He'll often have half a bottle of wine over lunch then drive back to the office for a nap at his desk. I feel uncomfortable about this but as I'm new I don't really think I can say anything to him. Yet I'm becoming more and more reluctant to get in the car with him. What should I do?
A: It would be utterly understandable if you chose to do nothing. Raising the subject with your boss when there's no apparently urgent reason to do so must seem deeply unappealing and infinitely put-offable.
But I don't see how I can conceivably encourage you to wait and see: the potential consequences are just too scary. If he gets done for drink-and-driving or, even worse, is involved in a serious accident, you won't find it easy to forgive yourself.
The best I can suggest is that you offer to share the driving. There's no need to imply disapproval or apprehension: your starting point should be one of understanding. You recognise that, for the founder and boss of the company, sociable client meetings are an important part of his responsibilities. In a more extravagant company, he'd have a driver. You'd be happy to take on some of those duties.
If he's at all thoughtful, he must have had a niggle or two about driving after these convivial lunches. With a bit of luck, he'll welcome your suggestion and appreciate the tact with which it's made. At the very least, you won't have left your concerns unspoken and will have paved the way for a second approach if it becomes necessary.