Collaborating with the Enemy

Adam Kahane

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Collaborating with the Enemy
By Adam Kahane

Summary Snapshot

In "Collaborating with the Enemy," Adam Kahane explains that it's important to work with people you don't agree with in today's complicated world. He talks about "stretch collaboration," which means accepting disagreements, trying out new ideas, and focusing on changing your own actions rather than others'. By sharing your opinions while also connecting with others, trying out solutions gradually, and changing your own behavior, you can turn disagreements into creative teamwork, even if there's no trust.

“Dive deeper in 30: See if this book clicks with you in our key takeaways.”

  • Understand Stretch Collaboration
    Stretch collaboration means working with people you may not agree with, like, or trust. It is different from traditional teamwork where everyone seeks harmony. When you stretch collaborate, you accept conflict, experiment with solutions, and focus on your own role. This helps groups navigate uncertainty by allowing real issues to surface, rather than forcing false unity.

  • Avoid Forced Harmony
    In many projects, people try to suppress disagreements to appear united. Kahane warns that forced harmony can cause hidden tensions that later erupt. Instead of hiding conflict, you should acknowledge differences openly. When disagreements are out in the open, you can deal with them honestly and find new ways forward together, without pretending everything is fine.

  • Accept That Plans Must Change
    Conventional methods often demand a detailed plan before taking action. In complex situations, this does not work because people cannot agree on all details and conditions keep changing. Kahane teaches you to start with multiple ideas and try them in real life. As you learn what works, you refine your approach. This way, plans evolve rather than break under pressure.

  • Focus on Your Own Behavior
    You cannot control how others act, but you can control your own contributions. When you shift your attention to how you behave, your actions can influence the group’s dynamics. By making small changes, listening more attentively, and speaking with genuine curiosity, you create space for others to respond differently. This ripple effect can change the whole system more effectively than trying to force others to change first.

  • Balance Power and Love
    People have two drives: the drive for power, which pushes for self-interest, and the drive for love, which seeks connection. If you focus too much on power, you create division. If you focus only on love, you hide important differences. Stretch collaboration asks you to alternate between these drives. Sometimes you must assert your needs, and other times you must listen and connect.

  • Embrace Conflict’s Positive Side
    Conflict often feels negative, but Kahane explains that conflict can spark creativity when managed well. When people with different ideas engage honestly, they can uncover new solutions that no one person could have imagined alone. Instead of pushing conflict away, welcome it as a source of fresh thinking. Work through tensions together to discover better paths forward.

  • Build Genuine Connections
    Collaboration succeeds when people trust each other. Genuine connections form when you listen, share personal stories, and show respect. Even if you disagree, finding shared values or experiences helps build trust. As trust grows, people feel safe speaking openly about their concerns, making collaboration possible even among those who initially began as adversaries.

  • Alternate Between Asserting and Listening
    Effective collaborators know when to speak up and when to step back. If you always push your ideas, others shut down. If you only listen, important issues remain unspoken. Kahane recommends shifting from making strong statements to asking questions that invite others to share their thoughts. This dance between speaking and listening helps maintain balance between conflict and connection.

  • Focus on Small Experiments
    In complex situations, it is impossible to know what will work until you try. Instead of debating endlessly, design small tests or pilots. For example, create a short prototype or run a narrow trial to see how people react. Use the feedback to learn and adapt. Each experiment teaches you something new and guides you toward solutions that actually work.

  • Learn Quickly from Feedback
    After testing ideas, gather feedback without blaming anyone. Look at what succeeded and what failed. Ask questions like “What surprised us?” or “What obstacles did we face?” Use honest reflection to change your approach. By valuing learning over being right, you keep the process moving. Every setback becomes a chance to discover a better way.

  • Keep Multiple Possibilities Open
    When people insist on a single fixed plan, they overlook other options. Instead, generate a range of possible solutions and share them with the group. Discuss pros and cons without rushing to choose. This openness allows creativity to flourish. As you test various ideas, some options will prove more viable, guiding the group toward the best path without forcing everyone into a premature agreement.

  • Accept Emergence over Certainty
    Complex challenges do not yield to top-down control. Instead of trying to predict every detail, accept that the way forward will appear gradually. By engaging in joint action and observing results, you allow new directions to emerge organically. This emergent process may feel uncertain, but it reflects reality more accurately than rigid plans. Trust that learning together will reveal the next step.

  • Recognize Your Own Biases
    You see the world through your own experiences and beliefs. In collaboration, you must question your assumptions about others’ motives and needs. Ask yourself why you interpret someone’s action in a certain way. By uncovering hidden biases, you avoid misjudging others and causing unnecessary conflict. Admitting biases leads to more open and honest engagement.

  • Practice Dialoguing Instead of Debating
    Debating means arguing over facts and winning points. Dialoguing means sharing your feelings and listening to others’ emotions and values. In stretch collaboration, shift from debating to dialoguing. Speak from your own experience and ask others to do the same. This builds empathy and uncovers the reasons behind people’s positions, fostering deeper understanding.

  • Engage in Presencing
    Presencing requires listening for what the group as a whole is sensing, beyond individual viewpoints. It is like tuning into a collective insight that arises from the group’s combined experience. When you practice presencing, you open space for innovative ideas that no single person could create. It requires stillness, attention, and the willingness to embrace uncertainty.

