By using this site, you agree to our Privacy Policy and our Terms of Use. Close

The only people I've ever come across who steal from people they know have also had drug problems. Any idea if he's got some sort of vice like that?

I have a pretty good judge of character and haven't dealt with your specific scenario before, but in your situation I would bluntly bring it up and study his expressions when he responds. If there's no sign of guilt regardless of the answer, show him the door. Pick his brain a bit and see what the cause is. Generosity might be a dying trait that few have left, but that's partially for good reason - how do you plan to be a boss when others are taking advantage of you? Know when and where to put your foot down.