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I feel intuitively, that a question should be answerable in the original form in which it was posted. That it should be hard, but not too hard, and that once you have found the solution, it is immediately obvious that it's the right solution.

However, Unfortunately, it is challenging to make a question which is exactly in the right difficulty/hint range. If you make the question too easy, it gets answered immediately, and if you make the question too hard, no one figures it out before it disappears from the hot list. What tends to happen, at least what I see, is that we choose to make questions too hard rather than too easy. The reasoning is simple, you can always add hints to a question to make it easier, but you can never take information away to make it more difficult.

Herein lies the problem, or at least it is a problem IMO. We have a lot of questions that can not be answered in their original form. You have to look through the original question, the hints, and the question-askers comments which might even appear inside of answers. So we are left with questions that are sometimes incomplete (all the info is not in the question), no one knows how difficult they are (it may have changed from way too hard to way too easy with a single hint), and which your ability to answer the question is highly dependent on when you visit it.

My question then is what (if anything) the community should do to address these problems. Is expecting a question to be answerable from the outset a naive extrapolation from books with a single-reader and inactive author? Should we establish rules or guidelines regarding how to deal with a floundering question? E.g. answer questions for clarity not but questions which narrow down the question (The way a professor might answer questions during a test).

Should there be suggested intervals for providing additional hints? E.g. if no progress is made for 4 hours, then you should add a hint.

At what point is it clear that there is too much involvement from the question-asker? Could I for instance do a "What am I?" 20 questions style. Where I post nothing from the start and only provide information when asked for it. (Sometimes questions feel like this with how much the question-asker needs to get involved).

And finally, what kind of feedback can we provide askers to encourage them to make their future questions into to the more desirable type of puzzles?

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    $\begingroup$ I personally think that, as a rule of thumb, OPs should aim at leaving "the perfect puzzle behind" even if - or especially if - it has been answered already in an ackward iterative communicative way. As you say, it is often hard to be get it right "the first time", but that should serve as no excuse: Posts on PuzzlingSE should not be for the moment, but - as all of SE - lasting. I think we should repeately communicate that to the puzzle posters. $\endgroup$
    – BmyGuest
    Commented Jun 21, 2016 at 22:33

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I think this whole question stems from the mistaken assumption that a good puzzle is a puzzle that takes a while to solve:

If you make the question too easy, it gets answered immediately, and if you make the question too hard, no one figures it out before it disappears from the hot list. What tends to happen, at least what I see, is that we choose to make questions too hard rather than too easy.

Just because a puzzle is answered quickly does not make it a poor puzzle. We should resist the temptation to make a puzzle too hard (i.e. virtually unsolvable) so that it takes time for someone to post a solution.

A puzzle that contains insufficient information is not a good puzzle. I would venture to say that (with a few notable exceptions), any puzzle on this site that is not solved within 24 hours is probably not a great puzzle. Most of the time, the reason puzzles aren't solved quickly isn't because they are "great" puzzles, that leave people feverishly working on a solution, but rather because they require so great a leap of intuition that it's unlikely that anyone will make it. (Some notable exceptions to this rule are puzzles that contain many parts. Each part is reasonably solvable, but it takes more time to put all the parts together and come up with a solution.)

Of my most-up-voted questions (that have solutions), the top five have the following times [h:m] from posting to solution:

  • 0:58
  • 1:45
  • 12:59 (this was posted in the evening in North America, so probably wasn't seen by many denizens of the site until the next morning)
  • 2:04
  • 0:16

Based on the votes and comments my questions have received, I would venture to say that they are "good" questions -- the community seems to enjoy solving them and appreciates them. I think that is partly because they didn't require huge leaps of intuition in order to come up with a solution. They still required some work and some thought, but there was enough information there to solve them, and to unambiguously recognize the solution when it was found.

The speed with which puzzles on this site are solved is largely due to "The many-eyes effect" (a term coined by xnor). If your puzzle is solved quickly, it should not be a mark of shame. Judge your puzzle on its reception, not on the speed with which it was solved.

Note also that in all the responses to "What are the features of a well-written puzzle?", nowhere does anyone state that a feature of a well-written puzzle is the amount of time it takes to solve it.

TL;DR

The short answer to your question is, "Ideally, not at all". A question should be posted in its entirety in a solvable form. If it is a good puzzle, it will be well-received and enjoyed, regardless of how long it takes to be solved. Hints should be unnecessary.

The puzzle-asker should ideally not have to edit the question at all. (There are, of course, times when we realize that a mistake was made in the question, or a crucial piece of information was left out, etc.,. In that case an edit is, of course, justified.)

Of course, we are not all expert puzzle-makers, and it's sometimes hard to judge how difficult a puzzle will be to solve. If we unintentionally make the puzzle too difficult, then we should edit the question to make it better. As a general rule (there are a few exceptions), adding hints is the lazy way of improving a poor question.

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    $\begingroup$ "If we unintentionally make the puzzle too difficult...edit the question...adding hints is the lazy way of improving a poor question". I think that's not true in every case. A puzzle that one person finds too difficult is at the right level for someone else. Adding hints has the advantage (compared to editing the question) that someone can choose to not read them. Thanks for your "times from posting to solution": so 1:34 doesn't imply "too easy", then... $\endgroup$
    – Rosie F
    Commented Jul 3, 2016 at 6:22

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