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I’ve written before on the big mindset shift that I believe needs to happen before anyone can truly begin outsourcing effectively.


Even after undergoing that mindset shift, some people still have trouble figuring out exactly what tasks they can outsource or have a bad experience and give up on the whole thing. Here are my quick and dirty rules for outsourcing that can help you jump right in successfully:


Structured v. Unstructured

There are two kinds of things you can outsource: structured and unstructured tasks.


Structured tasks are the kinds of things you do regularly, or where the parameters of the task are defined enough it can easily be explained to someone else.


If something happens more than three times, or it’s defined but will take you more than an hour to complete, someone else should be doing it. To spark your inspiration, here’s a handful of basic tasks that someone else could be doing for you:


  • I have an insurance issue with a contractor.
    • VA is looking up and getting written quotes for a bunch of items.
  • At doctor they say you need to go to a specialist…
    • VA Schedules a time with XYZ Dr for my kids and add it to my Google calendar.
  • Send me gift ideas and figure that out (for parents / friends / etc.)
  • Cleanup photos and post them on FB / my blog etc.
  • Send thank you email (or handwritten cards) to people.
  • Thank a company for good service by an employee.
  • Complain to cable co and see if you can get fees lowered.
  • Setup an appointment to have my hot water heater looked at.
  • Get me 4 quotes to have my grass fertilized.
  • Call XYZ restaurant at 10a on Jan 20 and get me a reservation for X number of people for a Feb 20 at 7p (for more challenging places).


To keep it in line with the mindset shift, know that there will probably be some mistakes, but that what you gain in unclogging your mental to-do list is well worth the tradeoff. There’s no reason for you to be spending time on mind-numbing tasks because you’re worried about having low-level annoyances taken care of perfectly. I’m going to say it: that’s just stupid.


Have a Process

Structured tasks should always be handed off with a process: If it’s something you do regularly, document somewhere like Google Drive, Evernote, or a privately-facing WordPress account (that’s what I use). Anytime you need the task done, just direct the VA or outsourcing service to the process. (This chart is great for deciding if a routine task is worth handing off.)


If it’s a one-off task, your process should take the form of general instructions. You can’t expect the person on the other end to read your mind, so make sure you’re communicating the most important information right off the bat (think it through once). That said, for a structured task, you shouldn’t need to be uber-detailed (see the restaurant example above: that’s about all you need).


Provide Context

And what about unstructured tasks?


Realistically, these will take a little more back-and-forth communication and effort on your part. The difficulty is recognizing when a task crosses the line from structured to unstructured.


For example: I started working with a VA service in the Philippines. The first task I gave them was to come up with a catering menu to send to an Italian restaurant for a party I was hosting at my home. Seems straightforward right? But they just couldn’t get it done. I wasn’t happy with the initial results I was getting, gave them over a month more to fix it, and got no response.


The service wasn’t inherently terrible, but there were just too many barriers (cultural and otherwise) with this task for them to succeed with it. I ended up having to take care of it myself. It was a pain, but not having a catering menu in place for a private party was not exactly world-endingly bad.


I’ve come to learn that with tasks like these, adding more context greatly increased the odds of success. For example: you might think booking a flight should be sooo easy and can’t figure out how a VA could screw it up so badly. But consider every tiny preference and assumption that goes into that: do you prefer aisle or window? Late or early flight? Do you like to fly with a particular airline? Is it important that you get to the airport early enough to get a Cinnabon before your flight? Do you always check a bag, so an airline with bag-check fees is an automatic no for you?


As you can see, there’s lots of room for error if all you were to say was book me a flight on this day from City X to City Y.


Check Your Assumptions

Again, you can’t expect people to read your mind. The more complex a task becomes, the more space there is for personal preference or unique needs: all those little things that you already know and take for granted and assume the other person must already be aware of.


Outsourcing these unstructured tasks can be done, but what’s often needed up front is more fact-finding and codifying of the process. A good VA will ask the right questions to get the context, but you also have to be willing to meet halfway and sit still long enough to give all the answers.


So what kinds of unstructured tasks can be outsourced?

  • Booking travel
  • Creating sales funnels
  • Creating and sending marketing emails
  • General admin tasks like inbox zero or transcribing voicemails for you to read
  • Writing blog posts
  • Website building


It’s all possible: you just need to be willing to put in a little time up front to save a lot of time in the long run.


One more quick and dirty tip?


Lower Your Expectations.

Most VA and outsourcing services bill themselves as the answer to all of your problems. But I’ve certainly said it myself that the charm of pursuit often exceeds the charm of ownership: once you’re signed on to a service, you’re almost definitely going to be less happy with it than you thought you would be while you were getting the sales pitch.


That’s not to say these services can’t help, but you want to start by pushing their edges and finding out where their limits actually lie so you can figure out how to make the best use of them. Treat your first task or two as a test: see what they can and can’t do, how much context they require for tasks that seem easy to you, if the turnaround is as quick as promised. Don’t outsource the ten most important, most complex things you need done right away.


Create a process, provide context, check your assumptions, lower your expectations. Follow these rules, and in no time you’ll be wondering why you ever did any of this yourself.

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