Ask for examples of previous work and for work referrals. Do basic due diligence here, as you would anywhere else.
Define your job clearly. State the number of articles you need, topic, deadlines, word count etc. The more detailed you can be, the better.
Don't be cheap. $5 for 500 words will buy you a worthless collection of words. Quality costs money.
Look for someone with experience in your industry (more on that below).
Define payment terms up front. It is a good idea to print out a contract that you and the outsourcer will sign, in order to protect yourself and to avoid conflict.
Start out with a simple project first if you've never dealt with a particular person/agency in order to try them out. As they deliver and you become more confident, you can start giving them more complex projects. This is how you build the relationship.
Keep in mind that in order to write for you, writers have to research the topic and come up with their own ideas. If they are new to the industry, expect articles with recycled content and no original ideas. I am not trying to trash writers, or say they don't know what they are writing about, but rather make the point that you should not expect expert level content with original ideas that will get you links when you hire someone on the outside with no experience in your industry. Before writing about a topic, writers sometimes spend only few hours (or less) reading the web, and then spit back what they learned in their own words. It cannot be original.
On the other hand, unless you're blogging for links, content does not have to be original. Sometimes all you need is food for the Google bot with targeted keywords, where OK content does just fine. It all depends on your goals.
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