Collaborating with The Enemy

This book met me in a moment of deep frustration.

I was tired of conflict.

Tired of watching conversations collapse before they even began.

Tired of the tug-of-war that never seemed to lead to progress — just exhaustion.

Adam Kahane doesn’t come in with idealism. He doesn’t sugarcoat conflict. He doesn’t tell you to “just find common ground.” In fact, he starts from the honest truth: Sometimes, you won’t agree. Sometimes, you won’t like each other. Sometimes, you won’t trust each other. But you may still need to work together.

That’s where this book begins — and what unfolds is not a how-to, but a human-to-human guide for navigating the messy, maddening, but necessary terrain of real-world collaboration.

Here are 7 lessons that stopped me, softened me, and stayed with me:

1. Collaboration is a Choice — Not a Compromise

“You don’t have to collaborate. But sometimes you can’t move forward without it.” This hit me hard. So often, we see collaboration as something we’re forced into. But Kahane reframes it: it’s a choice — sometimes a painful one — to stay in the room with people we don’t agree with, because something bigger is at stake.

It’s not weakness. It’s strategic courage.

2. You Can’t Control the Whole 

In a world that often rewards control and domination, Kahane reminds us that real collaboration is letting go of the need to steer the whole ship. We each bring our piece. We each share the space. This kind of humility is vulnerable. It feels unsafe. But it’s also the seed of actual change.

3. Don’t Wait for Trust to Begin 

“Collaboration does not require agreement, liking, or trust — but it does require a willingness to keep showing up.” This one challenged everything I thought I knew.

Kahane says trust isn’t a prerequisite , it’s a product of collaboration. We build trust by being willing to stay in the discomfort, even when it’s tense, even when our defenses are up.

This gave me permission to start small. To not wait until it “felt right.” Just to begin.

4. Step Forward, Then Step Back

He introduces this dance: assertive humility. The idea that sometimes we need to speak up boldly — and sometimes we need to listen with open hands. Collaboration isn’t about shrinking. It’s about choosing when to lead, and when to let others lead. That balance is hard. And healing.

5. Conflict Is Not the Problem — Stuckness Is

We fear conflict. But Kahane reframes it: the absence of movement is what destroys progress — not disagreement. This was liberating. It allowed me to see conflict not as failure, but as friction that can actually power transformation — if we stay in it long enough.

6. Let Go of the Fantasy of Control

Kahane calls this “emergent collaboration.” That means we can’t script the outcome. We can only keep adjusting, listening, responding. For planners, fixers, and perfectionists (me), this is uncomfortable. But it’s also freeing. Because it allows space for something new — something better than what we could have imagined alone.

7. Sometimes, the Enemy Is Not Out There — It’s the Fear Within

This may not be a headline in the book, but it’s what I walked away with.

The “enemy” is sometimes a person.

But often, it’s a fear.

A need to be right. A wound we haven’t healed. A story we’re still clinging to.

Kahane doesn’t just teach us how to collaborate with others — he invites us to collaborate with ourselves. With our doubts. With our resistance. With our humanity.

Collaborating with the Enemy isn’t a feel-good book. It’s a feel-deep book.

It doesn’t ask you to pretend everything is fine. It asks you to stay at the table anyway. It teaches you to move through complexity not with perfection, but with presence.

Adam Kahane has worked in post-apartheid South Africa, in violent political divides, in broken systems where no one wanted to budge — and he’s learned that sometimes, the most powerful thing we can do is simply not walk away.