UPDATE: 43Folders has a great article about the psychological barriers to outsourcing, and how to overcome them.

After the initial intrigue, most people that I talk to about outsourcing to a virtual assistant have one common response: “But what would I outsource?” Tim addresses this in the 4HWW book, and here are some additional thoughts based on my experience over the past couple of months.

Thus far we’ve had our assistant find us an apartment, sublet that same apartment, and handle a slew of smaller personal and business tasks. Whether you’re already using an assistant or thinking about trying it out, I hope you find these hints to be helpful.

1. Minimize the kickoff effort.

Set up a single inbox where your tasks will be dropped- it could be a Gmail account, a wiki, TaDa list, CellTell and Jott for quick assigning of tasks, and a special subject line when I send them via email.

2. No such thing as too small

If you have a task that you think will only take you 15 minutes, you might be inclined to just do it yourself. But when you do 5 of those tasks it starts to add up. If you encourage your assistant to use the principle of “batching”, and make sure you follow tip #1, even small tasks can be well worth handing off.

3. Set up recurring tasks

Many things I do each day and week are some kind of “monitoring” task. Again, following batching, these activities are perfect for your assistant to handle. They can filter out all the noise (or lack of activity) and just alert you to important updates. For example, I have our assistant track the Google rankings for my online card sorting application, and keep tabs on the blogs and newsletters of its fans and competitors.

4. Empower them to take further action

Clearly lay out the next steps and you’ll get a major boost in efficiency. Consider the following:

Please find me a good mechanic near my home.

Now compare that to:

Using Yelp and Yahoo, find two mechanics with decent ratings that are located within 10 minutes of my home. Call them both to get quotes on having the oil changed and fixing a tire leak. Set me up an appointment for any morning this week with the one that is cheapest.

I cut the chatter even further by sharing my calendar, and by using an RSS feed to monitor task progress, rather than using email or IM for everything.

5. Dust off that old todo list

Unless you have a full-time team of assistants and a long track record, don’t try to offload your high-stress, high-priority, urgent tasks. It’s a recipe for further anxiety. Rather, scan your todo list (perhaps the ones in your head if needs be) for those things that you want to do but just can’t seem to make time for. Dreamlines (see 4HWW) are a great source for these kinds of tasks. Want to scuba dive off the Great Barrier Reef? There are probably a dozen initial action and research items that your assistant could handle well.

As you can see, most of these are aimed at a goal of minimizing the time you spend managing your assistant and your tasks. It’s easy to end up spending more time in the outsourcing process than it would take for you to just complete the task yourself, which of course defeats the main purpose. With the right techniques and some practice, however, outsourcing will give you more time to focus on the things that bring you the most income and/or happiness.