One thing to know: the most senior person at dinner always picks up the tab regardless of whether or not he is reimbursed. If you are not sure if you should pick up the tab, you are not the most senior person.
What if I’m out with peers? Well, it’s probably not an official business dinner. Peers don’t talk business over dinner. They do it at their cubicles.
What if my boss if my friend? Am I not clear? Your boss should pick up the tab. Always. Even if it seems like a social, no-stress dinner. It’s work. Your boss pays.
What if I have dinner with a former boss? Bosses should always pick up the dinner tab when eating with a former employee. Always. When I go to lunch or dinner with my former bosses, I never pay. And when I eat with people who reported to me, I always pay. Some of them are doing quite well but it doesn’t matter. I know the rules. I always pay.
I’m not a boss. Is there ever a time when I pay? Yes, you pay when you eat with your friends or your peers. You can also tell your boss — it’s your birthday so I’m treating for lunch. That works.
This seems hierarchical, Laurie. The business world is hierarchical whether you know it or not.
Our company’s culture is different. Yeah, that’s cute. It’s different until you make money. When you have no money, everyone pays their own way. When there’s a round of cash or a good quarter, bosses get generous. When a company matures, rules are in place to help people figure out when it’s on the company’s dime and when it’s on your own dime.
Business dinner etiquette is meant to help you from making a fool out of yourself. Now hand me the bill.