Outsourced Wednesdays: Help us sublet our apartment
Outsourcing February 20th, 2008One major factor in making our 2-month trip to Mexico feasible was renting out our apartment while we were gone. Needless to say it went better than we anticipated. Below is the exchange I had with our assistant.
George,
Please take the attached description and photos and create a simple Backpack page with nice formatting. Then create a summarized version of the description and two of the photos (whichever two you think look best) and create a post on Craigslist. Have responses sent to your email address, filter out the most likely candidates, and post them here on my dashboard
Thanks,
-Jed
===========
He then created this page including the nice little image gallery, posted to Craigslist, and sent me a quick confirmation note. For some reason I suddenly worried that we priced it too high. Without first checking the dashboard, I fired off this note:
===========
George,
Sorry to bother, but can you edit the Craigslist listing to be $800
rather than $1000?Thanks,
-Jed
===========
Jed,
Have you looked at the dashboard yet? You’d be crazy. Maybe I’ll think of raising the price to $1200.
-George
### end task
As it turns out, over a dozen people responded that same afternoon, several of which had ideal circumstances and he had posted them to my “dashboard” (a Backpack page that he and I share). Within a few days we made the final arrangements with our temporary tenant, and saved a few thousand bucks during our trip!
Having an assistant with enough initiative to tell me I’m crazy and suggest a better solution can sometimes be quite helpful. 
Popularity: 11% [?]
Jed, this reminds me of a common issue with outsourcing:
Either an assistant doesn’t ask enough questions (and completes the task without asking you “Does this make sense, can we do it this way?”) or they ask too many questions and don’t get the task completed (and you’re left asking yourself, “Why didn’t they just do what I said?”)
There is a fine balance between having an assistant with the ability to follow rules to the “T” but also with the initiative and aptitude to think outside of the box and know when to question their “boss”.
@Rob-
And what I really like about our assistant is that he knows when to make suggestions and second-guess me a bit, but he doesn’t just take action without first running it past me (unless I’ve specifically told him “do what you think is best”).
That principle is something we’re planning on carrying into HTD: assistants that make suggestions and lower the mental effort of deciding on next steps, but don’t cross the line into “so I went ahead and did it.”