Olivia: Alright Jackson, what's the first rule of a successful team project? Jackson: Easy. Get everyone on the same page, right? Harmony, a clear plan, zero drama. Olivia: That's what we all think. But what if that very instinct—the drive for harmony—is exactly why most important collaborations fail? Jackson: Hold on, you’re saying getting along is… bad? That feels like saying the secret to a good cake is leaving out the sugar. It just doesn't compute. Olivia: It’s a wild thought, but it’s the central premise of the book we’re diving into today: Collaborating with the Enemy: How to Work with People You Don’t Agree with or Like or Trust by Adam Kahane. And Kahane isn't some armchair theorist. This is a guy who has spent decades as a professional facilitator in over fifty countries. Jackson: Wow, okay. So he’s not just talking about office politics. Olivia: Not at all. He’s worked with everyone from corporate executives and government ministers to actual guerrillas and army generals in post-conflict zones. He’s seen collaboration at its most extreme, and his conclusion is that our conventional playbook is fundamentally broken, especially when the stakes are high. Jackson: So he’s basically a collaboration Navy SEAL. That definitely changes things. If he’s saying harmony is the problem, I’m suddenly very interested in what the solution is.

Olivia: Well, the solution starts by diagnosing the problem correctly. Kahane calls our usual approach "conventional" or "constricted" collaboration. It’s built on a few core assumptions: that we can get everyone to agree on a goal, create a clear plan, and then control the execution. It looks like a perfect, orderly planning meeting. Jackson: Right, which sounds like every corporate off-site I've ever been to. A facilitator comes in, we do trust falls, we make a five-year plan, and everyone nods. What’s so wrong with that? Olivia: Because in any truly complex situation, that harmony is an illusion. Kahane tells this fantastic, and slightly painful, story about a hospital CEO named Susan Jones. Her hospital was struggling—financially, clinically, everything. So she did exactly what you’d expect. Jackson: Let me guess: she hired expensive consultants. Olivia: You got it. She brought in the top 25 managers for a big off-site workshop. The consultants presented their diagnosis and a brilliant, comprehensive transformation plan. Everyone debated, they reached a consensus, they assigned tasks, and they all left feeling aligned and energized. Jackson: Sounds like a success story so far. Where does it go wrong? Olivia: The moment she announced the plan to the rest of the hospital staff—the doctors, nurses, technicians. They met it with total cynicism and resistance. They saw it as just another top-down mandate from managers who didn't understand their reality. Implementation got bogged down, costs skyrocketed, and here’s the kicker: the hospital's clinical and financial results actually got worse. Jackson: Oof. That is painfully familiar. It’s like every grand corporate initiative that everyone secretly makes fun of by the water cooler. So the mistake wasn't the plan itself? Olivia: Exactly. The mistake was the belief that one perfect plan, created by a small group in a controlled environment, could be imposed on a complex, messy system with thousands of people who all have different needs, interests, and perspectives. Susan Jones was trying to collaborate for the good of "the whole," but she forgot that there isn't just one whole. The nurses' whole is different from the surgeons' whole, which is different from the administrators' whole. Jackson: Okay, I see. By forcing harmony in that one room, she created discord everywhere else. She was trying to draw a perfectly straight line on a crumpled piece of paper. Olivia: That’s a perfect way to put it. Kahane argues this constricted approach only works for simple, technical problems. But for complex, human problems—what he calls "wicked problems"—it’s a recipe for failure. You can't control the outcome, and you can't force genuine agreement. Jackson: This is already making me rethink every team meeting I've ever led. If the neat, orderly planning meeting is broken, what’s the alternative? Just letting chaos reign?

Olivia: That’s the million-dollar question, and Kahane’s answer is fascinating. He says the alternative isn't chaos. It's something that looks less like a planning meeting and more like martial arts practice. It’s messy, it’s responsive, and it’s co-created in the moment. He calls it "stretch collaboration." Jackson: Martial arts practice? Okay, you have my attention. Is this where the trust falls come back in? Olivia: Not quite. It’s about three fundamental "stretches" that go against our natural instincts. The first is to embrace conflict and connection. You have to be willing to fight for your position but also stay connected to the people you're fighting with. He calls this balancing "power," our drive to self-actualize, and "love," our drive to unite. Jackson: Power and love. That sounds a little… new-agey for a business book. Olivia: It does, but he grounds it in very practical terms. Power without love is just abuse. Love without power is sentimental and weak. You need both. The second stretch is to experiment a way forward. Instead of a rigid plan, you take a step, see what happens, and adjust. He quotes a Chinese proverb: "We are crossing the river by feeling for stones." Jackson: I like that. It’s less about having a perfect map and more about everyone agreeing to explore the territory together, even if they have different ideas about the destination. What’s the third stretch? Olivia: The third is "step into the game," which we’ll get to because it’s the hardest one. But first, let me tell you where this all comes together. The story of the Destino Colombia project is one of the most powerful examples of stretch collaboration I’ve ever read. Jackson: The country with a decades-long civil war? That seems like the ultimate test case. Olivia: The ultimate. In the mid-90s, Colombia was in chaos. You had the government, multiple guerrilla armies, paramilitary groups, drug traffickers—all locked in a cycle of violence. A young politician named Juan Manuel Santos, who would later win the Nobel Peace Prize, was inspired by a similar project Kahane had facilitated in post-apartheid South Africa. He decided to try something radical. Jackson: What did he do? Olivia: He invited leaders from all sides—including sworn enemies—to a series of workshops. We're talking military generals sitting at the same table as guerrilla commanders, business leaders with leftist activists. The goal was not to create a peace treaty. That would have been impossible. Jackson: So what was the goal? Olivia: The goal was simply to create stories—scenarios—of what Colombia's future could look like. They weren't trying to agree on the problem or the solution. They were just trying to map out the possibilities together. It was incredibly tense. At one point, a notorious paramilitary leader, Carlos Castaño, was participating by speakerphone from his jungle hideout. Jackson: You're kidding. That's unbelievable. Olivia: It gets better. During one session, a communist party leader, Jaime Caicedo, was at the table. His life had been threatened multiple times by Castaño's group. Another paramilitary leader in the room, Iván Duque, stood up and, in front of everyone, pleaded with his comrades to spare Caicedo's life. He said, "We are building something new here." In that moment, they weren't enemies. They were collaborators, stretching toward a different future. Jackson: Wow. So they made progress without even agreeing on the past, let alone a plan for the future. How is that even possible? Olivia: Because they gave up the illusion of control. They embraced the conflict in the room, but they also stayed connected as human beings. They experimented with ideas. And that process, Kahane says, fundamentally changed the national conversation. It created a "before" and an "after." It made peace imaginable. Jackson: That’s incredible. It completely reframes what collaboration is. It’s not about finding the right answer. It’s about creating the conditions for a new answer to emerge. Olivia: Exactly. And that brings us to the third and, honestly, the most difficult stretch. Because it's easy to talk about changing systems and getting enemies to talk. But Kahane argues you can’t be part of the solution if you don't first see how you’re part of the problem.

