I guess successful outsourcing depends upon “what” you’re actually outsourcing. Good writers are hard to find.

My first foray into outsourcing has been to actually hand over things I don’t like doing OUTSIDE of business: cleaning my house, grocery shopping, tracking people’s birthdays, etc. I was not born to be a house wife, clearly. But you’re right, Jason, it’s time to make the leap and move outsourcing to my business. Thanks for the article – and the reminder!

I suppose there are two problems to avoid: outsourcing too quickly OR outsourcing too late.

And I like your comment about taking it in steps. First, start with the basic tasks. Not only will this be easier to manage, you’ll also get lots of experience working with someone else before jumping into the deep end with consultant, sales reps, and the like.

Excellent points!

I would make one additional point, though, is that if you can’t afford to outsource because of cash flow issues, you either need to do the work yourself, or negotiate up front. I’ve been outsourced to by someone who couldn’t afford to pay – and it’s really irritating to do the work and not be compensated.

I think what I would therefore add to this would be a measure of having reached the stage where you need to either hire someone, or outsource some of your work. At that point, these questions and comments you make provide real value. I think it was Joel Spolsky who said that his first hire was for an admin assistant – in a technical company, because he didn’t want to do that work anymore, and it wasn’t core to his business.

When you reach the point that you can afford to hire someone, consider outsourcing some of your support tasks before hiring someone.

1. Be very detailed.
You’ve been doing this work for months or even years in some cases, so you can’t expect these people to know everything you do.

2. Create videos, manuals, or other materials.
Training materials are essential. This way, if you need to train someone else at another time or if the assistant forgets how to do something, you’re not losing more of your time.

3. Demand excellence.
You absolutely must insist that your assistants get their work done correctly. That’s what you’re paying them to do, so they should do it.

Stephanie’s right – training is so critical to successful outsourcing. I’m glad she pointed it out.