Collaborating with the Enemy

Picture this: You're sitting across the table from someone who fundamentally disagrees with everything you believe in. Their values clash with yours, their approach feels wrong, and frankly, you'd rather be anywhere else. Yet here you are, tasked with finding a way forward together. Sound familiar? Welcome to the reality of modern collaboration.

In today's interconnected world, we can no longer afford the luxury of working only with people who think like us. Whether you're navigating office politics, family dynamics, community issues, or global challenges, success increasingly depends on your ability to collaborate with people you don't agree with, don't particularly like, or don't fully trust. The old approach of seeking harmony and consensus simply isn't enough anymore. We need a new playbook for working with our so-called enemies.

The first step toward effective collaboration isn't learning how to work with difficult people—it's understanding when you should even try. Collaboration isn't always the answer, and recognizing this can save you tremendous time and energy.

Consider the framework of four fundamental approaches to any challenging situation. You can force your way through by imposing your will on others. You can adapt by accepting the situation as it is and working within existing constraints. You can exit by removing yourself entirely. Or you can collaborate by working together to create something new. Each option has its place, and choosing the wrong one can lead to frustration and failure.

Take the example from Thailand, where political leaders faced violent protests and deepening divisions. Some chose the forcing approach, trying to impose their vision on opponents. Others adapted, accepting the status quo and working around it. Still others exited the political process altogether. But a small group chose collaboration, bringing together sworn enemies to explore new possibilities for their country's future. Their work didn't solve everything overnight, but it planted seeds that would eventually bloom into meaningful change.

The key insight is this: collaboration becomes your best option when you cannot achieve your goals alone, when forcing your way isn't feasible, when adapting feels insufficient, and when exiting isn't desirable. It's a choice born of both necessity and opportunity. When you recognize these conditions, you're ready to embrace the challenge of working with unlikely partners.

Remember, choosing collaboration doesn't mean giving up your principles or compromising your values. It means recognizing that your most important goals might only be achievable by joining forces with people who see the world differently. This realization can be both humbling and empowering, marking the beginning of your journey toward more effective collaboration.

Traditional collaboration assumes everyone wants the same thing and can work harmoniously toward shared goals. This fairy-tale version rarely survives contact with reality. Real collaboration—what we might call "stretch collaboration"—requires three fundamental shifts that challenge everything you think you know about working with others.

The Mont Fleur project in South Africa provides a powerful example of these stretches in action. In the early 1990s, as apartheid was ending, a diverse group of South Africans came together to envision their country's future. The team included politicians from opposing parties, business leaders, activists, academics, and community organizers. These weren't people who naturally got along—many had been enemies for decades.

What made their collaboration successful wasn't the elimination of conflict or the discovery of perfect consensus. Instead, they learned to embrace three essential stretches that transformed how they worked together. First, they embraced both conflict and connection, allowing disagreements to surface while maintaining their commitment to the collective effort. Second, they experimented their way forward, creating multiple scenarios rather than trying to agree on one perfect plan. Third, each participant stepped fully into the process, willing to be changed by the experience rather than simply trying to change others.

These three stretches form the foundation of effective collaboration with difficult people. They require you to abandon comfortable assumptions about how groups should work and embrace a more dynamic, unpredictable, and ultimately more powerful way of creating change together. Each stretch challenges you to move beyond your comfort zone, but the results can be transformational—both for your projects and for you personally.

The first stretch might seem counterintuitive: instead of avoiding conflict, you must learn to embrace it alongside connection. Most people believe good collaboration means getting along, finding common ground, and maintaining harmony. This conventional wisdom isn't just wrong—it's dangerous. When you suppress conflict in favor of artificial harmony, you create the conditions for manipulation and stagnation.

Consider the story of Clara Arenas, a Guatemalan activist who shocked a gathering of well-meaning dialogues by taking out a newspaper advertisement declaring she would no longer participate in collaborative processes. Her reason? The government expected that organizations participating in dialogue would stop organizing strikes, marches, and other forms of resistance. Arenas understood something crucial: if you can't assert your position forcefully when needed, your engagement becomes meaningless.

The key lies in understanding that every person and organization has two fundamental drives. The drive for power seeks self-realization and expression—it's what makes you stand up for what matters to you. The drive for love seeks unity and connection—it's what draws you toward others and larger purposes. Both drives are essential, and problems arise when you overuse one while neglecting the other.

