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How To Upsell A Customer Without Being Pushy

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Upselling your customers doesn’t have to be manipulative. Here’s how to do it right.

I know, I know.

As soon as you hear the word “upsell,” you might have some less-than-positive reactions.

“Gross,” you might say. “That’s sleazy. It’s dirty. It’s manipulative. And it doesn’t work.”

You’re not alone; a lot of people think that upselling is a dirty word, and that upselling your customers is only going to make them like you less.

Well today, we’re going to set the record straight.

Here’s the thing: if the only experience that comes to mind when you think of upselling is the pushy car salesman or the cashier at Best Buy reading you the lame scripted upsell for an extended warranty that you don’t need, then of course you won’t like the idea of it.

Many of us have been burned and mistreated by upsellers more focused on making a buck than helping us succeed, and that leaves a mark.

But it doesn’t have to be that way.

Upselling can actually be an incredible tool that doesn’t just drive more revenue—a lot more revenue—for your business; it can even help you build better relationships with your customers.

Upselling Can Bring You Closer to Your Existing Customers

Sales guru Jeffrey Gitomer puts upselling into perspective when he describes it as helping your customers win.

A reader asked Jeffrey for advice on how they could upsell him on a credit card product that was more expensive (and more valuable) than the one he currently used.

His simple response?

Tell me how I win. When I win, you win.

If you can make your customer feel like an upsell is helping them win, then you’ll both win.

Here’s an example: a couple of years ago, I checked into a hotel on a weekend trip with my wife. As we were checking in, the clerk offered me an upsell: would I like to add breakfast for two—normally $49—to my room rate for “just” $29?

I accepted without hesitation, and I was happy to do so. At $20 cheaper than the standard rate, I felt like taking the upsell offer was an easy win.

From the hotel’s perspective, they upsold me on additional services that I otherwise would not have purchased, made extra profit, and built a deeper relationship with me, as that breakfast is one more opportunity that they’ll get to serve me.

A clear win for them, too.

Learning How to Upsell Right Can Also Deliver Massive Benefits to Your Business

In addition to the customer loyalty upside of upselling in customer service, there’s also the bottom line benefit.

In the book Marketing Metrics, the authors share a fascinating finding from their research:

The probability of selling to a new prospect is 5-20%. The probability of selling to an existing customer is 60-70%.

That’s a big gap.

But when we think about it, it really shouldn’t surprise us.

Wouldn’t we much rather buy from a company we already trust than one we’ve never done business with before?

Not only is upselling easier than selling to a customer for the first time, but it can help you grow faster.

Upselling Doesn’t Have To Be Pushy

Even if we know that upselling can be extremely valuable, many of us, scarred by scammy upsell offers in the past, still don’t feel “right” doing it.

But with the right timing and upselling techniques, those unpleasant upsells are actually very easy to avoid.

It all comes down to when and how you upsell, and below are some tips and examples for both.

WHEN to Upsell

When it comes to successful upselling, timing is (almost) everything.

There are three “triggers” that are particularly powerful:

1) Immediately after the customer gets value from your business

Chris Yeh, an investor, entrepreneur and the VP of Marketing for PBWiki, shares a great example of a well-done support upsell when he called Geico for roadside assistance.

After providing GEICO with my location and arranging to wait for the tow truck, the GEICO dispatcher told me, “From looking at your account, it looks like you’re now eligible for a big discount on our comprehensive coverage. Since you’re going to be waiting for the tow truck anyways, would you like to hear more?”

15 minutes later, I had agreed to add $1 million in additional coverage for my car and home, at a cost of right around $100 per year.

I’ve been a GEICO customer for 16 years already, so it’s not much of a stretch to speculate that I might be a customer for another 20 years. That means that GEICO turned a costly customer service call into an incremental $2,000 in lifetime revenue.

Because Chris’ upsell came at the time where he was “feeling” the value of being a Geico customer, he was far more likely to happily say yes.

2) Immediately after the customer decides to buy

If you’ve ever been asked, “would you like fries with that?”, then you’ve experienced these types of upselling strategies.

One of the hardest things to do is to convince a customer to buy from you; once you’ve made the case that your business is worth buying from and the customer pulls out their credit card, they’re showing that they’re ready to buy; this is a great opportunity to add additional value.

This approach is commonly used with “shopping cart upsells,” like this one from 1-800-Flowers:

Getting a customer into “buying” mode is hard. But once you’ve accomplished that, it’s easier to open the door to a deeper relationship.

3) Immediately after the customer achieves a milestone

Another popular and effective time to upsell your customers is when they’ve achieved a milestone in doing business with you, like:

Use these events as opportunities to remind your customers about the value they’re getting from doing business with you, and think about how you can upsell them now to take things even further.

The Two Rules of Upselling

There are two rules to remember about upselling your customers:

1) Make sure they’re happy with the service and experienced you’ve delivered to them. NEVER sell to an angry, upset or disappointed customer.

There are a couple of useful options for singling out customers who are happy.

You can use labels in your help desk software (we use Groove, for obvious reasons) to tag customers who are “fans.” That way, when a fan emails you and you sense an opportunity for an upsell, you’ll already know that they might be open to it.

Another equally effective way—we use both—to identify happy customers is with Net Promoter Scores, one of the most important customer service metrics.

The Net Promoter Score Survey, sent to your customers regularly (you can use an app like Promoter.io that does this for you), asks two simple questions:

Results from the first question tell us how many of our customers are promoters (those who respond with a 9 or 10), passives (7 or 8) and detractors (0 to 6) of Groove. Results from the second question tell us why.

While this data can help you make better decisions on a number of fronts, knowing who your promoters are is especially helpful for knowing who to target your upsell offers to.

2) Focus your upsell pitch on how the customer wins.

Remember how upselling works best when you tell the customer how they win?

Here’s that quote from Jeffrey Gitomer again:

Tell me how I win. When I win, you win.

While this is great advice for any sales, focusing on how you’re helping the existing customer win even more is absolutely critical for upselling without being pushy.

In Chris Yeh’s Geico example above, notice how the support agent framed the pitch very clearly around how Chris can win:

From looking at your account, it looks like you’re now eligible for a big discount on our comprehensive coverage. Since you’re going to be waiting for the tow truck anyways, would you like to hear more?

The agent could have started with “would you like to hear about our comprehensive coverage?” But THAT would be pushy.

Instead, the focus is on Chris’ big discount, not on Geico’s product. They told Chris how he wins, and that made things interesting for him.

Think about the products and services you might upsell your customers on, and then think about how those products help them win. Hint: nobody cares about your product. They care about their problems. Showing them how you can solve those problems is the key to upselling successfully.

Now, Go Forth and Upsell

If you’ve been hurt by years of terrible upsells, then it’s understandable that you might be hesitant to try and use them yourself.

But hopefully this post has showed you that upsells can be honest, honorable and valuable in growing your business, and they don’t have to be pushy or sleazy.

The key to a successful upsell that makes your customer happy lies in your timing and your approach. Get those two right, and you’ll be on your way to turning existing customers into raving fans.

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About the Author

Len Markidan heads up marketing at Groove. He’s focused on helping startups and small businesses build better relationships with their customers.

Read his latest posts or follow him on Twitter

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