How to Upsell as a Server - The Right Way

As the chief dining critic at “Chicago” magazine, I spend more time with waiters than I do with my parents. I know all of their tricks and every weakness they try to hide, but never quite can. 

If your staff thinks the menu is a joke and the executive chef is a shameless ego merchant, I know this before the first course arrives. If your employees despise their customers, they give it away before water is even poured.

And I certainly know when a server is trying to upsell me. “Oh, you’re interested in that cabernet ($34)? Well, then you’ll love this pinot ($46).” 

I know what you’re doing. Maybe you don’t care that I know. You’ve got percentages to make. But you’re treating me like your personal ATM, interchangeable from the ATMs seated at the next table. I don’t want to be treated better than the other guy. I want to be treated like I’m not interchangeable. And—news flash—I won’t be back if I feel manipulated. Nor will I encourage diners to check you out. 

Short of blatantly rolling your eyes and sighing loudly, there is no quicker way to alienate a diner than by cynically trying to squeeze an extra couple of dollars out of them. 

So why do some operators allow this kind of service? “A lot of places upsell because they don’t care,” says Matt Schneider, general manager of Celeste in Chicago. “They don’t train their staff right, or train them at all. There’s a level of disdain on their face that they have to serve you. Any customer can sense that right away.” 

Others attempt to upsell through false camaraderie, which grates even more.

But the good servers, the ones who know how to lead without alienating me, can point me toward the priciest dishes and I listen. How do they do that? Let’s go back to basics. Once mastered, it’s not upselling. It’s good service. 

Know the Menu

“Knowledge is the base for the upsell,” says Obadiah Ostergard, president of Au Bon Repas Restaurant Group in San Francisco (Claudine, Gitane, Gaspar Brasserie). “If the waiter has that natural knowledge, it’s an organic conversation.” That waiter doesn’t shift into auto mode when asked for advice. 

He has more than just a surface understanding of the offerings and can make informed recommendations rather than rote ones. A good bartender would never say, “Would you like a shot with that beer?”

“He’s not just going to sell you a shot,” says Schneider. “He’s going to sell you the right shot.”

Read the Guest

The best servers change their service according to each table. They’re tuned in to their customers’ body language, and not just the obvious stuff like the couple with an early show to get to, or the group eternally huddled in conversation. They sense if the guest wants to lead the experience or be led, and they adjust accordingly. Diners notice the personalization. 

“The ultimate goal is to read your guests and understand what they want from the experience,” says William Douillet of Atera in New York. “At that point, your server can sell anything.”  

Think Big-Picture

Upselling goes beyond the here and now. “The smart upsell isn’t just pointing out higher-priced items,” says John Burke, general manager of Zocalo in Kansas City, Missouri. “It is making sure the guests return again and again.” 

Instead of fixating on selling that extra appetizer or dessert, Burke works to create and maintain an environment that “supports the overall selling effort.” 

If the restaurant and staff play the part, customers will be comfortable spending more. In turn, servers will work to keep the restaurant looking and feeling great. 

Get Creative

In many restaurants, money is the subtext to all conversations between staff and customer. It is a give-and-take that Brad Bolt, managing partner of Bar DeVille in Chicago, calls “the dance.” Bolt encourages his staff to engage in a dialogue with customers and gauge their interest without pushing. 

"Patrons like stories because it deepens their appreciation."

-Obadiah Ostergard of Au Bon Repas Restaurant Group

“You feel them out,” says Bolt. “What do they want to spend? Then you let them know why it costs what it costs, and there is a good reason for it. Upselling works as long as there is a perceived value.” 

If you can figure out different ways to broach the subject, go for it. Bolt worked with a waiter who routinely asked customers, “Do you feel like driving a 3-series, 5-series or 7-series tonight?” It worked, because the guy connected with his guests. 

Translate the Kitchen’s Passion

It’s not enough to love the food coming out of the kitchen. A server needs to be able to say why it’s good, which starts with understanding how it’s made. At Gaspar Brasserie in San Francisco, pastry chef Charles Dugo constructs a strawberry and pistachio French wedding cake with pistachio mousseline and toasted financier. Its production is time-consuming and intense. 

“It has a great story and we make it clear that it’s an amazing offering that’s not to be missed,” says Ostergard. “Patrons like stories because it deepens their appreciation.”

Put Yourself in My Shoes

The best service is rooted in empathy. A server should essentially say: "I know everything there is to know about this restaurant, and this is what I would do if I were you." 

If that service can be established, upselling feels less like a server-guest dynamic, and more like two friends sharing a conversation about a great bottle of wine.

“Once complete confidence is achieved, servers can be themselves—they can be riotously funny, they can break rules, they can be passionate and compelling,” says Douillet. “Then it’s up to the server to put your money where their mouth is.” 

Jeff Ruby is the chief dining critic for Chicago magazine, a freelance writer and author.