The restaurant world may still be divided in the tipping in restaurants debate, with some eliminating it altogether and others bringing it back. But until the issue is sorted out for good, servers hustle to make the most of each table, and learn how to be a good server. And since not everyone can bank on a generous celebrity walking through the door, we asked for the best server tips and tricks that helped earn them their most memorable pay-outs. Here’s what they had to say.

Know the VIPs

Matt Ormsbee, formerly a waiter at Foster’s Boiler Room in New Hampshire’s Common Man Inn, attributes his largest tip60 percent on a party of more than 20 gueststo identifying the key players at the table and providing extra special service.

A rehearsal dinner of more than 20 was seated in his five-table section, so in addition to keeping waters filled and pre-bussing the tables, Ormsbee said he catered to the bride and groom, and, perhaps more importantly, the parents who were footing the bill.

“The most important thing with a party like that is knowing who is most important. Pay special attention to the bride and groom, but pay extra special attention to the parents of the bride and groom,” he says. “I was tipped 30 percent on the credit card, but then the father of the bride tipped me 30 percent again in cash.”

He says engaging in the group’s celebratory vibe can always help. “They are coming to your restaurant to celebrate a happy occasion, so you have to meet them where they are with your mood,” Ormsbee says. “They are happy and ready to celebrate, so you are happy and ready to celebrate.”

Restaurant manager talking to customers at their table

Read the table

Understanding the mood of the table is just as important for being a good server when there isn’t something to celebrate, notes Chuck Tyler, who stresses the importance of unintrusive service when the time calls for it. He received a tip of more than 50 percent while going as unnoticed as possible while waiting on a table.

“The table was clearly conducting business,” Tyler remembers. “They were at the table for almost two hours. I manicured their table as needed, noted the occasional glance, and appeared as often as their body language indicated.”

Always listen

A slow Tuesday day shift turned into a memorable afternoon for Ksenia Newton, who was working as a bartender at a bar by Wall Street when a lone customer tipped her $600 after another staffer didn’t feel like engaging in a lengthy conversation.

“It was understandable. It’s morning, and the last thing you want is talking,” Newton says. “I was bored, so I let him talk. And boy, he did. He talked for a little over an hour, complaining and relieving his stress related to the current stock market situation, stress around his wife. At the end of the monologue, he thanked me for listening, gave me money and told me that this was much cheaper than what he was paying his therapist.”

The moral of the story, she says: “Always listen to your customer.”

Make a special connection

Janice Holt struck up a meaningful conversation with one of her customers at Abe & Louie’s in Boston, mentioning that she worked as an art teacher in a middle school. When the guest inquired about the biggest supply needs, she told him that she had to buy watercolors out-of-pocket because they weren’t provided.

You can control the conversation and change the way guest communication is handled with proper staff training.

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“Along with tipping me on the bill, the guest wrote me a check specifically to cover a year’s worth of watercolors for my art room at school. It was a few hundred dollars,” Holt says.

And it didn’t end there. “He then came back yearly to sit in my section and continued to write a check to me for the next few years for watercolor supplies so that I would not have to pay for them. I will never forget that kindness,” she says. “At Abe’s, we stress the importance of having a personal connection with the guests, and I try to do that with every table that I serve. I think it was that level of service that moved him.”

In Dallas, Christine Smith-Lueders has earned several $50 and $100 tips during her 30-plus years in the restaurant industry, so she speaks from experience in advising fellow servers to show how much they care, whether they’re working in a fast food, casual or fine dining environment. One night, a widow dining out on her anniversary tipped $50 for Smith-Lueders service, even including a note.

She even became the unofficial member of a marketing team while working at Bennigan’s in Dallas when she overheard a group coming up with a toothpaste commercial and started laughing. “I told them how an individual might take that pitch in a different way than they intended,” she recalls, and her candor stuck with them. “They met me every Tuesday at 3 pm and pitched me different items to get real feedback. I earned $100 every Thursday.”

Making that connection literally pays off, Smith-Lueders explains.

“Listening and making people feel special, making a connection to them, and making sure that what they ordered is wonderful and correct,” she says, “is what helps servers make more money.”

busy bar

Always have a trick up your sleeve

Erik Dobell may currently work as a mentalist and magician, but it was prior to this career, while he was waiting tables full-time that he earned his most memorable tip of $100 on a $30 bill when he entertained a fussy child.

Food for the family of five was taking longer than usual, Dobell remembers, and the 5-year-old daughter was starting to act up and cause a scene.

“I decided I’d try a little magic for the table. I rolled up a few napkins into balls and then made them disappear and multiply,” he says. “I ended up doing a small card trick for the whole table, and then the food finally came out.”

While the rest of the meal was uneventful, Dobell says the family left him the tip and a note, thanking him for taking the time to cheer her up.

Check out Upserve’s guest communication guide!

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Meghan is an award-winning journalist and content marketing manager who lives to tell stories. Her favorites include highlighting all things restaurants, from front-of-house hospitality to back-of-house grit. When she's not writing about them, you can find her eating her way through Providence and Boston searching for inspiration with a rye Old Fashioned in hand.