When Upselling Hurts: How Too Much Cross-Promotion Can Kill Conversions

Written by Brenda on December 3, 2014 Sell Online.

First of all, don’t get me wrong: cross-selling and upselling, employed in moderation, are extremely useful. As you may know, it’s six to seven times easier, and cheaper, to sell more to an existing customer than to hook in a new one.

But it’s crucial that it be done right.

For example, most eCommerce retailers believe that product recommendations will always increase the number of sales and the profits from them. But that’s not always true. According to an e-tailing group merchant survey, 6 out of 10 retailers don’t actually know how recommendations affect their business. It goes without saying that relatively few retailers are testing and optimizing their performance, as well.

The truth is that product recommendations’ performance depends on how and when you display them. And not everyone gets this right. Cross-selling and upselling are the bane of many customers just because they’re so often done poorly, with the focus put on the business’s aim of selling extra stuff instead of the customer’s aim of making sure the extra stuff will actually benefit them.

Here are some ways that tends to happen and how to avoid them, to boot.

Pushing Too Hard

Like most sales, cross/upselling is a balancing act that takes a lot of skill.

Upselling too hard, or too persistently, can make the customer feel like you’re trying to bleed them dry. And vampirism is never a desirable quality in an e-store.

For example, it’s a dead giveaway when you businesses try to upsell something that’s even more expensive than the original product, especially when it’s unrelated. If someone buys a single album from you, it’s probably excessive to suggest a new high-end stereo to play it on.

Wording also factors into the upsell. Mainstreethost suggests that this might be one field where a softer, more passive wording will actually work better to bring customers around than a direct approach. In the example provided, they compare Staples’ upsell line, “May we suggest some more?” with Amazon’s, “Customers who brought this item also purchased…”

Amazon’s, they conclude, is superior because it doesn’t tell you directly that they’re trying to sell you more stuff. It just tells you what other people like you have liked. It also weaves social proof into the upsell, although subtly, in a way that most customers probably don’t even realize it’s being employed.

Finally, when possible, don’t mention price when you’re presenting the customer with the upsell. You want them to be focused on the value the new offer will provide when combined with the thing they just brought, not the amount of money it will set them back.

Irrelevant Product Offers

Cross-sells are useless if they’re not kept relevant to the initial sell. Consider the story of EConsultancy’s Ben Davis, who was offered website builds and online marketing after trying to buy a t-shirt from Vistaprint, leaving him feeling hustled. Not only that, but he was presented with four pages of upsells after buying, which gave him the impression that he was having the company’s whole catalog forced on him.

The moral of the story? Try to predict the customers’ actual needs instead of just throwing a bunch of products at them in the hopes that one will stick.

Take your time to develop a range of problems and opportunities based on your customers’ priorities. If you’ve done enough analytics-based research, you should have a fairly good idea about what your customers want. Make sure all of your employees know the same, and that any new data or revelations about those wants are quickly communicated throughout the company.

It may help to construct a few different narratives about what the customer’s experience with your store will be, culminating in what he/she would want to buy – directly related to what they just brought – that would make their use of the initial product easier or more convenient. For example, if a customer buys a product that requires complicated assembly, maybe they’d be willing to dish out a little more to have it pre-assembled for them. Or, if they just brought graphic design services for a website, maybe they’d have a use for a web copywriter you know. too.

Using the Same Approach for All Different Types of Products

The overall point of the last section was that customization is a huge part of upselling. The price of your product, its uses, and why people commonly buy them should all be factored into when and how you employ it in an upsell.

If you sell services, then that can often be a different cross-sell entirely, as it’s harder to predict when someone will need something done than when they might be interested in another product. There are some service and specialized industries, like law, where many believe that cross-selling doesn’t work at all. And it makes sense, because unless you get sued a lot, you probably only need one lawyer at a time.

In the realm of more traditional e-commerce stores, your upsells still have to be tailored to your selection, what’s popular, and how other products relate to each other.

For example, if you sell products that come in a bunch of different varieties, like prepackaged foods or electronics, it’s important that you not hit the customer with too many of them during the upsell phase. This is especially true if many of those varieties do the same thing. As a rule of thumb, you should provide them with a maximum of three choices in your upsell offer.

Bonus Tip: Using the Same Approach for All Different Types of Customers

This is a bonus because it’s mainly applicable to client-based businesses, or the ones who have the ability to be discriminating about the specific customers they upsell to in a way most e-stores can’t.

There’s a small segment of customers you want to minimize your interactions with, because their business actually costs you money. These are the people who buy and return, who default on their payments, and who compulsively overuse customer service to the point where the costs of appeasing their demands passes the profit you make from their sales.

Don’t upsell to these people. You don’t want to deal with them any more than you have to. Ideally, remove them from your client list.


The number one rule of both cross-selling and upselling is that the offers should make sense while providing a clear benefit to the customer. The goal is always to create a win-win situation, not to browbeat your customer into buying something they don’t necessarily want or have zero interest in.

Beyond that, they’re like any other sales techniques. They can be done badly or well, depending on the execution. Overusing them, or pushing them too hard, will just annoy your customers and clutter your website. However, when done right, it’ll make a significant difference in both your bottom line and customer satisfaction. And in the end you, your customers, and any affiliates you’re working with will all be better off for it.

Any other tips or tricks you can think of for effective upselling? Any stories about e-businesses that have done it particularly badly or well? If you’ve learned from these mistakes the hard way or have an upsell strategy that really works, please, share it in the comments below!


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