Andrew M. Hahn

A few years ago, after reading Ferriss’ The 4-Hour Workweek I was convinced outsourcing my work was the way to go. How could it not be? He pitches it as the end-all-be-all for achieving freedom from the daily grind.

“What could go wrong,” I reasoned. “Just follow Tim’s advice and be specific in your requests.”

Like any good salesman, Tim is selling an idea. He’s selling the idea of freedom. He’s selling to office drones who want out. But once you start outsourcing your life, there are equal parts “wow this is awesome” and “what have I done?” moments. While I haven’t figured out how to cut my life back to four hours (I doubt that will ever be a goal for me, truthfully), I’ve been able to shave off 15 of a potential 60 hour week—saving my sanity and the day at the same time.

For example, I hired a researcher that, for $20 an hour compiled a three-year editorial calendar and blog slugs for a client. Ten hours and two hundred dollars later, we had more blog material than we knew what do to with. And it was quality stuff.

Another time I hired a designer who plowed through a time-consuming project while I traveled. It worked out well: he worked while I slept and I gave him direction via email while he snoozed. Brilliant, right? There were some hiccups, but it came out alright in the end.

On the other hand, I once hired a guy and gave him very specific instructions on a project. I shared a Dropbox folder with him, assuming that he’d work directly off the files and I’d have immediate access to his changes for last-second tweaks. Instead, he downloaded them and worked off a local copy. When he uploaded the files…I spotted a typo. NOOO! Now I had less than an hour to deliver the project—it was safely tucked away on a his computer, a half a world away.

So it’s a mixed bag. Sometimes my off-shore developers will knock out a project in a third of the time for a tenth of the cost. Other times, they are so focused on solving the specific task I’ve set them to that they inadvertently break three other things—causing more revisions and added frustration.

If you’re thinking of outsourcing, here are a few things to keep in mind:

1. You get what you pay for. My experience$10/hr developers and $6/hr VAs has shown me that I get what I pay for. I’ve had much more success by seeking out those who charge a bit more.
2. Be clear. I’ve been on both ends of providing direction and feedback, and no matter what the skill level is for the person you’re managing, it’s always good to be as clear as possible. Kick off the project with a call—Skype preferably. When providing feedback, mark up a PDF or provide a screen shot rather than emailing a punch list.
3. Test the waters. Often times when I’m hiring someone for the first time, I’ll give them a small assignment to see how they do. If they do good work, I bring them on for a larger or more complicated project.
4. Be respectful. Recently a contractor apologized for the time it took to answer an email (it was maybe 30 minutes). “I was eating my dinner,” he said. Of course he as to eat, and sleep—not to mention live a life. It’s easy to fall into the idea that you’re hiring a tool. If you think that, you’re the tool. These are people trying to make a living, trying to carve out a life for themselves. Be nice. Be generous. Don’t be a jerk. Say thank you.
5. Temper negative feedback. When hiring through oDesk or Elance, there’s an opportunity to provide feedback. Just one piece of advice: be nicer than you should: This is a human who’s trying to make a living, not a product on Amazon.

It’s a new age of flexible, ad hoc teams. It’s cloud outsourcing. There’s new territory to explore and new pitfalls to avoid. And while I’ve had my fair share of mishaps, overall I believe in the new flexible team model.

I’d love to hear your experience in how outsourcing has changed the way you live and work.