1. I establish a benchmark, usually me or whoever is doing the design. It would take me, say, a week to tweak a logo? If I can hire someone to do it in same time, at the same price, at higher quality, that's a win. You get what you pay for, so you want to set a decent budget.
2. I can put up a post requesting help with something, and a budget. Define clearly what I want. Usually, there's 20 or so applicants, half of whom are great.
3. Anyone who's hiring someone else to draw, filter them first. They're usually really low quality, fail to meet deadlines, and cheap.
4. Ask for a portfolio of work. It doesn't have to be great, but match my styles. Be tolerant of mistakes. If the person has several different work that looks exactly the same, filter them out too. Watch for plagiarism too - if you hire someone to draw you a logo of a pizza shop and the results are very similar to a Google search for "pizza logo", don't hire.
5. Filter it down some more. Don't hire someone who can't understand what the goal is; a good test is to have them repeat what you said in their own words. Don't hire anyone obviously lazy. Some have a pre-written questionnaire for clients - this is good.
6. You'll probably have a few choices remaining. This is a good place to negotiate, or just take what you have if it's down to one person. Don't haggle hard; you don't want them to be demotivated. In some situations (e.g. web designers), you might even want to propose more than what they offered, based on your budget.