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Collaborating with the Enemy

10 min

How to Work with People You Don’t Agree with or Like or Trust

Introduction

Narrator: Imagine a country torn apart by a fifty-year civil war. The players are not just politicians; they are guerrilla armies, paramilitary groups, drug traffickers, and military generals. They are sworn enemies who have tried to kill one another, whose ideologies are fundamentally opposed, and whose distrust runs deeper than memory. Now, imagine trying to get these people in the same room, not to surrender or negotiate a truce, but to collaborate on creating a shared future. It seems both essential for survival and utterly impossible.

This is the exact scenario that Adam Kahane confronts in his book, Collaborating with the Enemy: How to Work with People You Don’t Agree with or Like or Trust. He argues that our most complex and urgent problems—from political polarization to climate change to internal corporate dysfunction—require us to work with the very people we consider adversaries. The book dismantles our traditional ideas about teamwork and offers a radical, more realistic path forward for when harmony is a fantasy and control is an illusion.

Conventional Collaboration Is a Dead End

Key Insight 1

Narrator: The traditional model of collaboration is fundamentally broken for complex problems. Kahane argues that we typically envision collaboration as a neat and orderly planning meeting. A group of people get together, agree on a common goal, create a detailed plan, and then execute it. This approach, which he calls "constricted collaboration," rests on a dangerous assumption: that the situation is controllable and that everyone can, and should, align around a single right answer.

This model fails spectacularly in the face of messy, real-world challenges. Consider the story of Susan Jones, the CEO of a large hospital facing poor clinical and financial results. She did everything right according to the conventional playbook. She hired expert consultants, formed a team of her top managers, and developed a comprehensive transformation plan. The team reached a consensus, and Jones announced the rollout with confidence. The result? The hospital staff met the plan with cynicism and resistance. Implementation was plagued by delays and complications, and the hospital's performance actually worsened. The project was a failure because it tried to impose a single, top-down solution on a complex system of people with diverse, and often conflicting, interests and perspectives. The "good of the whole" ignored the realities of the many parts.

Stretch Collaboration Embraces the Mess

Key Insight 2

Narrator: If the orderly planning meeting is the wrong model, what’s the right one? Kahane proposes an alternative he calls "stretch collaboration." Instead of a planning meeting, he says, we should picture a martial arts practice. In martial arts, you don’t have a predetermined script. You engage with your partner, responding to their moves, experimenting with your own, and co-creating the flow of the interaction. You embrace the unpredictable nature of the encounter.

Stretch collaboration does the same. It abandons the illusion of control and accepts that in complex situations, we cannot agree on the problem, the solution, or the plan. The goal is not to create a perfect roadmap but to move forward together. A powerful example of this is the Mont Fleur Scenario Exercise in South Africa in the early 1990s. As the country teetered on the brink of civil war during the transition from apartheid, leaders from all sides—the white establishment, the African National Congress, trade unions, and business—came together. They didn't try to agree on a single vision. Instead, they collaborated to create four different stories, or scenarios, of what South Africa's future could look like. This process allowed them to understand each other's hopes and fears and to navigate the transition without having a single, unified plan. They made the path by walking it together.

The First Stretch - Balance Power and Love

Key Insight 3

Narrator: To practice stretch collaboration, we must first learn to embrace both conflict and connection. Conventional collaboration often overemphasizes harmony, dialogue, and finding common ground. Kahane argues this is only half the equation. He introduces two fundamental human drives, drawn from the work of Martin Luther King Jr.: Power and Love. Power is the drive to assert ourselves, to achieve our goals, and to realize our own potential. Love is the drive to unite, to connect with others, and to be part of a larger whole.

Effective collaboration requires us to balance and alternate between these two drives. Power without love is reckless and abusive, while love without power is sentimental and anemic. Nelson Mandela is a prime example of this balance. We often remember him as the great reconciler who engaged in dialogue with his enemies. But we forget that he was also a fighter who co-founded the armed wing of the ANC and asserted his people's demands relentlessly. He knew when to fight and when to talk. This first stretch requires us to stop seeing collaboration as just being nice and to recognize that sometimes, to move forward, we must assert our own interests and engage in constructive conflict.

The Second Stretch - Experiment to Find the Path

Key Insight 4

Narrator: The second stretch is to abandon the need for a perfect, pre-approved plan and instead experiment our way forward. In complex situations, the future is unknowable. As the poet Antonio Machado wrote, "Walker, there is no path. The path is made by walking." This means taking a step, observing what happens, learning from it, and then deciding on the next step.

This was the core of a project on drug policy in the Americas, facilitated by the Organization of American States (OAS). For decades, the "war on drugs" had been a costly failure, yet the system was stuck. The project brought together forty-six leaders from across the hemisphere who held deeply opposing views. Instead of trying to force an agreement on a new policy, they experimented. They created scenarios of different possible futures for the drug problem. This process didn't produce a single solution, but it broke the gridlock. It opened up the conversation to new possibilities and allowed a system that had been stuck for forty years to finally start moving. They didn't know the destination, but by experimenting, they found a way to take the next step.

The Third Stretch - Step into the Game and Change Yourself

Key Insight 5

Narrator: The final and most difficult stretch is to shift our focus from trying to change others to being willing to change ourselves. In any conflict or dysfunctional situation, our natural tendency is to blame. We see others as the problem. As the cartoon character Pogo famously said, "We have met the enemy and he is us." Stretch collaboration requires us to recognize that if we are part of a situation, we are also part of the problem.

Kahane shares a painful personal story from his work on the Bhavishya Alliance in India, a project aimed at reducing child malnutrition. When the project’s proposals were rejected by senior leaders, Kahane’s immediate reaction was to feel humiliated and to blame the leaders for their shortsightedness. It was only months later, after encountering the work of philosopher Martin Buber, that he had a crucial realization: his own controlling, top-down behavior during the project had contributed to its failure. He had been focused on what they needed to do differently, not on what he needed to do differently. Stepping into the game means accepting our own role in creating the reality we want to change and understanding that the only person we can truly control is ourselves.

Conclusion

Narrator: The single most important takeaway from Collaborating with the Enemy is that meaningful progress on our toughest challenges doesn't come from getting other people to change. It comes from having the courage to change ourselves. It requires us to abandon the comfortable position of being an observer who critiques from the sidelines and to step fully into the game, acknowledging our own contribution to the problem.

This leads to the book's most challenging and profound final thought: your enemies can be your greatest teachers. The people we disagree with, dislike, or distrust are not just obstacles to be overcome. Their resistance, their opposition, and their different perspectives are precisely what force us to look in the mirror, to question our own assumptions, and to "stretch" beyond our current limitations. The ultimate challenge, then, is not to defeat the enemy, but to learn from them how to become a better version of ourselves.

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