First off, check the submission guidelines. I know this sounds obvious, but you have no idea how often people submit stories incorrectly. This means looking at more than just the deadline, word count and method of submission. Look at the types of stories they want. If they’re looking for an inspirational story and yours doesn’t mention God or faith, it might not be a good fit.

Assuming you have a story or two that appears to fit their guidelines, look at (read if possible) stories that have won in previous years. This will give you an even better idea of whether this is something your story might win. Your story should be similar in tone, theme, and/or style, but it still needs to be distinctly different from stories that have won in previous years. However, if they tend to choose melancholy tales and your story is a light-hearted romp, then this might not be the best contest for you.

Look at who has been winning this contest over the past few years. Do the winners tend to be established, mid-list, or newbies, or does it flucuate? If a contest tends to only pick established authors and you've yet to get a story published, you might want to spend your money elsewhere. This doesn't mean you can't win (as long as you fit their contest requirements), it just means your chances aren't as good and your time and money might be better spent elsewhere. Conversely, if you've been publishing regularly for 10 years, it's time to stop submitting to the contests geared toward newbies and start aiming a bit higher.

Consider why you’re entering this contest. Do you want money, exposure, publication or feedback? All contests offer some combination of these, and you need to decide what is important to you. Some authors use contests as a way to get constructive feedback on their stories from people in the industry. Others just want exposure, some want more money than they can get via normal publishing routes, and everyone wants to get published somehow. Identify your goal in submitting to a contest or award and then chose appropriately. (Oh, and I almost forgot praise and accolades are another reason to submit to certain awards.)

Let’s say you found a contest that fits perfectly with your goals, but none of your current stories quite match the requirements. Do you rewrite it? This is one of those case-by-case questions. Consider how much time you have to do the revisions well, and whether changes can be made without being obviously false additions. If you don’t have the time or ability to do it well, it’s not worth doing.

Something that comes up with contests and anthologies is whether or not to write a new story for a specific call for submissions. For example, last week I posted a call for stories about magically linked swords. Now, not many writers, even of fantasy, have stories like that lying around. So the question becomes, do you write a story strictly for this or not?

One fantasy author said their policy on whether to write to a specified theme or character for a contest or anthology was to do it only if a story presented itself. I kind of like that advice and I wish I could remember who said it. Returning to the sword example, if after reading the description you immediately (or a day or two later) got an idea that gripped your imagination, then sure, go for it. But if after a week or two nothing is coming to you, it’s better not to force it.

After these preliminary considerations, mainly the other things you can do to try and win a contest are to write cleanly, and write well. Get rid of all the typos and grammar mistakes, the flowery descriptions and florid expositions. Revise and edit with a clear head. Send it in and hope for the best.

As someone who hasn’t entered many contests, I’m sure I’ve missed a few things. Any other tips or warnings?