PDF Summary:Collaborating with the Enemy, by Adam Kahane

Have you ever found yourself stuck in a project with people you don’t agree with, like, or trust? In Collaborating with the Enemy, conflict resolution expert Adam Kahane draws on his experience mediating high-stakes conflicts—from post-apartheid South Africa to corporate boardrooms—to offer an unconventional approach to working with difficult collaborators. Kahane’s “stretch collaboration” framework shows how to embrace both conflict and connection, experiment with different solutions when the path ahead isn’t clear, and focus on changing your contribution rather than trying to change others.

In our guide, you’ll learn strategies for transforming seemingly impossible collaborations into productive partnerships without requiring artificial harmony or universal agreement. We’ll also explore how these principles apply across different contexts—from community organizing to couture ateliers—and how they connect to Buddhism and its imperative to transcend your own perspective. Master these techniques and you’ll never again feel powerless when faced with collaborating with your “enemies.”

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3) Practice alternating between asserting and engaging. When the group is stuck in conflict, intentionally shift toward connection. When artificial harmony prevails, deliberately bring tensions to the surface. Pay attention to which drive (power or love) you tend to overuse, and consciously balance it.

4) Recognize that each participant represents their own “whole” (organization, community, or perspective). Avoid privileging any single whole as more important than others. Create space for multiple perspectives to interact without requiring them to merge.

(Shortform note: In an example from pop culture, the relationship between Godzilla and Mothra across decades of films illustrates Kahane’s principles for balancing conflict and connection. Initially introduced as adversaries in 1964, Mothra and Godzilla move fluidly between conflict (asserting their distinct perspectives) and cooperation (engaging with each other for mutual benefit). In recent films, Mothra serves as a mediator who interrupts Godzilla’s destructive rampages and redirects his attention toward greater threats. Their relationship also shows how collaborators can maintain distinct identities: Neither monster surrenders their nature to work together. Godzilla remains chaotic and powerful, while Mothra is protective and benevolent.)

For a real-world example of Kahane’s first principle in action, imagine a suburban neighborhood committee that’s divided over development plans: some want a traditional park with a bandstand, others want a modern recreation center, and a third group advocates for a shopping plaza. Rather than forcing consensus, they convene at the community hall where each faction explains their priorities—preserving green space, providing youth activities, and bringing convenience to the growing suburb.

When discussions grow heated, the committee chairman suggests they identify shared values across groups. A typically outspoken business owner practices listening more attentively, while a normally reserved schoolteacher speaks up when the conversation veers toward a superficial agreement. Their breakthrough comes when they recognize that each group represents legitimate community interests. Instead of selecting just one vision, they develop a comprehensive plan incorporating a central green with a bandstand flanked by a youth recreation building and a small row of shops—acknowledging that different needs can coexist in a thoughtfully designed community space.

Principle #2: Try an Adaptive, Iterative Approach

Kahane explains that stretch collaboration requires abandoning the illusion of control through detailed planning and instead allowing solutions to emerge through action and learning. Conventional collaboration assumes we can agree on a detailed plan before taking action, but this assumption fails in complex situations for several reasons: First, no one actually knows what will work until it’s tried. Second, different people have different ideas about what should happen. Third, situations are constantly evolving, making static plans quickly obsolete. And perhaps most importantly, possibilities that couldn’t be anticipated in the planning stage often emerge when putting plans into action.

Instead of trying to control the future through planning, stretch collaboration involves systematically experimenting with different possibilities and adapting based on what you learn. This approach recognizes that in complex situations, the way forward can only be discovered by walking it.

(Shortform note: While Kahane emphasizes abandoning detailed plans, French clothing design workshops reveal a key nuance: Creative experimentation often requires more structure, not less. In these workshops, rigorous systems support the experimental process—clear hierarchies among craftspeople, specialized divisions of labor, and methodical stages like creating designs before final garments. But within this framework, the actual interpretation of designer sketches remains highly experimental. This suggests that collaborators might focus less on eliminating planning and more on making the right kinds of plans—ones that establish boundaries, resources, and rhythms for experimentation while preserving freedom within those parameters.)

