Wilfredo Sánchez and myself, as the unofficial "Cruise Directors" of the Apache Software Foundation, have found ourselves in this role year after year (voluntarily), and having done this at multiple conferences, have learned some valuable lessons about collecting money after the fact for a group outing.
Time and time again, I've seen some poor sap stuck in the "check master" role come up way short of the amount of money owed, and out of fear, wind up eating $100 or more of the group's tab. Typically this happens not out of malicious intent, but out of lack of organization and ignorance on the part of the participants. Should you ever find yourself in the role of this poor soul, here are some tips to make sure that the venue gets its money--and your servers get adequately tipped--without going broke yourself.
- Split the bill evenly: Your best bet for saving your sanity is for everyone to pay "Alla Romana", which means that the amount each person pays is the total cost of the evening (meal + tips) divided by the number of attendees. If someone pulls out a calculator and tries to calculate precise tax and tip for their meal, you have my permission to throw rocks at them (or at least stale dinner rolls). One exception for this is if a few patrons drank a lions share of the bar bill, it's completely fair to ask them to pony up a bit more to cover their part.
- Tip your servers well: If your servers have done a bang-up job of serving your party, tip at least 20%, and make sure you add this into the cost before splitting up the bill. Make doubly sure that the tip isn't already included before slapping another 20% on. But even if the tip is already included, it doesn't mean that you can't tip a little extra if your server went above and beyond the call of duty--remember that it's really hard to serve a large group of people well.
- Round up: After adding the bill and the tip together, divide by the number of people, and round up, not down. If the bill comes to $17.48 per person, round up to $20. If the bill comes to $21.24 per person, round up to $23, or even $25. Odds are that most people are just going to have Yuppie Food Stamps (twenty-dollar bills), so making any change that's not a multiple of 20 is going to require some effort. After everyone has been paid and tipped, you can attempt to get change and give people a few bucks back. If the remaining amount is less than the number of people in whole dollars, consider just adding it to the tip.
- Don't mix up your money: Whatever you do, do not start stuffing people's money into your wallet or, even worse, just pull out the contents of your wallet to use as a bank for making change. This is a fine way to make people wonder if you've turned this into a profit-making opportunity for yourself or, more likely, to wind up spending more of you own money than you should. If at all possible, pay your part first, and pay it in smaller bills that you can use to make change. But basically: keep track of the exact amount of money you've collected, and keep that amount visible at all times.
- Don't mix up your credit: While you can gather all the cash and pay the balance with your credit card, I don't advise this if at all possible--some people might wonder if you're actually paying or if they're collectively paying your bill. I don't care how many miles you get on your credit card, just don't do it.
- Don't be the loan officer: If you're collecting money, avoid loaning anyone money at all costs. This is one more thing to keep track of, and it's a fine role for someone's other friend to fulfill while you handle collecting for the check.
- Be careful making change: If the cost per person is $15, don't let people just start throwing twenties at you and then try to figure out who owes what to whom. If possible, start collecting from people who have exact change and then start making change for others who don't have change.
- Don't fight for the money: You're always going to have one or two people who had nothing but an appetizer and a glass of water and steadfastly refuses to put up a penny more than the menu price of their meal. Fine. Don't argue--they either a cheapskate or they genuinely can't afford to shell out more money. If it's the former, making a big stink is going to make you at least one enemy. If it's the latter, making a big stink can potentially make you many enemies. Basically, there's no way of winning here, so you can use some of the extra cash you came up with when you rounded up (you did round up, didn't you?).
- Don't play credit card poker: But more importantly than that, don't let individuals start paying with credit cards. Beg them to go to an ATM or to borrow money from the guy next to them, but nothing says "screw you" to a waiter more than a check folder with half a dozen credit cards in it.