When in Rome?

The first problem is the language barrier. Make sure they are very fluent in Italian before going (or pay for interpreters). The second (and bigger) problem is the culture barrier. European customs are different to U.S. customs and this is particularly relevant in terms of business. I am English and many of our businesses and utilities now have American owners. They attempt to do business here the same way it is done in America and it doesn't transfer well in certain cases.

The American model often seems to be to build something down to a price and the cheaper it is, the better, because that means it's more commercially viable and more people can afford to buy it. In certain industries (the food industry springs to mind) that really wouldn't work in Europe. Price is much less important than quality, simplicity, and that something has been produced in a natural way or traditional way. I'm not saying either system is better or worse, just that each system works for each environment.

As for your other issues, I'd be specific about the people you send out to Italy. I'd pick people who are open-minded, keen to learn about a new culture, tactful, and politically wise. The Americans I've met in my own country and that I count amongst my friends have all had these traits and integrated well in about six months. For the first six months they said they felt a bit lost by our customs, humour, speech patterns. Italy is more of a culture shock than England. Italians really can be what appears to be temperamental and hot-headed but they are also very generous, family-minded and traditional (which are American traits too).

In terms of returning to America, I don't see any problems. Although, from experience, you may find they miss Italy and may want to return. When you live in a different culture (particularly one as strong as the Italian culture), it can become part of you. Even the little things. You may think you know what bread, coffee, pizza, or ice cream tastes like. I thought I knew too. When you go to Italy, you know what it's *meant* to taste like. I judge food in my own country very harshly now even though English restaurant food has had a revival and is some of the best in the world. What you may notice is that your staff come back full of the joys of Italy and seem negative about certain things in America. But then, if you're in imports/exports, you can import the stuff they fall in love with!