There are certain things people are picky about but may not realize. Booking flights is very personal, as it turns out. If you need a window seat at least five rows from the nearest child, you’re probably better off handling it yourself—unless you really articulate the particulars you want, says Ted Roden, founder and CEO of Fancy Hands, which is based in New York City.
Delegated tasks should be small enough that you shouldn't need to check in too often. If it's a longer-term project, agreeing on a check-in schedule up front is better than just popping your head in and saying, "How's that thing going?"
Delegate things that let you focus on the parts of your job that only you can do. "In my case, being a user of my service enabled me to build the company while I continued working my day job, writing a book, and helping care for a newborn," says Roden. "I've been able to operate as a much larger company because of being able to delegate."
You need to give someone enough information to get the task done, but it's not appropriate to tell someone how he or she should do the work. Specify what you need and why you need it, and try to give the person the freedom to get the job done as he or she sees fit.
Delegating is harder than you expect, and it will take you some time to get used to how to work best with members of your team. Even people with the world's best assistants will tell you there was a rough patch in the beginning.