Practical Steps to Taking an Experimental Approach

Effective adaptation requires you to move beyond your default ways of communicating. Kahane identifies four modes of talking and listening: “Downloading” involves speaking from within your perspective and listening for confirmation of what you believe. “Debating” entails speaking objectively about facts and listening to judge if they’re correct. “Dialoguing” means speaking from self-reflection and listening with empathy to others’ experiences. “Presencing” involves speaking from an emerging collective perception and listening to the system as a whole. Kahane notes most conversations get stuck in downloading and debating, but to create new possibilities, you also need to engage in dialoguing and presencing.

(Shortform note: The brain processes Kahane’s communication modes in different ways. When “downloading,” we use the prefrontal cortex: the brain’s planning and self-reference center. In “debating,” similar regions activate, along with motor areas, reflecting our evaluative stance. Shifting to “dialoguing” engages regions like the temporoparietal junction, which specializes in understanding others’ perspectives. “Presencing” requires coordination across multiple brain networks and involves the anterior cingulate cortex, which integrates various social signals. This might explain why some conversations get stuck in downloading or debating: Those modes are simply easier for our brains and require less coordination between specialized networks.)

To implement an adaptive, iterative approach to collaborative work, Kahane advises that you:

1) Articulate multiple possibilities rather than a single plan. Begin with a wider scope of what might be possible, encourage different stakeholders to contribute their ideas, and resist prematurely narrowing the group’s options to reach a consensus.

2) Test assumptions through small-scale trials. Identify the key assumptions underlying the different possibilities you’re considering, then design low-cost, low-risk experiments to test those assumptions, using prototypes and pilot projects to speed up the learning process.

3) Create rapid feedback loops. Establish clear indicators to track the effects of your group’s experiments, schedule regular reflection points to assess what’s being learned, and be willing to adapt or abandon approaches based on the feedback you get.

4) Pay attention to unexpected developments and unintended consequences. Look for creative possibilities that weren’t part of the group’s original thinking. Allow the way forward to emerge from the group’s collective intelligence rather than forcing it to conform to a plan.

5) Maintain a learning mindset throughout the process. Treat “failures” as valuable information rather than setbacks. Ask “What can we learn from this?” rather than “Who is to blame?” Celebrate insights and adaptations, not just successful outcomes.

For example, imagine that a World’s Fair exhibition committee is deadlocked over their pavilion theme. Initially, members are entrenched in their positions (“We should showcase industrial achievements” versus “We should highlight cultural heritage”) and debating attendance projections from previous expositions. The committee chairman could redirect the conversation by having each person share their most memorable exhibition experience and why it mattered.

Instead of forcing agreement on one concept, the committee might generate multiple possibilities and test them with models and public previews, such as a manufacturing demonstration, a traditional crafts display, and an audiovisual presentation of their city’s history. With visitor response cards and weekly evaluation meetings, they discover unexpected insights: The manufacturing demonstrations fascinate international visitors, while the historical presentations create pride among local citizens. Their final pavilion could incorporate rotating demonstrations of modern industry, displays of traditional craftsmanship, and a slideshow theater, resulting in an exhibition created through practical testing rather than abstract debate.

The Scientific Method and Stretch Collaboration

Kahane’s iterative approach resembles the scientific method, but with a crucial difference. Like scientific inquiry, stretch collaboration involves observing a situation, generating multiple possibilities, testing assumptions with experiments, and learning from feedback and failure. Yet while scientists assume there’s an objective truth to be discovered, Kahane suggests that in complex human systems, multiple truths can exist simultaneously. This becomes particularly important when we consider that even science itself isn’t as objective as we traditionally assume: Scientific investigation is inherently perspective-dependent, with observations and conclusions shaped by the observer’s frame of reference.

Just as Einstein showed that measurements like velocity depend on the observer’s position, collaborative solutions depend on participants’ perspectives. Kahane’s approach doesn’t try to eliminate these different viewpoints to reach a single “right” answer; it accepts them as equally valid realities. While the scientific method assumes everyone will converge on one right answer if they follow the proper steps, stretch collaboration maintains science’s experimental mindset while releasing the expectation of a single solution. By embracing both the rigorous testing of science and the pluralistic nature of human experience, collaborators can create a way forward that works for everyone.

