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I know I try to accomodate when someone asks me specifically to enter a contest through a PM.
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I disagree with this. I think all the designers here get enough of these that to me they tend to look like a cheap ploy to garner attention unless it's obviously personalized. I.e. "I really liked your second entry in the such-and-such contest". That shows that you're interested in me as a designer and you feel my style is appropriate to your company. Otherwise it looks like a form letter begging for attention.
I agree with Blackspot: feedback, feedback, feedback. There's nothing worse then seeing entries get completely ignored by the client and that's a sure way to get some people to not enter more designs. If you don't like an entry, I prefer a simple "no thank you" instead of silence. Be specific whenever possible.
I'd add the following:
Consistant feedback - Show interest in your contest and the designers will too. If you go a week without commenting the designers will work on more pressing issues and your design will get pushed to the back burner. Try to check in every couple of days at least.