If I’m going to take over the world, I need to learn how to delegate. ;)

It’s a simple matter of mathematics. There are only so many hours in the day. I can’t achieve infinite productivity. Scaling up means figuring out how to work with others and how to delegate.

The traditional way of learning how to delegate involves being promoted to a management role, and that takes time and opportunity. With a little of the money I’ve set aside for my Crazy Idea Fund, I can experiment with delegation and personal outsourcing now. (Naturally, I delegate only non-IBM-confidential things.)

I interviewed almost 10 candidates out of more than 40 who applied. I’ve hired five people on a trial basis and assigned them a few tasks. In the process, I learned so much already! <laugh>

• 80% of success is showing up. Half of the applicants didn’t notice the timezones on my invitations to pick an interview slot, even though I chose a tool that made it easy for them to translate the timezones to their own. And I’d already picked really early and really late times to make it easy for them to fit it into their schedules! Result: Many candidates had to reschedule interviews, and I lost time and sleep while waiting around. Making this better: Next time, I’ll assume people don’t know anything about timezones and I’ll point out the feature for changing timezones.
• I’m a personal-development kind of manager. I’m pretty flexible in the tasks I assign, and I like finding out what people’s strengths and passions are so that I can find the intersection between my needs and their interests. I like how oDesk lets me get a glimpse of how people work, and I offer suggestions based on that. I also encourage people to take some time to reflect on how to make things better.
• I tend to underestimate the time other people need. I find things on the Web really quickly because I’m used to opening a gazillion tabs and using web clipping tools like del.icio.us to store quick notes. I also speed-read like anything. Most people aren’t like that. I need to either scale up my time estimates or help people develop their skills.
• A two-hour chunk is too short a time, particularly considering people are still getting started. I need to give people at least four hours to do a task. Maybe they’ll even get into a flow state.
• I should start with highly-focused tasks or give people more time to become familiar with something. Web research might be difficult for VAs because they’re not yet familiar with the terminology, and I remember how it takes a bit of browsing around to get a sense of what things are called and where to look for information.
• Trying people on a temporary basis is good. One of the advantages of working with small tasks and a structure like oDesk is that instead of betting the farm on one VA, I can try several VAs in parallel and then pick one who’s really the best fit. This is probably more expensive up front, but I learn a lot more because of the variety. After a month, perhaps I’ll decide which VA to work with going forward.

So the next thing that would make this VA experiment better would be to give people a four-hour task (perhaps building on what they’ve already done), and then continue with those who can keep up. I can also reevaluate my budget for the experiment, maybe add some more so that I can give people longer tasks and get a better sense of how people work, and then go from there. I think it’s worth continuing to invest in learning how to delegate, and it would be awesome to eventually build a support structure that can help me scale.

I suspect that after a short trial, I won’t find anyone whose skills will blow me away–but that goes back to what I’ve reflected on before, with employers who expect that people will have all the necessary skills right off the bat.

Yes, some people will figure out what they want to learn and invest time in learning those things. It would be awesome if I come across someone like that – but then I would want them to do more in life than handle other people’s web research and calendars! ;) So in the long run, I think it makes sense for me to invest in improving people’s skills.

Managers and companies sometimes complain that the people they invest in end up moving on. It’s okay if people “graduate” from working with me and go on to do other things. That’d be terrific, and it would give me even more return on my effort! In the meantime, the training materials I build to help people learn how to work can help the next person, and the next person, and so on. In fact, having more newbies go through the system would be great for improving it.

Writing this blog post seems to have fleshed out my reasons for doing this experiment, and what I can do with it… Can’t wait to learn even more!