Don’t oversell
Posted: Wed May 28, 2025 5:09 am
5. If the customer seems unsure, offer a free trial or discount
the biggest reason a customer says “no” to an upsell is risk. The cost is too high without a guaranteed return on investment, or they worry about seeing quick time to value. My response is to take away the risk, often by offering a free trial or heavy discount. When there’s no risk, there’s no reason to say “no.” and once they try your product or service and see the value, it will be easier to seal the deal.
i tell my clients that upsells should not increase the total price to the customer by more than 25%. In b2b, this is just small enough of an increase that budgets typically don’t have to be reworked and re-approved. In retail, it’s a matter of perception: 25% more cost for a marked increase in features or quality is a relatively easy sell. (this depends on the business and industry, of course, but it’s held true in my experience.)
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upselling example
here’s a recent example of upselling ripped straight from personal experience:
years ago, i went shopping for a basic pair of new activewear shoes. The sales rep, elaine, didn’t ask the usual “can i help you with anything?” she tossed out a conversation starter: “you look active. What sort of exercise do you enjoy?”
i told her i love to run, but suffered from plantar fasciitis. After a painful course of cortisol injections in my ankles, the doctors recommended shoes with special padding to protect my feet. Even so, i wasn’t sure it was worth the money – i just wanted a basic pair.
Elaine listened, then recommended a pair with arch support that was designed for people with my exact issue. I walked in planning to spend no more than about $100 — a reasonable amount for a basic pair of running shoes — but the $140 shoes she recommended were actually more comfortable and addressed my specific needs. It wasn’t hard to convince me to buy; in a few minutes, i was at the register, ringing up my new shoes and thanking elaine for her recommendation. Upsell successful.
the biggest reason a customer says “no” to an upsell is risk. The cost is too high without a guaranteed return on investment, or they worry about seeing quick time to value. My response is to take away the risk, often by offering a free trial or heavy discount. When there’s no risk, there’s no reason to say “no.” and once they try your product or service and see the value, it will be easier to seal the deal.
i tell my clients that upsells should not increase the total price to the customer by more than 25%. In b2b, this is just small enough of an increase that budgets typically don’t have to be reworked and re-approved. In retail, it’s a matter of perception: 25% more cost for a marked increase in features or quality is a relatively easy sell. (this depends on the business and industry, of course, but it’s held true in my experience.)
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productivity icons like email and chat on an illustration of a laptop with a blue background
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illustrating of einstein character america phone number list surrounded by 3 trailhead badges for ai skills
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upselling example
here’s a recent example of upselling ripped straight from personal experience:
years ago, i went shopping for a basic pair of new activewear shoes. The sales rep, elaine, didn’t ask the usual “can i help you with anything?” she tossed out a conversation starter: “you look active. What sort of exercise do you enjoy?”
i told her i love to run, but suffered from plantar fasciitis. After a painful course of cortisol injections in my ankles, the doctors recommended shoes with special padding to protect my feet. Even so, i wasn’t sure it was worth the money – i just wanted a basic pair.
Elaine listened, then recommended a pair with arch support that was designed for people with my exact issue. I walked in planning to spend no more than about $100 — a reasonable amount for a basic pair of running shoes — but the $140 shoes she recommended were actually more comfortable and addressed my specific needs. It wasn’t hard to convince me to buy; in a few minutes, i was at the register, ringing up my new shoes and thanking elaine for her recommendation. Upsell successful.