Principle #3: Focus on Changing Your Own Contribution

The third principle of stretch collaboration focuses on what’s entirely within our control: our own participation in the situation. Rather than trying to change others—which is often futile and frustrating—stretch collaboration requires us to step into the game and change ourselves.

Conventional collaboration often devolves into finger-pointing and blame. We focus on what others are doing wrong and how they need to change: “If only the other department would communicate better,” or “If only our partners would fulfill their commitments.” This approach is fundamentally disempowering because it places responsibility for progress on factors outside our control. It also makes others defensive, which makes them less likely to change.

(Shortform note: Effective collaboration may require an additional step that’s absent from Kahane’s framework—processing disappointment before shifting our focus to what we can control. In Jonathan Safran Foer’s short story “The Sixth Borough,” New York residents face a situation beyond their control when a neighboring borough drifts away despite attempts to anchor it. Before they can act, they must mourn what they’re losing: Many didn’t want their city to change, just as we get attached to how we want things to be. Unable to save the entire borough, the New Yorkers pull Central Park from the Sixth Borough into Manhattan, suggesting that sometimes we don’t just have to alter our behavior, but also reimagine our goals.)

Stretch collaboration requires shifting our focus from changing others to changing our own contribution to the problematic situation. This doesn’t mean accepting all responsibility or ignoring others’ actions; it means recognizing that the only element we can directly control is our own behavior. When you change your participation, it creates ripple effects. Every social system (team, organization, or community) develops habitual patterns of interaction. When you change your part in these patterns, it creates openings for new dynamics. While you can’t directly control how others act, your behavior creates incentives and opportunities for them to respond differently. By changing yourself, you make it easier for others to change as well.

(Shortform note: To understand how one person can create ripple effects through an entire social system, imagine a mangrove tree. Mangroves don’t just passively exist in their coastal environment—they transform it. Their complex root systems filter water, trap sediments, and create entirely new habitats for countless species. What starts as a single tree’s adaptation can transform an entire coastline over time. Similarly, the Bronfenbrenner ecological model shows that your interactions directly affect your immediate environment, which then influences broader social contexts—and changes established patterns of interaction. When you change how you participate, you’re creating new conditions that change how others respond to you.)

Kahane identifies three specific ways we can change how we participate in collaborative situations:

First, you can change how you look at the situation by recognizing that your perspective is just one of many valid viewpoints. Do this by challenging your assumptions about others’ motivations and intentions. Look for your blind spots and how they affect your understanding. Consider how you might be contributing to the very problems you’re criticizing.

(Shortform note: Recognizing that your perspective is just one of many valid viewpoints is perhaps the most difficult shift required for stretch collaboration. In “The Incredible Buddha Boy,” George Saunders observes that our minds constantly ask what we would prefer rather than trying to understand what is. To Buddhists, transcendence means getting out of the habitual patterns we normally inhabit. This is what Kahane also asks us to do: Saunders describes how we possess multiple energies and perspectives within ourselves, and this multiplicity mirrors the diversity of perspectives we encounter in others. Collaboration requires not just acknowledging other viewpoints, but actively working against the mind’s tendency to center itself in every story.)

Second, you can transform how you talk and listen by moving beyond downloading (speaking from fixed positions) to more generative modes. Practice dialoguing: Speak authentically about your experience rather than abstractly about “the facts.” Develop the capacity for presencing: Listen for emerging possibilities rather than just confirming what you already believe. Incorporate more genuine questions and fewer definitive statements in your communication.

Third, you can modify your actions by experimenting with different behaviors and noticing their effects. Take risks by stepping outside your usual role or position. Make unilateral moves toward the outcome you want to see. Model the collaborative behavior you want others to adopt—not as a manipulation tactic, but as a genuine commitment to changing the dynamic.

Surrendering Control to Change Ourselves

While Kahane focuses on changing our actions, the film Groundhog Day reveals another dimension: the internal transformation that precedes behavioral change. In this 1993 comedy, weatherman Phil Connors (Bill Murray) becomes trapped in a supernatural time loop, forced to relive February 2nd over and over again. No matter what he does during the day—whether constructive or destructive—he wakes up each morning to the same radio song, the same people, and the same events. Initially, he responds with frustration, then hedonism (using his knowledge of the day’s events for personal gain), and eventually despair—feeling that nothing he does matters and nothing will ever change.

