We’ve outsourced lots of projects over the past few years. It has generally, but not always, gone well.

My favorite outsourcing story is what happened with Rosen.com. It’s a huge site, and we wanted to move it from a proprietary content management system to an open-source platform. We selected WordPress and went to work on finding someone to do the work.

We got several quotes from local web design shops. They went as high as $35,000 to do the work. We were given a timeline that involved six months worth of meetings, feedback, approvals, and the like.

We put the project up on Elance.com to see what we’d get back. We got a bunch of bids and on a lark took the $500 bid to see what might happen. We figured that if it didn’t work out, we’d only be out $500. The guy who offered the bid said he’d have it done in two weeks.

Two weeks later—voila!—the site was finished. We paid our $500 and moved on. Amazing.

We’ve since outsourced other design and programming work, writing, and a range of other things. We’ve learned a bunch of lessons, but one stands out above all the others.

The key to successful outsourcing is properly defining the project. It’s critical that you decide in advance what you want and clearly articulate your specifications. This is not a “I’ll know it when I see it” game. Before you start, you’ve got to know what it’s going to look like when it’s finished.

That holds true in the literal sense for software design and projects of that ilk. It’s less literal, but still important, with graphic design. If you have no idea what you want, you’re not likely to get what you want. Spend a bunch of time up front thinking through what you hope to achieve and how you’ll define success. The clearer you are, the more likely you are to end up with a result that works for you.

We’ve outsourced some legal work in the past. Legal work, for us anyway, is the best example to use to explain the need to define the project. For instance, you can’t simply tell someone to handle the appeal and expect it work out. You need to break out the parts, define your expectations, and assign each task. Who’s going to get the record prepared? Who’s going to call the clerk? The court reporter? Who’s going to talk to the client as the appeal progresses? Who’s going to draft the brief? Format it for printing? Print it? Upload it? Conduct oral argument? And on and on. You’ve got to clearly define the project if you’re going to achieve the results you want.

Outsourcing can be an amazing way to extend your capabilities. Just don’t go into it without carefully defining what you expect to get out of it.