Legal Question in Business Law in Massachusetts

The problem is that what you are proposing is a deceptive action. There is nothing wrong with your friend providing consulting to your company, but if he is not competent in the technology he is misrepresenting his ability to your company. Likewise, if you are training him in the technology as he renders the service you are engaging in the deception. Likewise, if the company has a policy against you working for others this is a problem as well.

If your friend was already trained even if trained by you, and was competent to do the work the fact he is your friend is irrelevant. Your friend needs to be competent and you can't do the work for him.

In other words, disclosure of the interrelationships to your employer would be very prudent as otherwise you might be fired even if this arrangement is not "illegal" -- and certainly, as Mr. Roth says, if your friend mis-represents his competence and only later learns the skills (the fact that it is from you is only part of the issue), then he has a problem, and so would you if you were assisting in the mis-representation.