Coaching practices for Steelman vs Sycophancy

Describe almost anything you are working through and IX Coach finds the practices whose real-world fit is closest. For Steelman vs Sycophancy, these are the strongest matches in the current practice library.

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

  • I go through the motions of considering the other side and then somehow always conclude I was right all along
  • There are a few ways to read the view I’m up against, and I keep reaching for the flimsiest one because it’s the easiest to knock down
  • I water down the other side’s argument with little "they claim, without proof" jabs because I’m scared that stating it fairly will look like I agree with it
  • I’ve settled on my position and I can feel how much I want it to be right, which is exactly why I don’t trust it yet
  • I keep winning this argument in my head against the dumbest version of what they think, and then it goes nowhere in real life

Practices that may help

  1. Distinguish steelmanning from sycophancy
    Charitably interpreting a position is not the same as agreeing with it, refusing to disagree, or softening your critique to avoid conflict.
    Steelmanning
  2. Find the strongest version of the opposing view
    If there are multiple ways to interpret a position, choose the most defensible one.
    Steelmanning
  3. Steelmanning
    Steelmanning — popularized by Daniel Dennett as a core intellectual virtue — means reconstructing an opposing position in its strongest, most charitable form before responding to it. It is the deliberate inverse of strawmanning. The practice is well-established in philosophy and structured debate; direct experimental evidence for its effects on reasoning quality is limited, but its mechanism is logically sound.
  4. Separate steelmanning from endorsing
    Accurately represent a view without implying you agree with it.
    Steelmanning
  5. Ask what alternative perspectives would say
    Deliberately steelman the strongest objection to your current position before treating it as settled.
    Socratic Questioning
  6. Steelman the opposing view before rebutting it
    Reconstruct the strongest possible version of the argument you disagree with — then respond to that.
    Naive Realism: Why Everyone Thinks They See Things as They Are
  7. Know your two selves (Adam I and Adam II)
    Distinguish the self that wants to build and achieve from the self that wants to be good.
    The Eulogy Virtues: Building a Life of Character
  8. Apply the double-standard check: would I accept this reasoning if it pointed the other way?
    Test whether you are holding your team’s arguments to a lower bar than the other side’s.
    The Scout Mindset
  9. Insist on objective criteria
    Anchor the deal to independent standards — market rates, precedent, expert opinion — not willpower.
    Getting to Yes: Principled Negotiation
  10. Use mutual dependence as a motivation to act well
    Remember that others depend on the same fabric you do — and act in ways that strengthen it.
    Sympatheia — the Stoic Practice of Universal Interconnection

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