How to Upsell (Without Your Customers Even Realizing It!)

I tried a new restaurant a few weeks ago. When the waiter stopped by my table, I ordered a hard cider to go with my meal. The next time he checked in on me, he struck up a conversation about the cider I was drinking and mentioned a beer they had on tap that night with similar qualities to the cider I’d been drinking.

“It’s a wheat beer mixed with apples,” he told me, and it was one of their featured beers of the month. “Let me bring you a sample of it.”

I eagerly agreed to his gentle suggestion. And as soon as he walked away, I realized what had just happened. The waiter tried to upsell me. And I didn’t mind a bit. In fact, I even gave him a bigger tip for it at the end of the night. Why? It’s all in the nature of the interaction. Let me break it down for you, because there’s plenty to learn from this waiter’s performance.

Know My Likes

Good upselling starts with paying attention to what I’m buying from you or interested in already. The waiter at the restaurant knew I liked cider – since I’d ordered two already – and made his suggestion of the featured beer based on what he knew I already liked.

Pay attention to your customers’ shopping habits. Our shopping cart integrations enable you to add customers to different email lists based on what they purchase from your website. Or target customers by segmenting them based on interests they tell you about when joining your list. Once you learn what they like, you can recommend other products to suit their tastes and fill their needs.

Start a Conversation

The second pillar of effective upselling is to start a conversation once you know your customers’ likes. The waiter’s job was to sell me the restaurant’s featured beer instead of the cider I was drinking. He could have just stopped by the table, told me they had another featured beer and told me to buy it. But that would have been annoying in the middle of my meal.

Instead, he started a conversation. “Have you tried our apple beer? It’s like cider but it’s a wheat beer, and it’s so good. One of my favorites. Let me bring you a taste!”

It felt like a friend offering me a sip of his favorite new drink at happy hour. If the waiter had taken a hard sell approach, I may not have been as interested in trying the other beer. By starting a conversation with me instead about the drinks I like, his upsell was much more natural – to the point that I didn’t even catch on to what was happening until after he left to get the sample.

Valuable content is more important than a sales pitch and will resonate with your customers much more strongly.

Visit these resources to learn more about starting conversations with your customers through content marketing:
What is Content Marketing?
The Content Marketing Institute
Your Content Marketing Doesn’t Have to Suck

Explain the Benefits

After you get the conversation started, introduce some benefits. In this case, the benefit was the beer’s flavor, which was similar to what I already liked and was drinking.

“Since you like this product, you’ll like this other one even more because of these extra benefits.”

Focus on the similarities first, then dive in to the differences that make the product you’re upselling even more valuable. You want to make sure your customer understands why the other product is equally appealing but better than what he or she already purchased.

Understand When No Means No

Not every upselling story has a happy ending the first time. Ultimately, I didn’t buy the beer the waiter recommended, mainly because the cider I was drinking paired better with my meal. But the next time I visit that restaurant, that apple beer is first on my list of things to try!

The final element of upselling well is understanding when no means no. When I tried the beer but stuck with the cider, the waiter didn’t try to change my mind. But the interaction left enough of an impression on me to want to try that beer at that establishment on my next visit.

If your customers don’t take the bait, don’t force the issue with them. Respecting the “no” nurtures a trusting relationship that will encourage your customers to buy from you again later on.

Do you upsell products to your customers? What advice can you share that’s worked for you?


  1. Howie Nguyen

    10/22/2012 1:57 pm

    One thing I’ve done in the past is to let the customer know that other customers who bought the same thing also bought these other things. Works very well. You also see this being done on Amazon if you browse or buy things there.

  2. Randall Magwood

    10/22/2012 5:09 pm

    I typically upsell by offering a “deluxe” package on some of my products. Prospects can either buy my core product, or they can buy my “deluxe” up-sell product for around $20 more. And they buy it. It’s like two sales for the effort of one. Great blog post.

  3. David kapalu

    10/26/2012 12:46 am

    Highly inspirational blog post on natural marketing techniques. Really got something out of this as well as some blunders to avoid when upselling customers whether new or old.