He's more apt to ask questions before he acts on his own if the boss's attitude encourages it. Knowing what jobs he is to do and what he is not to do is important to the hired man. Let him know what is expected. If jobs are to be done in a certain way or at a certain time, communicate that also. It's better to over communicate expectations than to assume he knows.
Supervision needs to be tailored to the man.
During the early stages of the relations, it is advisable to visit with the employee about how much supervision he wants or needs. As he is able to assume more responsibility, direct supervision can be reduced. A rating of the hired man's performance on a regular basis is a good communication tool. A rating form listing the factors on which he is being evaluated lets him know how he is being evaluated. Factors might include such items as timeliness, avoids waste, safety, job skill, care of equipment, willingness, honesty, pride, use of time, reliability, or other factors pertinent to his job.