Funny anecdote. At a former company, about 20 of us went out to Dim Sum, expecting to split the bill.
One of my co-workers was from Hong Kong and mentioned that they did this once or twice a week. So being a clueless American, I asked how they handled splitting the bill.
I guess I wasn't too surprised at his response, but he seemed completely puzzled as to why this was an issue. He said they each paid their share, and that was that.
I shared how this is a constant problem for diverse groups in the US, and he basically understood, but thought it was really funny.
My theory as to why this is an issue is that people all have their own preferences around food. What to eat, how much to eat, whether they'll also drink, and how much to tip.
We feel very entitled to all of those. Some people, when offered an all-you-can-eat service, will eat an insane amount of food, while others will eat the same that they would if it were plate-by-plate.
Some will drink if the alcohol is cheap, others will drink twice as much if it's expensive.
Some want just a salad, while others want salad, a main course, and dessert.
Welp, this causes a huge disparity because the bill comes in and either you need to go line by line to get the total, then impose a line by line tip percentage for each person, and, surprise surprise, nobody has cash.
So, how can all this be solved?
Here are a few solutions.
1) If it's for the office, have the company pay for it. This is a really reasonable request. Expense it. It removes any question about who owes what, and removes the sort of grating annoyance of collecting money from individuals. Doing that again and again will wear down a team.
2) Get everyone on board with the same money transfer app, and collect payment immediately.
Use Venmo, or Square Cash, or what ever else is out there. Instant payments make this all go away. If you want to get the app adopted fast, have your company pitch in and send $5 or $10 to each person as an incentive to join up on the same app. This will pay dividends down the road.
3) If all else fails, make it clear up front that the price is going to be split equally, and keep a public log of who has and has not paid – send out an email reminder to the team with the names and who owes what. This may seem extreme, but if for some reason you're unable or unwilling to do 1) or 2) this will make things clear up real fast. If you are concerned that someone on the team can't afford to pay, obviously, don't hassle them, and try to amortize the cost by spreading it over the rest of the team as discretely as you can, or ask a few people who are sympathetic to pitch in offline.
For tools: At my company we use Abacus for expenses, and Venmo for cash transfer.
Amongst friends, we use Square Cash, mainly because one of the regulars works for Square :)