Q: I have read a lot of books in my time and find the stories that are entered in contests are not that interesting. Doesn't the winner depend on what the judge likes? Also, how do I know if I am good, or how I can do better, if I can't let an authority read it? Thank you, Roxanne
A: Writing contests definitely have personalities, and the quality of the winners often depends upon the type of contest. Is it a large-scale national contest that attracts thousands of entries? Or is it a modest regional contest that may attract only a few dozen entries? The size of the entry pool matters a lot to the quality of the winner, as does the prestige of winning the contest. Just as you would match up your work to the right market—when attempting to publish a piece—you should match up your work with the right contest for your genre and experience.
You're right that contest judges do matter. Their bios/backgrounds often give you an idea of the level or tone of the contest. If you've read or enjoyed the work of a particular judge (assuming he or she is a published author), and you think your work shares the same sensibility, then all the better. (That's not to say that judges don't make surprising choices or go against the grain in their selections.)
I had the opportunity to manage several different types of contests run by Writer's Digest. We often used first-round judges who sifted through thousands of entries in an effort to pull out the cream of the crop (e.g., the top one or two percent). Then a big-name judge would make final selections. In some cases, a group of editors would decide the grand-prize winner, and rarely did everyone in the room agree. I've often seen the best piece (in my opinion) lose out to a more crowd-pleasing piece. It can be quite subjective.
Recently, there has been some controversy surrounding writing contests. Some writers feel they unscrupulously profit from entry fees and/or use biased judges. One site, www.Foetry.com, has attempted to raise a red flag on some contests, though their efforts have been highly criticized and controversial as well. But I think it is a needed wake-up call.
As far as knowing if you're any good, you might never know for sure. And nobody can tell you—even if they could, would it really matter? Wouldn't you still have the same question the next day (or with the next piece)? One thing's for sure: You'll write crap for a long time before you write something good. Even published writers struggle to write something good; everyone has shitty first drafts, as Anne Lamott says. You might want to read a book like Bird by Bird by Lamott to help you understand and work through this problem—because it's not going away any time soon.
However, I don't advise you to write in a vacuum; eventually you will need outside readers to tell you what's working and what's not. But an authority is hardly required; all you need is one, insightful reader who will give you an honest opinion.