But after countless repeated days, Phil finally accepts his lack of control over his situation. This frees him to experiment with new ways of engaging with others: Instead of manipulating outcomes or people, he begins developing genuine skills (piano playing, ice sculpting) and performing acts of service throughout the town. Similarly, in difficult collaborations, surrendering to our lack of control might free us to participate in new ways. When we stop trying to change others or to manipulate outcomes, we can focus on what we can genuinely contribute. Like Phil, whose loop only breaks when he finds meaning in connection, we might learn that changing how we participate creates new possibilities for collaboration.

Practical Steps to Change Your Own Participation

Kahane outlines the steps you can take to change your own participation in a difficult situation:

1) Develop greater self-awareness. Notice your habitual responses in difficult situations and pay attention to your triggers and reactive patterns. Seek feedback about how others experience your participation, even when that feedback might be uncomfortable to hear. Create a regular practice of reflection on your contribution to collaborative outcomes.

2) With this awareness as your foundation, you can practice new behaviors. Identify specific actions you want to modify—perhaps interrupting less, asking more questions, or expressing disagreement more constructively. Start small with experiments in lower-stakes situations before attempting changes in your most challenging collaborations. Before key interactions, take time to visualize different ways you might respond to triggers or challenges. Afterward, debrief with yourself or a trusted colleague to reflect on what worked and what didn’t.

Cultivating Mindfulness for Self-Regulation

Mindfulness practice helps develop many of the self-regulation skills Kahane identifies. It enhances self-awareness by creating space between receiving information and reacting to it, which allows you to notice your habitual responses—like whether you interrupt others, become defensive, or withdraw—before acting on them. Mindfulness also helps you approach new behaviors with curiosity instead of judgment, and the self-reflection central to mindfulness enables the type of debriefing Kahane suggests. Mindfulness practitioners learn to nonjudgmentally acknowledge what worked and what didn’t, which makes learning from experiments more effective and less draining.

Similarly, mindfulness also supports effective feedback-seeking by helping you approach others’ perspectives with curiosity rather than defensiveness. This creates a sense of psychological safety that makes it easier to solicit honest input about how others experience your participation. Perhaps most importantly, mindfulness helps you cultivate self-compassion—treating yourself with the same kindness you would offer a friend when confronting your own missteps. Self-compassion reduces harsh self-criticism that might otherwise prevent you from acknowledging areas for growth, helping you cultivate exactly the mindset needed to change your contributions to challenging collaborative situations.

3) For sustainable change, build support systems around your practice. Find colleagues or friends who can serve as “mirrors,” offering honest feedback about your behavior. Create simple reminders—perhaps a note on your phone or computer—about the changes you’re trying to make. Establish regular reflection practices, such as weekly journal entries or conversations with a mentor. Throughout this process, celebrate small wins while showing compassion to yourself when you fall short; changing ingrained patterns takes time and persistence.

(Shortform note: Behavioral science research reveals why building support systems for your changes is so powerful: Environment often matters more than motivation in shaping our actions. When you place a note on your phone about the behaviors you’re trying to change, you create what behavioral economists call a “nudge” that guides your decisions without requiring constant willpower. Similarly, reflection practices like journaling or talking to a mentor make behavior change a natural part of your routine. Finding colleagues who provide honest feedback creates accountability that increases your follow-through on intentions, helping you to keep moving forward even when your motivation fluctuates.)

For example, imagine that during a spaceflight training sequence, tension develops between the flight director and a communications specialist over protocol procedures. The communications specialist notices that she becomes defensive whenever the director questions transmission schedules, often contradicting him before he finishes explaining his operational concerns. After requesting feedback from a senior colleague, the specialist might realize that she views the director as an adversary rather than a partner. The specialist could identify specific behaviors to change, such as contradicting others, dismissing their concerns, and using a clipped tone over the intercom.

By practicing her new behaviors during simulated countdowns, the specialist prepares for critical communications by visualizing herself responding with professional clarity instead of defensiveness. During the next full mission simulation, when the director raises concerns about transmission timing, the specialist instead acknowledges the issue and suggests an alternative procedure—leading to a more efficient communication protocol. The mission parameters haven’t changed, but by adjusting one person’s approach, a strained working relationship has transformed into an effective partnership.