A few weeks ago there was some discussion online about hiring virtual personal assistants to help offload non-essential business tasks. Around that same time a Twitter user messaged me (and quite a few other indie devs) asking what sort of business tasks we would consider outsourcing. I'm pretty sure this industrious @replier was just looking for job leads, but it did cause me to stop and consider what parts of my business would I be comfortable delegating to an assistant.
The short answer is, not much.
For developers of a consumer-oriented product I think there might be a strong possibility of being able to hand off documentation writing and lightweight customer support. It would be great if I had someone answering emails that only required a link to an FAQ article, leaving the truly in-depth questions for me to answer.
But for a technically niche product like VirtualHostX, I worry my non-specialized assistant wouldn't have the technical chops to answer anything but the most basic support questions. Writing documentation would likely also be a problem. However, if they've used the software proficiently in the past, the thought of them editing together some instructional screencasts is very appealing - as that's something I never find the time to do myself. I'd love to build a list of topics and then have them go off and come back with screencasts ready-to-go. I'd easily pay a few hundred dollars a-piece for that service.
So while I'm not comfortable outsourcing my core business tasks, I have begun delegating personal tasks to free up more time for the business. A few months ago I signed up for Fancy Hands. For a few bucks a month I have access to a network of virtual assistants that I can send odd jobs to. Basically, anything non-confidential that can be completed electronically and/or remotely is fair game. I've used my assistant to schedule appointments, cancel hotel reservations, price shop, and do online research. I've been very pleased so far.
At first I found it difficult to come up with tasks to delegate to the service. A week or two would pass and I'd suddenly think "Oh, crap. I haven't tasked them with anything lately" and worry about not getting my money's worth.
So, I created an "on hold" context in OmniFocus called "Fancy Hands" just like I would create for any other person I assign tasks to. Then, during my weekly review or when I'm flagging tasks for the day, I'll consciously keep an eye out for anything I can assign to them. This helps with remembering to delegate tasks as the possibility of doing so is forefront in my mind.
I don't have any big conclusion or take-away. These are just my thoughts after actively trying to learn how to delegate tasks while running a one-person company.