in one difficult conversation or one complex problem you're facing, just try one of the habits. Jackson: Don't try to solve the whole thing. Just ask one different question than you normally would. Or, before you respond, genuinely pause and try to articulate the situation from the other person's perspective, even if you disagree with it. Olivia: It's a small experiment. Safe to fail. But it might just change the entire dynamic. It might reveal a new possibility you never would have seen otherwise. Jackson: And we'd love to hear how it goes. What's the one 'different question' you asked? Or what new perspective did you uncover? Find us on our socials and share your story. We're all learning to navigate this complexity together. Olivia: This is Aibrary, signing off.