Business Etiquette: Who Should Pick Up the Check?
Steve Tobak's five rules are good:
The boss should always pay. If there is a boss at the table, even a former boss, he should pay. Many don't but they should. Even if everyone isn't in the same organization, senior level people should definitely offer to pick up the tab. If they don't, they don't just look cheap. They are cheap.
If someone offers, graciously accept. I believe that, when you accept a gift, you honor the giver. I don't know where or when I first heard that, but I've followed it for ages and it's never failed me yet. If someone offers to pay, don't start some testosterone-fueled battle over who should pick it up. Just thank them--and try to be quicker on the draw next time.
If nobody picks up the check, you should. If the waiter drops off the check and nobody goes for it, that's just awkward. The more time passes, the more uncomfortable it gets. At that point, you have two choices: plunk down your credit card or suggest you all split it. I'd do the former, but if you decide to split it, do it evenly. Never get into it over who had what or ask the waiter for separate checks. I don't care if someone had wine with his entrée and you just had a salad. It's trivial. Don't do it.
The vendor usually picks up the tab. In a customer-vendor relationship, the vendor usually pays. That's because her company is presumably on the receiving end of a business transaction. There are exceptions. If the vendor is a small business and the customer is a large corporation or the vendor travelled to the customer's home country, that's a different story. Also some companies have a policy against vendors buying.
Whoever's getting a favor should pay. If someone is making a business introduction, coaching you, or helping you out in some material way, if it happens to be over a meal, then you should pick up the tab--if you can afford to, that is. If it's not over a meal, do not say something like, "I owe you a lunch" like so many do. That trivializes what they've done for you and suggests that's all their time is worth.
Per number 3: Don't dine with anyone you wouldn't happily pay for.
Ha! Excellent point. Cheapness doesn't help anyone.