The biggest mistake I see people make when they start the process of delegating to an assistant or team member is to start looking for things that they can delegate.
The mistake is understandable. If someone asks you, “What can I do for you?” your first instinct would probably be to scan your to-do list for something that seems delegatable. But for long-term, effective delegation, don't begin by focusing on what you want to hand off.
Begin the process by determining what it is you want to do.
Forget about the rules you've heard about what you “should” delegate. There is no “right” set of tasks to delegate, and there is no “wrong” kind of task to hand off. What matters is what works for you, not what works for anyone else.
If you really enjoy keeping your own books, do so. Bookkeeping is often one of the first tasks a small business owner delegates to someone else–but it doesn't have to be. If you like setting up and coding your own newsletter, then continue to do so. You get a creative charge out of looking for images to use in your blog posts? Then keep doing that. The tasks that others “usually” delegate might not be the ones you want to get rid of, and that's fine.
Don't plan on delegating those tasks that you love doing.
Folks often get frustrated with delegation because they try to delegate tasks they believe they ought to hand off, regardless of their own affinity for doing those tasks. Those tend to be the tasks that they later say their assistant or team member could “never do well enough.” The delegator's perfectionism sometimes stems from the fact that they tried to delegate a task they really loved doing themselves. So if you love it, keep it.
Start noticing what isn't on your “I want to do this” list
The tasks or steps that really bug you or that you downright dislike are often good ones to hand off to someone else. Those also tend to be pretty obvious to us. If you hate making and remembering appointments, it's usually not too difficult to think of delegating your calendar management to someone.
What is sometimes less obvious is a task that we don't necessarily loathe, but also doesn't make it onto our “I love doing this!” list.
For example, maybe you're a photographer who doesn't mind the process of uploading & placing photographs on your website, but you do it out of necessity more than enjoyment. You could delegate that.
Or perhaps you're a blogger who always formats your own blog posts and comes up with post titles, but your core passion is the writing. You can delegate the formatting and titling.
Or maybe you love giving teleclasses but, when you stop and notice it, you realize you get a bit stressed out over setting up the pre-call reminder emails and managing the web interface during the call. You can delegate those.
Chances are the tasks you do don't all fall neatly into two categories: “Love” or “Loathe.” There are probably a whole heap of tasks that fall into a middle spectrum, somewhere between “This is okay but not awesome” and “This doesn't totally drive me crazy.” All of those middle spectrum tasks can be great to hand off.
Reframe delegation so that it's less about getting rid of stuff from your to-do list and more about supporting you doing what you love
Rather than confining your delegatable tasks to those you dislike or don't know how to do, look at delegation as a way to make more room for you to do the really high-value tasks–the stuff that lights you up.
Rather than looking at your assistant or team member as someone who does stuff you don't want to do or can't do, see that person as someone who allows you to do more of whatever it is you love.
Rather than approaching delegation from the perspective of wanting to offload things from your to-do list onto someone else's, approach it from the perspective of wanting to fill your to-do list with the stuff that lights you up, and letting your team member(s) support that endeavor by handling the rest.
When approached from that perspective, the process stops being about what “should” or “shouldn't” be delegated, and starts being about what lets you flourish. (And isn't that really the whole point?)
The process of delegating and working with a team member is personal and unique–just like your business. Delegation won't look the same for you as it does for your business mentor or your good friend or the other person who uses the same VA you use–because you and your business aren't carbon copies of them and their businesses.
So the only way to know whether a task or project is best-suited to you or to your team member is to determine whether it lights you up, or whether it's something that supports your doing the things that light you up. The former activities constitute your domain–the latter are the ones your team member can run with.
What supports you in doing what you love?
What kinds of tasks or projects do you do that aren't really what you love doing, but support you doing it? What sorts of things do you ask for help with–or what would you love to ask for help with but haven't yet? (If you have worked with an assistant or team member, what did you delegate that supported you, and what did you try delegating that didn't end up working out at all?)