I've been thinking for a while about what makes for a good question. What first got me started thinking was Will Nediger's excellent Scattergories 2 set. I thought it was one of the most interesting and fun sets I've played, but I wasn't really sure why that was, other than the obvious fact that I found the questions to be excellent. Having thought a bit, I've got some ideas about writing questions that are memorable, as opposed to just playable.
I think it starts with "high-value clues." I take as a given that all clues are factually correct, grammatically coherent, and uniquely identifying. But within those parameters, it's still possible to produce a "low-value clue." Take, for instance, the clue "This song has been covered by Richie Havens, Todd Rundgren, Peter Gabriel, and Ben Harper." It's certainly factually correct; all of those artists have covered "Strawberry Fields Forever." It's grammatically coherent. It's probably (although I haven't verified this for certain) uniquely identifying, simply because it's doubtful that each one of that motley assortment of artists has covered any other single song. But it's also a completely joyless procession of names, devoid of any context and difficult only for that reason, that reveals nothing interesting about the answer. After hearing a round of questions packed dense with dull clues of this sort, you can't help but imagine the writer chained to the desk, producing tossup after tossup out of rote, duty-bound necessity.
A high-value clue, by contrast, tells the player something interesting about the answer. It speaks to something that would interest someone who is interested in the question's subject. It pulls clues from materials that people who are interested in the subject would encounter in their quest to become more knowledgeable on the topic. It includes helpful contextual information that might lead the players toward the answer. It might even make a connection between its subject and other material that quizbowlers are likely to find interesting. (One of the joys of writing for a quizbowl audience is that there are few other groups you can be sure will appreciate the fact of an unlikely connection between two seemingly unrelated and academically interesting subjects.) In short, a high-value clue makes it clear that the writer is interested in the subject, and, rather than producing questions out of dreary obligation, actually has things she wants to say.
One of the best ways to guide each clue toward the high-value ideal is to start your question with a theme in mind. Perhaps you have decided to write a geography tossup on the sights of London. Instead of simply picking four or five of the millions of possible clues, which can easily lead down the gray, low-value path, perhaps you'll decide to focus on the city's museums, monuments, or public squares. Imposing such a restriction on yourself immediately forces you to start looking for interesting themes and connections, and once you've got those in mind, writing a question that engages the player is not difficult. I've found that a particularly good way to pick a theme is to take an interesting tidbit--I often take mental note of bizarre confluences between popular and "high" culture, for instance--and think about how that could be the basis for a question. The fact that you now have something to say--even if that something is "Salafism was partly inspired by a problematic Christmas song"--will immediately get you thinking about high-value ideas like source material, context, and what might be interesting to people interested in the subject.
Finally, I'd encourage people never to forget the bonuses when it comes to writing interesting questions full of high-value clues. Too often, the hard or easy part of a bonus seems to be based on some almost random, tenuously connected piece of information chosen only because it fits the difficulty structure. This is a shame, because a bonus is a great structure for a thematic idea that doesn't quite work for a tossup, or even for one that does--most writers would be better served by turning some of their great tossup ideas into well-considered bonuses instead of treating them, as is often the case, as a lesser form of question. Starting with a theme in mind can often lead to bonuses that test on enlightening connections between seemingly unrelated subject matters, and gives players the rewarding experience of understanding the connection between each of the answers you choose.
Elaborate on the merits of specific tournaments or have general theoretical discussion here.
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