The fine line between helpful and harmful

Scott Wiener
Scott’s Pizza Tours
New York City

My first job in the food business was at Chili’s in Clark, New Jersey. As a busboy, I was pretty much working for the waiters. The more of their tasks I covered, the more they tipped me at the end of the night. This meant that I was constantly refilling sodas and chips. I gave so many refills that I wondered how the restaurant could possibly be pulling a profit. Then it hit me: guacamole. The price of my persistent pouring was more than covered every time a waiter convinced a customer to add a side of guacamole to their quesadillas. I learned an important lesson at that job and it resonates with me to this day. There’s an art to the upsell, but the line is fine between helpful and harmful.

The first key is timing. When I step into your restaurant, I’m too hungry to think about anything besides getting food into my belly. You have a major opportunity to direct my attention and control my dining experience. If you want me to order a dessert, just mention it at the beginning of the meal. I’ll fixate on the delicious sounding dessert and set my heart on ordering it before I take down an entire pizza. You’ll probably even get a bonus upsell when my friends order desserts and coffee to enjoy instead of staring at me while I eat the 20-layer chocolate cake you mentioned before we ordered our appetizers.

As simple as it sounds, I feel the need to point out the power of an honest recommendation. I’m far more receptive to “I know it sounds crazy, but I personally love our pickled banana stew” than I am to “We’re famous for our pickled banana stew.” Personal opinion goes much further than the standard shtick because a real live human is taking responsibility for the suggestion. A sharp server will react to my selections and encourage me to amp them up. When I order a standard soda, it’s the perfect opportunity to point out that you offer a unique line of artisanal beverages. I always tell my pizza tour groups how much I adore a Boylan’s root beer with a sausage pizza at Arturo’s in Greenwich Village. At least 25 percent of the group proceeds to order Boylan’s root beers. If I was a waiter and my tour guests were restaurant customers, they would absolutely trust my recommendations on their next visit. What a great way to build customers’ confidence while increasing check averages!

My biggest pet peeve when it comes to servers fumbling an upsell is a disease called TMI (Too Much Information). If you’re just reading a list of ingredients I can add to my salad, I’m probably not listening. My attention span falls off after about three bullet points, so going beyond that is a terrible idea. This world has too many options for everything from toothpaste to telephones and it’s becoming hard to make any decision at all. Keep it simple and you’ll hold my focus.

Upselling requires a delicate balance between being proactive and pushy, but that sweet spot is the key to unlocking the doorway to my stomach.

Scott Wiener owns and operates Scott’s Pizza Tours in New York City.