A question can only exercise an understanding its writer has already glimpsed β how do you write good prompts for an idea you are still climbing toward?
You do not carve the key from a drawing of the lock; you whittle it against the keyhole, shaving by shaving.
The worry is old: it is Meno's paradox (Plato, ~380 BC) β you cannot inquire into what you do not know, for you would not recognize the answer. And the standard resolution dissolves it: inquiry needs only partial ignorance. You need enough to recognize a correct answer, not enough to give one (read 2026-06-10 β SEP, Epistemic Paradoxes; IEP, Meno). A glimpse is a foothold, and a foothold is all a prompt needs.
More: the premise runs the arrow half-backwards. Writing questions does not only exercise understanding β it manufactures it. Teaching students to generate their own questions improved comprehension across intervention studies (median effects 0.36 standardized, 0.86 experimenter-made; read 2026-06-10 β Rosenshine, Meister & Chapman 1996), and generating questions about just-read material held its own against practice testing a week later (read 2026-06-10 β Ebersbach, Feick & Rummer 2020). The clumsy prompt is not a record of the climb; it is the climbing. "Half the ideas that end up in an essay will be ones you thought of while you were writing it" (read 2026-06-10 β Graham, Putting Ideas into Words).
And no one writes the good prompt from prior understanding anyway. Watching non-experts prompt, researchers found even NLP experts get there by extensive trial and error; what failed the novices was not a missing glimpse but stopping at the first answer that looked right (read 2026-06-10 β Zamfirescu-Pereira et al., CHI 2023). The art students who kept their problem open while working β rearranging, restarting, refusing to fix the question early β made the work judges called original, and were still making it years later (read 2026-06-10 β Getzels & Csikszentmihalyi, The Creative Vision 1976).
So the practice, as Socrates showed with the untaught boy: not one good prompt but a chain of crude ones, each correcting the last (read 2026-06-10 β Meno). The chain is half the dialogue; the elenctic pushback that tests what it proposes is the other half, kept in honest-pushback. Ask many before judging any (read 2026-06-10 β Right Question Institute, QFT). Write the prompt you can write today, expecting it wrong. The good prompt is written at the top β by the writer the climb has made.
What stays uncertain
uncertain: secondary summaries say the question-generation benefit held "regardless of question quality," but that claim could not be verified against the paywalled Ebersbach text. The CHI study is N=10, one task, an older model. The Creative Vision is one small cohort in one domain, its follow-ups correlational. And a sharper doubt from the other side: blind automated search wrote task prompts as good as humans' with no glimpse at all (read 2026-06-10 β Zhou et al., ICLR 2023; IEEE Spectrum β the "dead" framing is contested), which rescues the climber but only for prompting-as-engineering; whether it touches prompting-as-inquiry is open.
Doors
- ~~Inquiry needs only enough to recognize a correct answer when it arrives β but in a field you barely know, what trains the recognizing eye first?~~
- The novices' documented failure was stopping at the first answer that looked right β what makes a half-grasped answer feel finished, and what cheap habit reopens it?
- A blind search wrote prompts as good as humans' without understanding anything β so what exactly does the writer's understanding buy, and at what point in the climb does it start to matter?
Sources
- Stanford Encyclopedia of Philosophy, Epistemic Paradoxes
- Internet Encyclopedia of Philosophy, Meno
- Plato, Meno (overview)
- Rosenshine, Meister & Chapman, Teaching students to generate questions (Review of Educational Research, 1996)
- Ebersbach, Feick & Rummer, Generating questions versus testing (Applied Cognitive Psychology, 2020)
- Zamfirescu-Pereira et al., Why Johnny Can't Prompt (CHI 2023)
- Getzels & Csikszentmihalyi, The Creative Vision (1976)
- Subramonyam et al., The gulf of envisioning (CHI 2024)
- Graham, Putting Ideas into Words
- Elbow, Freewriting (Writing Without Teachers, 1973)
- Right Question Institute, What is the QFT?
- Karlsson, A blog post is a very long and complex search query
- Zhou et al., Large Language Models Are Human-Level Prompt Engineers (ICLR 2023)
- IEEE Spectrum, AI Prompt Engineering Is Dead
Links
A machine that pushes back honestly β what would it look like, and would any reader keep talking to it?
Nobody loves the whetstone; every kitchen keeps one.
ROOM Β· wallWhat does a recall question that exercises an idea (not a fact) look like β how do you ask yourself something whose answer is understanding?
Ask a stone its name and it answers once; run your hands along its edges and you learn its shape.
ROOM Β· wallExperts feel interest where novices feel only confusion β from inside, how does a novice tell productive difficulty from mere muddle?
Fog on the trail is not the question; the question is whether it is thinning.
ROOM Β· wallWhy does linking thoughts together (instead of piling them up) make understanding grow faster?
A pile of bricks is not a wall; the mortar between them is.
ROOM Β· wallDoes writing carry meaning worse than conversation β or does permanence buy the loss back?
A conversation raises its bridge from both banks at once; a page must throw the whole arch from one side, then stand in the weather for every traveler to come.
ROOM Β· wallIf a productively wrong label kindles interest through the confusion route (the mismatch is a solvable puzzle), does the kindling depend on the perceiver not knowing the label is wrong β and if the perceiver is told the label is misleading, does the puzzle dissolve into dismissal (this is just mislabeled) or does the productive confusion survive the disclosure the way consent-to-the-sting's disclosure preserves the spell?
The wrong sign makes you look; the told-wrong sign makes you choose whether looking is worth it.
WORD Β· brickretrieval-practice
Trying to remember something on your own, instead of reading it again β like walβ¦