Jackson: Oof. That hits close to home. It’s so much easier to point fingers and say, "The problem is them! If they would just change, everything would be fine." Olivia: We all do it. It's human nature. Kahane quotes the old Pogo comic strip: "We have met the enemy and he is us." This third stretch, "stepping into the game," is about shifting your focus from trying to change others to being willing to change yourself. And he learned this lesson the hard way. Jackson: Through another one of his projects? Olivia: Yes, and he’s incredibly vulnerable in sharing this story. He was leading a huge, ambitious project in India called the Bhavishya Alliance, aimed at reducing child malnutrition. It involved 26 different organizations—government, NGOs, multinational corporations. The pressure was immense. Jackson: Sounds like a recipe for conventional collaboration to fail. Olivia: And it did. As the deadline approached and things got messy, Kahane found himself becoming more controlling, more directive, more certain that he knew best. He was trying to force a solution. When the team presented their final proposals, the heads of the organizations tore them apart. The project was a massive failure. Jackson: Oh, man. That must have been crushing for a world-renowned facilitator. Olivia: He was humiliated and angry. For months, he blamed everyone else: the stubborn bureaucrats, the clueless executives. He was stuck. Then, he came across a quote from the philosopher Martin Buber that changed everything. It said, "The essential thing is to begin with oneself." Jackson: And he realized he had been part of the problem. Olivia: He realized he was the one who had been constricting the collaboration with his own need for control. He hadn't stepped into the game; he'd tried to stand outside it and direct it. It’s a profound shift. It’s the difference between being involved and being committed. Kahane uses this brilliant little joke to explain it. Jackson: I’m ready. Lay it on me. Olivia: In a ham omelet, the chicken is involved, but the pig is committed. Jackson: [Laughs] Okay, that’s dark, but I get it. The chicken gives something, but the pig gives everything. To truly collaborate in these tough situations, you have to be the pig. You have to have skin in the game. Olivia: You have to be willing to sacrifice your own certainty, your own comfort, your own ego. And that is the hardest stretch of all.

Jackson: You know, as we talk through this, I realize the title, Collaborating with the Enemy, is almost a misdirection. The book isn't really about them—the enemy. It feels like a Trojan horse for a book about confronting the enemy in ourselves. Olivia: That’s such a great insight. It absolutely is. It’s about our own need for control, our deep-seated fear of conflict, and our absolute certainty that we are the reasonable ones. Jackson: And that’s what makes the ideas so challenging. The book has a bit of a mixed reception online. It’s praised for being profound, but some readers find it difficult or even unrealistic because it doesn't offer easy answers. It demands that you do the hard work on yourself first. Olivia: It really does. And Kahane leaves us with this powerful final metaphor from the world of Tai Chi to drive that point home. A Tai Chi master says that when you're practicing push hands with an opponent, "No matter how hard and unyielding your opponent, our inability to deal gently with him is indicative of our own stuckness." Jackson: Wow. So if I’m struggling with a difficult colleague, it’s not because they’re a jerk. It’s because their jerkiness is revealing a place where I’m rigid and stuck. Olivia: Exactly. The opponent is just a teacher. Their resistance is a gift, showing you where you need to stretch. The real game is with yourself. Jackson: That completely changes how I think about every difficult person in my life. They’re not obstacles; they’re opportunities for me to find and dissolve my own stuckness. Olivia: It’s a powerful reframe. So the question for all of us listening is, in that one collaboration that's driving you crazy right now—at work, in your family, in your community—what "stuckness" in you is your "enemy" trying to teach you? Jackson: That is a question I’m going to be thinking about for a long time. We'd love to hear your thoughts on this. Find us on our socials and share one situation where you realized you were part of the problem. Let's get this conversation started. Olivia: This is Aibrary, signing off.