First thing that comes to my mind is your description of the money in the register in its unorganized state. Somebody (meaning management) has little respect for the money. If they have little respect for it what then can you expect from employees?
Secondly, if you are not part of management and the scenario is of their making then you will be bringing in an element that they obviously don’t care about and they might view as simply an intrusion by you.
Third, it would seem that the problem is essentially not the employee but the philosophy and management style of the business. This particular employee is a symptom and the real problem is management. I would think the “real problem” has to be fixed first because it will be just a question of time before another employee decides to “get their share”.
Many, many years ago I read something that was very disturbing and I did not believe it at first. It went something like this. 25% of your employees are dishonest in some manner and no matter what system you set up they will get you to some extent (money, products, supplies, etc). 25% of your employees are honest because they respond to their own internal set of values undoubtedly developed via their parents. 50% of your employees are honest IF YOU KEEP THEM THAT WAY. So, we have to watch 75% of the potential candidates for theft. Oh, and, when the theft level gets to high the honest 25% group begins to leave because they sense they are in the wrong environment and are uncomfortable. As I said, I did not believe this when I read it. Over the years and through many restaurants I learned it was pretty close. There must be controls and accountability. There must be specific accountability wherever possible. In this case there has to be one person who is specifically responsible for the cash drawer meaning no one else can use it, even the manager. We have done this sometimes even when a particular store environment makes it very difficult to do it until we discover who is stealing. We have even “salted” the drawer with an extra $20 or so to see what happens. If it is determined who the culprit is then they might be terminated because they cannot perform the function of counting money to customers or the drawer at the end of the night. In reality not being able to count change properly, or stealing, should disqualify any employee from handling money.
We have found that stealing is like a cancer. It never remains static, instead it grows however slowly. Somehow employees become aware of what is happening and some begin to participate.
In my opinion we are in a somewhat different era now. When I was a young boy we never locked our house and we could leave tools in the back of our trucks without fear of them being stolen. If my parents ever found something I had which they know they did not buy for me there were questions. When I was very little I went to the market with my father and as we were leaving he noticed I was chewing gum. There was only one explanation. My father marched me right back into the store and made me confess to the manager of the market. I was so embarrassed that I never forgot it all these years. I also did not forget the lecture and the fact that I could not sit down very well the rest of the day. Today it seems in to many instances that there is no particularly negative stigma attached to petty theft. Kids laugh about it amongst themselves and many parents don’t seem to notice or care. Many of those kids are now working in our restaurants.