I am often asked whether there is a danger that providing too much oversight and engaged management will keep employees from developing their ability to manage themselves. The answer is no. In fact, the only real way to help employees get better at managing themselves is to manage them well.
First: By managing an employee very, very well, you should be exemplifying, demonstrating, and teaching many of the same methods the employee will need to apply when it comes to managing himself.
Good self-management (just like good management) revolves around a regular ongoing accounting: What is expected of the employee? How is the employee's performance measuring up to those expectations? What can the employee do to improve? What does the employee need to revise and adjust?
And good self-management (like good management) requires one to regularly clarify priorities; clarify expectations; clarify plans; clarify action steps; clarify timelines.
Second: By managing the employee very, very well, you should be teaching the employee what to do and how to do it. On a whole range of tasks, the employee should be learning through sheer repetition: The employee should be learning guidelines, specifications, and standard operating procedures.
Third: By managing the employee very, very well, you and the employee are likely to be creating tools (like checklists) that should help the employee become more self-managing.
Fourth: By managing the employee very, very well, you should be gradually expanding the employee's scope of responsibility. This means bigger goals or bigger constellations of goals. This means longer deadlines. This means you are stepping back, meeting every other day instead of daily; meeting once a week instead of every other day.
Fifth: By managing the employee very, very well, you should be teaching the employee good work habits, such as good time management, organizational skills, interpersonal communication skills, and critical thinking/problem solving.
Sixth: No matter how good your employee gets at managing himself, remember, he still needs you. If not, then you shouldn't be his boss anymore.