Effective collaboration requires you to alternate between these drives like breathing in and out. Sometimes you need to assert your position firmly, even if it creates tension. Other times you need to engage empathetically, seeking to understand and connect with others. The art lies in sensing when each is needed and having the courage to make the shift. When someone feels they're being asked to compromise too much, it's time for assertion. When positions become too rigid and confrontational, it's time for engagement.

This dance between conflict and connection isn't about finding perfect balance—it's about staying responsive to what the situation requires. Master this rhythm, and you'll find that your collaborations become more honest, more creative, and ultimately more effective.

The second stretch challenges another fundamental assumption: that successful collaboration requires agreement on the problem, the solution, and the plan. In complex situations with diverse stakeholders, such agreements are often impossible to reach and unnecessary to achieve. Instead, you must learn to experiment your way forward through uncertainty.

The drug policy project in the Americas illustrates this approach beautifully. For forty years, governments had pursued a single strategy—the "war on drugs"—with limited success. When Colombian President Juan Manuel Santos called for new thinking, it led to an unprecedented collaboration between government officials and reform activists who had been enemies for decades. These groups couldn't agree on what the problem was, let alone what the solution should be.

Rather than forcing consensus, the project team created four different scenarios describing possible futures for drug policy in the region. They didn't advocate for any particular approach but instead opened up space for experimentation and learning. This approach allowed participants with radically different worldviews to contribute their perspectives without having to abandon their core beliefs. The result was a breakthrough in thinking that influenced policy discussions across the hemisphere.

This experimental approach requires what poet John Keats called "negative capability"—the ability to remain in uncertainty and doubt without irritably reaching after facts and answers. Like an artist working on a canvas, you must be willing to try something, observe the results, and then adjust based on what you learn. This means holding your plans lightly, being willing to destroy beautiful ideas that aren't working, and staying open to possibilities you couldn't have imagined at the start.

The most powerful collaborations emerge not from perfect planning but from skillful improvisation. By experimenting together, you and your unlikely partners can discover solutions that none of you could have invented alone. This requires courage, patience, and a willingness to look foolish occasionally—but the breakthroughs make it worthwhile.

The third stretch might be the most challenging: shifting from trying to change others to being willing to change yourself. Most people approach collaboration with a simple question: "How can we get them to do what needs to be done?" This question reveals a fundamental misunderstanding about how change actually works in complex situations.

The Bhavishya Alliance in India, which brought together twenty-six organizations to address child malnutrition, provides a sobering example of what happens when leaders focus on changing others rather than themselves. Despite careful planning and good intentions, the initial phase ended in disappointment when senior executives rejected most of the team's proposals. The failure wasn't due to lack of expertise or effort—it stemmed from participants' reluctance to examine their own roles in perpetuating the problems they were trying to solve.

The breakthrough came when participants realized that if they weren't part of the problem, they couldn't be part of the solution. This insight requires a fundamental shift in perspective—from seeing yourself as outside the situation trying to fix it, to recognizing yourself as within the situation helping to create it. When you make this shift, you discover that you have far more power to influence outcomes than you imagined.

Stepping into the game means abandoning the comfortable illusion that problems are caused by other people's failures and solutions require other people's changes. Instead, you ask yourself: "What am I doing that contributes to this situation being the way it is? What do I need to do differently for things to change?" These questions can be uncomfortable, but they're also liberating because they put power back in your hands.

This doesn't mean you become a doormat or stop advocating for what you believe in. Rather, you become more strategic and effective by focusing your energy where you have the most control—on your own actions and responses. When you model the changes you want to see, you often inspire others to do the same. But even when they don't, you're still making progress because you're changing the part of the system you have the most influence over: yourself.

Working with people you disagree with, dislike, or distrust isn't just a nice-to-have skill in today's world—it's essential for anyone who wants to tackle meaningful challenges. The three stretches of effective collaboration offer a roadmap for navigating these difficult relationships while staying true to your values and achieving your goals.

As one wise observer noted, "We have met the enemy and he is us." This insight captures the essence of what makes collaboration so challenging and so powerful. Your greatest obstacles often aren't the difficult people across the table—they're your own assumptions, habits, and fears about what's possible when different perspectives collide. When you learn to work with both the enemies outside and the resistance within, you unlock tremendous potential for creating positive change.

The path forward is clear: start where you are, with the people and challenges in front of you. Choose one relationship or situation where collaboration could make a difference, then practice these stretches. Embrace the conflict that arises rather than smoothing it over. Experiment with small steps instead of demanding perfect plans. Focus on changing your own contribution to the dynamic rather than waiting for others to change theirs. Your enemies might just become your greatest teachers—and your most unexpected allies in creating the change the world needs.