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Dianna Sanders
32, Woodlawn

Behind the bar: Fridays and Saturdays, plus other days as needed at The Promontory in Hyde Park

Bartending bio: From her very first job serving pizza slices and nachos at a skating rink concession stand as a teen, Dianna has naturally gravitated toward hospitality. “I just think it was intrinsic. My grandmother was an extremely hospitable person. She always made stuff for people, cooked for people …and I assume that it got passed to me,” she said. After a few jobs waiting tables, she landed at the Cheesecake Factory on Michigan Avenue and eventually switched from serving to bartending. She credits the constant churn of Mag Mile tourists and the massive drink menu for teaching her to bartend efficiently. “Efficiency means to be fast and correct,” she said. “They taught me how to be quick, how to be right.” Last fall, she joined the bartending staff at bar/restaurant/music venue hybrid The Promontory and turned her attention to craft cocktailing, training under beverage director Dustin Drankiewicz. “As well as learning how to execute extraordinary cocktails, he has shown me how to be an effective leader and has unearthed a new level of confidence for me.”

Signature drink: Caribbean Cure, a pineapple- and citrus-flavored cocktail made with spice-infused vodka

On expanding her customers’ tastes: “[A customer] might be like, ‘Can I have an appletini?’ And I’ll say, ‘We don’t have Pucker, but we do have Calvados [apple brandy,] and I could make you an apple martini with Calvados if you want to give it a shot,” she said. “I’ve been pushed outside of my comfort zone in a good way, so I feel obligated to do that for other people.” The Promontory’s ambitious drink and food menu has given her the opportunity to nudge people into tasting something new. “You can just tell when somebody wants to try something but they’re too scared to ask you,” she said. “If they see some words [on the menu] that they don’t know … they’re like, ‘What is sunchoke?'”

Drink of choice: Tequila or vodka, the latter of which Dianna is happy to vouch for, even though it’s often deemed a less-than-cool spirit. “Vodka might not have that much flavor [on it’s own], but look at all the things that you can do with it! And to me, that’s awesome,” she said. “I just think people want to do what’s cool, and right now it’s cool to drink craft cocktails made with whiskey and gin. I just like vodka. I’m OK with everyone liking whatever they like.”

Why she loves bartending: “I love interacting with people—the fun of going to work every day and never knowing who you’re going to meet today, who you’re going to see,” she said. “Making drinks is only half of the job. It’s about showing people that you appreciate their business.”

When she’s not bartending: Dianna likes cooking at home and experimenting with recipes. “I’m fairly domestic,” she said.

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