7 Ways To Upsell Without Sounding Like A Pushy Car Dealer

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Have you ever wondered why your local store always has a bowl of lollies on the counter? Or why fast food workers always ask “do want fries with that?”

When I was about to checkout for a white dress which I bought from an online shop on the weekend, I saw a pop-up asking me if I already had the shoes that would be a perfect pair. I didn’t, so I added it to my cart and paid (I swear it wasn’t the shimmering gem stones that lured me in, promise).

It was when I was waiting for Paypal to finish processing my order that I’ve come to realise that the online shop did a cross-sell on me, and I went for it. 

Did I feel bad? No. 

More often than not, when we hear the words “cross-sell” and “up-sell”, we get the notion of an annoying car dealer trying to make us buy items at ridiculous prices. But it doesn’t have to be that way…

In fact, cross and upselling can strengthen the relationship we have with our customers and give us us more revenue and sales.

Sales guru Jeffrey Gitomer had the perfect response when a reader asked him how he (reader) can to convince the bank to upsell him a new credit card with higher limit – “Tell me how I win. When I win, you win.”


Brilliant, right? If we could make our customers feel that accepting our upsell is a WIN for them, then we’d have no difficulty in cross and upselling.

So how do we do it?!

Okay I know you’re so eager to find out (that’s great!)…  but before I tell you all the juicy details, let us first establish the difference between cross and upselling. It isn’t a lot and both of them are great sales strategies, but for learning purposes let’s get to know them more.

Upselling is a sales strategy that urges buyers to choose a more expensive version of the product he/she is planning to buy; or to purchase add-ons and other features. Meanwhile, Cross-selling is to sell a different product that is related to the chosen product of your customer.

To make this easier to understand, let’s examine the the story I shared with you above….

Selling a pair of shoes after knowing that I’m planning to purchase a dress is cross-selling, because the shoes are a different product, albeit related to my order.

  • Original order: White dress
  • Add – On: Shoes (Another type of product)

Now how do we make that scenario an upsell? It would have been an upsell scenario if they offered me a similar dress and bundled it with my order to get a discount. Imagine this: “Add this dainty pink dress to your order and get save $15”.

  • Original order: White dress
  • Add-On: Dress (The same type of product although a different design)
  • Feature / Benefit: $15 savings if I buy them both

Is everything clear to you now? 
That’s great! As I mentioned, the question isn’t about their difference. In fact, every business should incorporate both strategies into their sales process. The question you should be asking is…

How do you upsell without sounding like a ridiculous car dealer?! For that, I have seven awesome tips for you…

Offer related products

Although offering related products is a given for cross-selling, this should also be the case when doing an upsell. There is a higher chance of conversion when the products you offer them are something they could use with the ones they have already chosen.

For example, let’s take a look at the sales process at Hostgator.com…

When your purchase from Hostgator, it’s given that you either already have a domain, or you’re planning to purchase one from them. So after you choose your hosting package and decide to check out, you’ll have to input your payment / card details and see this:


These additional services from Hostgator gets more sales because these are the things you would need to create a successful website.

Create an easy up & cross-sell process

The one thing that would most probably irk your customers, is if they have to go through the sales process again just because they want to add an item. Remember, it’s YOU who wants their money, so make the experience as customer-friendly as possible.

This is where good website design comes in. Here at Web123, we don’t just create a good design, the business of our clients comes first in our minds, before the swirls and curves we do in Photoshop.

We make sure that before one pixel touches the screen, we’ve already incorporated the basic needs of the business like a well-thought opt-in and conversion path, among others.

Don’t over do it

Also remember that cross and upselling don’t always work to all customers. So when someone decides that their chosen product is enough, give them the option to checkout quick. Don’t bombard them with ‘more things that you might like’, otherwise they might just decide not to purchase anything at all!

We don’t want that, do we?

Sell benefits not features

In our blog post about creating smashing calls to action, we mentioned about selling benefits not features. Why is this the case? The thing is, you won’t be the only one who’ll be doing cross and upselling. So with your competitors doing the same strategies and offering similar products, how do you stand out?

By offering your customers a BENEFIT that’s only available in your store. When you offer a unique benefit, you create “an edge” for you business.

Ask what their pain points are

This is somewhat related to selling benefits, but is so important that deserves its own space.

If you want to know what would push your customers to purchase more of your products, the best way to do it is to ask them directly. Ask your customers what their pain points are, what improvements they’d like to experience from your business, and what things they wish you would offer.

Their answers can be your basis in generating the benefits that you’ll add in the package so they agree to your cross and upselling strategies.

Offer guarantees

One of the most common reasons customers (especially new ones) have second thoughts in purchasing more than one product from an online store is the thought of spending on things they haven’t tested before. To erase this wall between you and your customers, you must make them feel sale in shopping to you.

Offering guarantees doesn’t only add a “safe feeling” to shopping, it shows that you are a credible business owner for believing that your products are of top quality.

Use other mediums

There are a lot of ways to cross and upsell. In fact, it doesn’t have to be in the website / checkout page alone. Email programs, being the highest-converting strategy in the market today, can help you drive more sales.

The trick is to use the tips above (pain points, guarantees, benefits) and incorporate that in your email program to make sure that your customers are aware of the efforts you’re making.

If you’re a small business owner and you are afraid to cross and upsell because of all the false notions about it, stop what you’re doing and listen to me: up and cross selling is not an option, it’s a MUST. They are great business strategies that can help you drive more sales without spending more. 

In the book Marketing Metrics, authors say that the probability of selling to a new prospect is 5-20% while the probability of selling to an existing customer is 60-70%. So do you want to lose this 70% chance of getting more conversion? I bet not!

I hope the tips above will give you a headstart in creating your cross and upsell strategies. If you need any help (this is an honest offer), do contact me right away. I may not respond within minutes, but expect a heartfelt reply in 24-48 hours. 
Do it. Contact me. I’m waiting! 🙂

What do you think? Share your comments below.

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