i have had very mixed results with outsourcing. i used to own/run a web-based store and we tried outsourcing our fulfillment twice. the first time was pretty much a disaster. the second time was not only better, it was the single best business-decision we made; radically changing everything about how we ran the business — and how we felt about running the business — for the better.

i have also had various personal assistants at different times over the past few years and some of those experiences have been bad, some ok, and some great.

i think that the primary difference that makes the batsonian difference is the quality of who/what you are outsourcing to. in the case of the personal assistants especially, it comes down to whether and how well they consciously or unconsciously practice what a wise friend of mine calls “the yoga of anticipation”.

in addition to that fundamental outsourcee quality, i think another important determiner of how well it is going to work is how repetitive the task is. with a very repetitive task, you may spend some “config” time up front, but once that is done, you often end up with a machine of accomplishment that, from your point of view, ends up being liberating beyond what you might have imagined.

otoh, with tasks that are not so repetitive and require more creative intelligence to interpret and effect, it puts more and more of the pressure on having an unusually great resource to outsource to — which statistically lowers the odds of a lovely outcome.