When delegating work, what are issues that might arise? How much direction should be given? How does a manager discontinue obsolete reports?

When delegating work, what are issues that might arise? How much direction should be given? How does a manager discontinue obsolete reports? If a manager delegates a job, how can he/she be sure that the employee understands that the boss is not just dumping work he doesn't want to do? How do we empower our employees?