Coaching practices for How to Argue Both Sides

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Does this sound like the set of challenges you might be facing?

  • I catch myself arguing against the weakest, dumbest version of what they said
  • I keep losing the same argument by pushing harder, and it’s starting to dawn on me that I’ve never once tried to actually see it from their side first
  • We keep fighting on ten fronts at once and it’s exhausting and goes nowhere
  • I notice I’m really arguing against this person
  • The moment the other person starts talking I’m already loading my rebuttal

Practices that may help

  1. Steel-man before you rebut
    Restate the opposing view in its strongest form before you argue against it.
    Productive Disagreement, Made Practical
  2. See things from the other person’s point of view
    Try honestly to see things from the other person’s angle before you argue your own.
    How to Win Friends and Influence People, Made Practical
  3. Find the crux: the one claim that, if changed, would change the conclusion
    Locate the single empirical or value disagreement driving the whole dispute.
    Productive Disagreement, Made Practical
  4. Separate the argument from the arguer
    Address the claim on its merits, not the person’s motives or character.
    Productive Disagreement, Made Practical
  5. Practice "Tell me more" — defer rebuttal until genuine understanding
    Respond to an opposing view with curiosity before you respond with counter-argument.
    The Third Alternative, Made Practical
  6. Find mutual purpose
    Establish a shared goal both people care about so the conversation is "us vs the problem".
    Crucial Conversations, Made Practical
  7. Hold conflicting perspectives without collapsing
    When two people you respect disagree, hold both views as data instead of needing one to be simply right.
    Self-Authorship: Moving From the Socialized to the Self-Authored Mind
  8. Add the strongest objection to every major supporting reason
    For each supporting reason, find the best counter and put it on the map.
    Argument Mapping
  9. Roll with resistance instead of fighting it
    When you meet a push-back, soften and reflect rather than argue.
    Motivational Interviewing, Made Practical
  10. Consider the opposite
    Actively argue the case against your first conclusion before accepting it.
    Thinking, Fast and Slow, Made Usable

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