I would add in the Do # 2, ask the employee to paraphrase what you're requesting. It's a common problem that people say that they understand what you say, and when the deadline comes, the result is not the expected. I call this practice "duplicate".
Professionals hold back from delegating when they 1) feel it will take to long to teach someone else how to perform the task and 2) fear the task will not be performed to the level they expect. Delegating effectively requires building a team you can rely on. Employees and contractors who consistently show initiative and success in their projects are more likely to be delegated to. Project management programs (ie Basecamp, TeamworkPM and Podio) allow collaboration on projects, while at the same time allowing tasks to be delegated with a clear expectation of deadline.
Delegation of work is necessary and important. The key factors that hold people back are their need for control and their sense that no one else can do what they do as well as they do it. In reality, we have to give up control as delegation is crucial for the success of any venture. There are no large companies today with less than 10 employees because as companies scale they hire people and allocate responsibility to their team.