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  • Hold Multiple Perspectives Simultaneously
    In complex problems, different people see different truths. Instead of forcing one perspective to win, hold several viewpoints at once. Create a space where each viewpoint is respected. By weaving these perspectives together, you can develop richer solutions that address various concerns. This skill requires practice but leads to stronger, more inclusive outcomes.

  • Use Stories to Build Shared Meaning
    Facts alone rarely unite people. Sharing personal stories about why issues matter to you helps others understand your perspective. When people relate through storytelling, they see common values and emotional connections emerge. These shared narratives form a foundation of mutual respect, making it easier to navigate disagreements and find creative solutions.

  • Change Your Role Instead of Blaming Others
    When collaboration stalls, it is tempting to blame others for not listening or cooperating. Kahane advises turning that impulse inward. Ask how your own actions might contribute to the problem. By changing how you participate, speaking more clearly, and listening more deeply, you shift the dynamic. Others are likely to respond in kind, breaking the cycle of blame and opening up new possibilities.

  • Develop Self-Awareness for Better Collaboration
    Pay attention to how you react in tense moments: Do you shut down, become defensive, or push too hard? Noticing these patterns is the first step toward change. Utilize self-reflection practices, such as journaling, meditation, or feedback from trusted colleagues, to become aware of your habits. As you gain insight, you can experiment with new behaviors that foster more productive collaboration.

  • Create Support Systems for Change
    Changing ingrained habits is hard. To succeed, surround yourself with people who can support and remind you of your goals. Ask a colleague to give you honest feedback when you fall back into old habits. Use visual reminders, like notes on your computer, to prompt new behaviors. These supports help you stay on track and celebrate small improvements.

  • Build Trust through Small Acts
    Trust does not appear overnight. It grows when people consistently act with integrity, follow through on promises, and show genuine concern. In each interaction, make small commitments, listen carefully, follow up promptly, and be courteous. These small acts signal reliability and make others more willing to take risks with you, even when differences exist.

  • Use Feedback as a Tool for Growth
    Ask for and welcome feedback on your collaboration style. When someone highlights a blind spot, listen without getting defensive. Treat feedback as information about how you can improve rather than a personal attack. By showing that you value others’ perspectives, you strengthen relationships and model openness, encouraging others to do the same.

  • Face Emotional Reactions Directly
    Conflict often produces strong emotions, including frustration, anger, or fear. Instead of ignoring these feelings, acknowledge them. Name the emotion (“I feel frustrated”). When you express your feelings without blaming, you create an opportunity for others to respond with empathy. This emotional honesty reduces misunderstandings and builds a connection even amid disagreement.

  • Design Iterations with Clear Indicators
    When you test ideas, decide in advance what success looks like. Use simple metrics or observations to track progress, like attendance at a pilot event, level of engagement, or quality of feedback. Clear indicators help you know which experiments to scale up and which to adjust. This clarity keeps the group aligned and focused on learning.

  • Be Prepared to Pivot
    If an experiment fails or yields unexpected results, do not see it as a defeat. Instead, view it as information pointing you toward a new path. Quickly regroup, reassess assumptions, and design the next experiment. This agility means you do not get stuck in failing plans. By pivoting based on real-time feedback, you steer collaboration toward what actually works.

  • Embrace Uncertainty as Part of the Process
    Working with adversaries means you cannot predict everything. Instead of fearing uncertainty, recognize it as fertile ground for discovery. Stay open-minded and curious. When you let go of the need for full control, you become more flexible and responsive. Uncertainty becomes an ally that keeps you attentive to new information and ready to adapt.

  • Honor Each Participant’s Perspective
    In complex collaborations, each person represents a broader group, such as an organization, community, or viewpoint. Respect that each perspective is valid. Avoid treating any single viewpoint as more important than the others. By giving each participant space to speak and be heard, you create a sense of fairness that encourages ongoing participation even when conflicts arise.

  • Leverage Collective Intelligence
    The group’s wisdom often exceeds what any individual can offer. Make space for everyone to contribute ideas, even if they seem unusual. Use brainstorming sessions or inclusive workshops where no idea is dismissed initially. By gathering diverse insights, you increase the chances of finding innovative solutions that meet multiple needs.

  • Use Real-World Examples to Inspire Change
    Stories of successful stretch collaboration illustrate what is possible. For instance, neighborhood groups that combined different visions into a shared community space show how acknowledging conflict can lead to creative solutions. Such examples encourage people to try new ways of working. When participants see real cases, they feel more confident experimenting with stretch collaboration in their own context.

  • Commit to Continuous Learning
    Stretch collaboration is not a one-time fix. It is an ongoing practice that evolves as situations change. Dedicate to revisiting your methods, reflecting on outcomes, and refining your approach. Celebrate successes and learn from setbacks. By treating collaboration as a continuous learning journey, you build resilience to face future challenges with confidence and creativity.

What’s Next?

Identify one difficult relationship you have at work or in your community. Invite that person to a brief discussion focused on shared values. In that meeting, listen deeply to their concerns and share your own with honesty. Agree to try a small joint experiment, then meet again to learn and adjust.

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