Thursday, November 5, 2026

Upsetting the Upsell


Brands that choose upfront selling over upselling will attract a loyal following.

One of the challenges of being a student of business and a marketing practitioner is the voice in the head that starts analyzing a sales process instead of the actual product being purchased. Every sales person is my teacher, and I deeply respect their craft.

On a regional flight in India once everyone was seated, a salesman appeared out of nowhere, made a poetic sales pitch for gift items and then disembarked. It was entertaining and captivating. It was like a commercial one can’t rewind. I have never seen it happen again.

Sales pitches were (and still are) common in the commuter railway trains in Mumbai, with sales people darting between railcars. The raw fast sales pitches aren’t the choreographed sales processes one encounters at a car showroom. These sales folks were brash, extremely confident about their product, adept at crowd-work like a stand-up comedian and they challenged any passenger who made eye-contact to also make a purchase.

On the one hand, there’s the case of the unvarnished sales process where what you see is what you get, and on the other, at a car dealership, is a convoluted process, steeped in guesswork, the fine print, and a ‘gotcha’ finale.

Just when you think you are done comes the upsell for which we must brace ourselves because there’s a giant digital touchscreen that makes the surface of a desk displaying lots of words, lots of screen-swiping, many digital signatures all done over a running commentary on how Grandma purchased a certain extended care package and has now attained salvation.

For a first-time buyer this can be a painful and worrisome experience committing to a ten percent increase in cost for services they will never use, and should they ever need them, the fine print with exclusions will get them.

For the experienced buyer, all it takes is tremendous patience to say “No” to every upsell ask, and alertness while digitally signing on the several pages.

The irony is that as soon as the last signature is done, the sales personnel seem to be trained to be cold and rude. It’s a transactional relationship. That is short-sighted for any brand especially in an age of instant and effortless broadcasting of a purchase experience.

Car dealers can do better and make their own lives, and those of their customers, way easier.

List all the extras you will try to upsell beforehand. Anchor the higher price point in the customer’s mind while also anchoring the value of the entire package. Let the customer visualize worry-free ownership at the outset. Be upfront in everything the customer can buy. Expect your customer to have already done the research. Focus on building a relationship with your customer’s personal network. Do not upsell. Your customer is also effectively your distribution channel. Earn their trust by being upfront about everything you can sell. The upsell is overdue for an upset.

Pic credit: Rob Dean via Unsplash