Coaching practices for I Tried to Walk Someone Newer Through How I'd Handle This and Kept Hitting Questions I Couldn't Answer Cleanly and it Dawned on Me That the Spots Where I Go Vague Explaining it Are Exactly the Spots Where My Own Grasp is Thinner Than I'd Assumed

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

  • When I’m explaining something and hit a spot where I get vague or hand-wave past it, my instinct is to tell myself it’s just a wording problem and keep going
  • I tried to walk someone newer through how I’d handle this and kept hitting questions I couldn’t answer cleanly
  • When I try to explain this to someone who knows nothing about it and they keep asking "but why does that happen?" at exactly the spots I’d normally skate over, I get stuck and exposed
  • I keep trying to imagine how this lands for a total beginner, but I can’t actually un-know what I know
  • I have this vague nagging sense that I should "study the whole thing more," but it’s so unfocused I never actually do it

Practices that may help

  1. Pinpoint where the explanation breaks
    Treat every stumble, hand-wave, or jargon-grab as a flag for a real gap.
    The Feynman Technique, Step by Step
  2. Teach cases to solidify and test your own patterns
    Explaining your recognition logic to others forces the implicit to become explicit and exposes gaps.
    Recognition-Primed Decision Making
  3. Third-party explanation test
    Explain the concept to a person who knows nothing about it and let their questions expose your gaps.
    Illusion of Explanatory Depth: You Know Less Than You Think
  4. Find a genuine novice to test your explanation on
    Before the real audience, explain to someone who actually doesn’t know.
    The Curse of Knowledge: Why Experts Struggle to Teach
  5. Knowledge-boundary identification
    Map the exact point where your understanding runs out rather than treating it as a vague area of weakness.
    Illusion of Explanatory Depth: You Know Less Than You Think
  6. Push the "why" until you hit what you don’t know
    Keep asking why of your own answer until you reach a gap, then go fill it.
    Elaborative Interrogation: Ask "Why Is This True?"
  7. Teach it to a real person
    Explain the concept to an actual listener who can ask questions back.
    The Feynman Technique, Step by Step
  8. Ask what the audience already knows before explaining
    Probe prior knowledge explicitly rather than assuming it.
    The Curse of Knowledge: Why Experts Struggle to Teach
  9. Write the explanation, do not just think it
    Put the "why" in writing so vague mental hand-waving cannot pass as understanding.
    Elaborative Interrogation: Ask "Why Is This True?"
  10. Apply the explanation test to gauge real understanding
    If you can’t explain something simply without notes, you probably don’t understand it as well as you think.
    The Dunning-Kruger Effect, Understood Clearly

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