
Should you Collaborate with the Enemy? | Adam Kahane
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If you're not part of the problem, you can't be part of the solution.
In this episode of Messy, Daniel Atlin sits down with global facilitator and systems practitioner Adam Kahane to explore what it really means to collaborate when agreement feels impossible.
They explore collaboration across deep divides, the courage to see our own part in the problem, and how change often starts in the smallest crack in a hardened system.
Drawing from his newly revised second edition of "Collaborating with the Enemy", Adam challenges the romantic idea that collaboration is always the right answer. Instead, he offers a more grounded framework: collaboration is one option among four, alongside forcing, adapting, and exiting. The key question is “When, and under what conditions, is collaboration the most viable path?”
The conversation explores several core ideas:
• "Enemy-fying": Adam’s invented word for the habit of labeling others as enemies simply because we disagree with them. In polarized systems, this reflex deepens fragmentation and limits our options.
• The Three Stretches of Collaboration:
1. Embrace conflict as well as connection
2. Experiment your way forward
3. Recognise your role in the game
• Power, Love, and Justice: Drawing on Martin Luther King Jr. and Paul Tillich, Adam frames social change as a tension between the drive to realize oneself (power), the drive to unify the separated (love), and the structures that balance the two (justice).
• Failure as Teacher: Adam speaks candidly about mistakes in both professional and personal contexts, arguing that experimentation, not certainty, is the only way forward in complex systems.
One of the key take aways for those interested in “Messy” leadership is that collaboration begins not with technique, but with introspection: Who am I in this system? How am I contributing to the very dynamics I’m frustrated by?
If you like this episode, share it with a friend. And buy Adam's book!
In this episode of Messy, Daniel Atlin sits down with global facilitator and systems practitioner Adam Kahane to explore what it really means to collaborate when agreement feels impossible.
They explore collaboration across deep divides, the courage to see our own part in the problem, and how change often starts in the smallest crack in a hardened system.
Drawing from his newly revised second edition of "Collaborating with the Enemy", Adam challenges the romantic idea that collaboration is always the right answer. Instead, he offers a more grounded framework: collaboration is one option among four, alongside forcing, adapting, and exiting. The key question is “When, and under what conditions, is collaboration the most viable path?”
The conversation explores several core ideas:
• "Enemy-fying": Adam’s invented word for the habit of labeling others as enemies simply because we disagree with them. In polarized systems, this reflex deepens fragmentation and limits our options.
• The Three Stretches of Collaboration:
1. Embrace conflict as well as connection
2. Experiment your way forward
3. Recognise your role in the game
• Power, Love, and Justice: Drawing on Martin Luther King Jr. and Paul Tillich, Adam frames social change as a tension between the drive to realize oneself (power), the drive to unify the separated (love), and the structures that balance the two (justice).
• Failure as Teacher: Adam speaks candidly about mistakes in both professional and personal contexts, arguing that experimentation, not certainty, is the only way forward in complex systems.
One of the key take aways for those interested in “Messy” leadership is that collaboration begins not with technique, but with introspection: Who am I in this system? How am I contributing to the very dynamics I’m frustrated by?
If you like this episode, share it with a friend. And buy Adam's book!
Chapters
- 00:00 Introduction and background
- 05:27 Montreal's influence: growing up across divides
- 08:48 The success and relevance of 'Collaborating with the Enemy'
- 10:10 Four options beyond collaboration
- 12:52 Enemy-fying: beyond black and white thinking
- 20:34 Love, power, and justice: the Tillich Framework
- 30:50 Embracing conflict and the Gottman Insight
- 42:02 Experimenting forward: crossing the river feeling for stones
- 45:14 Recognising your role in the game
- 48:56 Scenarios and future planning challenges





