I’ve been in the corporate world for a few years now, and I’ve encountered some normal-but-kind-of-awkward lunch situations. Who orders first? Are we planning to stay for a while, or make it quick? I’m always a little weird when it comes to who picks up the check, particularly in a situation where most of the parties are “equal”. So, I figured I should write a post and see what the rest of the corporate world would do in these situations.

The company lunch. This one isn’t as awkward about picking up the check, as it’s highly likely that the most senior member at the company lunch will take care of it, and let you know well in advance. The awkward part here is knowing who picks the table, who orders first, and how long you’re staying. Theoretically, the most senior person who’s paying would make all these choices, but this has not been my experience. In a male-dominated field in the South, most of my bosses and colleagues try to be gentlemen by letting me walk in front, order first, etc. This is really awkward, because it means I generally have no senior person to set the price point or length of stay. Should I get the soup or the steak? I know they’re trying to be nice, but it puts me in a weird position because I’m technically not the person who should be setting the tone for the meal! I’ve been trying to deal with this by immediately asking a more senior person what they usually order, or what sounds good to them. This usually helps pin down a price range and length of stay, and I think it comes out pretty naturally vs. “Yeah, I don’t know how this lunch is supposed to go, so can you tell me?”

The colleague lunch. This one is a little more dicey regarding who picks up the check. Again, old-school etiquette would either advise that the most senior person pick up the check, or that the person who initiates the meal picks up the check. But what if you’re both equal? And, what if it’s not really a formal invite, but more of a casual meal? For example, when I attended the tradeshow, I ended up spending most of my time with a more senior colleague from a different department. This colleague is not my supervisor, and rarely works with me, so he’s only “senior” by tenure at the company. We both have to fill out expense reports, and we both have to eat and make it to the show floor. Who pays? He said that generally the most senior person picks up the check, which would be “standard” business etiquette. What about when you have three senior people who are all the same level, but in different departments? I still haven’t figured out a graceful way to determine who pays in this situation, or who orders first to set the tone. Again, the soup or the steak? The $5 quick meal or the $30 stay for hours meal?

The client lunch. This one should be pretty easy, as the company representative would usually pay for the client’s lunch. But what happens when you’re the client, but the person inviting you is basically on the same level? My issue here is that I’m not really the final decision-maker, but I am a very valuable gate-keeper. If your offering doesn’t meet my standards/instructions, it doesn’t get sent over to the final decision-maker. All else being equal, I do get to make the choice between two or three items that meet the standards from the decision-maker. So, you do want to keep me happy… but happy enough to invite me to lunch? Or, are we splitting it, as a “friendly” way to have a much-needed discussion in-person, without the boring office atmosphere? I think this situation qualifies as quasi-client, which makes things much more muddy.

So, for those of you who’ve been in the corporate world for much longer, how do I handle these awkward situations? Am I the only one that thinks it’s awkward? Is it just a lack of experience?