5 tips for upselling without upsetting


A well-delivered upsell or cross sell should delight, not deter. Here are five tips for recommendations that hit the sweet spot.

At a glance

5 tips for upselling without upsetting

  • Do you feel like you’re selling or recommending? This is a good test of whether what you’re suggesting is relevant to the customer.
  • Keep your recommendations transparent and considered.
  • Before pitching a product, check that it’s available right away.

At its best, upselling or cross selling is a win for the customer and the business. The business gets a good sale and the customer gets a product or service they’re happy with and might not have otherwise been aware of.  

At its worst, however, it can come across as pushy or greedy, alienating customers.  

Most of us have had an experience of both.  

Remember the delight of being introduced to a product that perfectly aligned with your needs? You probably think of that as the time a sales assistant ‘recommended’ a product to you – not as a time they upsold to you. That ‘you get me!’ moment when a sales rep understands exactly what you’re after before you know it yourself is a strong driver of loyalty with a brand or store. 

Now recall your worst experience. The pushy salesperson who wouldn’t take your polite “no thanks” for an answer. If you were lucky, you escaped with nothing but your frustration. If you were unlucky, you ended up spending too much money on a product you didn’t like or need. Chances of you returning to that store or brand? Slim at best.  

So, how do you recommend additional products and services that delight, rather than upselling and alienating?   

Make it relevant, not random

Every upselling strategy should be informed by your knowledge of the customer. Knowing what drives them, why they are likely to be buying from your business, what problems they want to solve, what their budget is, what they’ve bought before and what they’ve shown interest in previously all can be essential to a successful upselling strategy.   

And it should be exactly that: a strategy, not an ad hoc approach.  

Random suggestions, whether they’re offered on the shop floor by a salesperson or appear in rows and rows of unrelated recommendations on an online site, don’t just indicate you don’t know your customer, they make it feel like you don’t care about your customer.  

So instead of diving headlong into a pitch, listen to what your customer is telling you, ask a few thoughtful questions, and only then make a decision about whether a product recommendation is appropriate. 

It may be if you can match an offer to their need and show them something that could add value to their life. Whether it’s via a conversation on the shop floor or savvy data analysis to create a personalised digital experience, making your upsell or cross sell offer relevant will be fundamental to its success. 

Choose your moment – and know when to hold back

Sometimes getting to know the customer a bit more, then offering a more informed recommendation the next time they visit is a better bet. Think of it as reading the room but with data, not just instinct.  

And sometimes, knowing your customer means understanding that upselling and cross selling may not be the right approach. 

Owner of the Lemon Tree Lane gift store, Mary Jane Bailey, for example, explicitly trains her staff not to upsell.

“We are in a community-based shopping centre, surrounded by five large retirement villages and have many repeat customers because they know we treat them well and charge a fair price,” she explains. “I’ll talk a customer out of a sale or tell them where else to go rather than try to convince them to buy something unsuitable.” 

Sharing Mary Jane’s principles means knowing your customer, and nurturing their needs and preferences.  

“Our process is one of listening to the customer and getting an idea of what they are looking for, and then using great product knowledge so we can make an appropriate suggestion.”   

 Don’t be pushy

No one likes to be manipulated, either in a store or online. And with upselling already suffering from a reputation for being pushy, it’s especially important to keep your recommendations transparent and considered. Here are some tips you might want to consider:  

  • Ditch the over-the-top claims – clearly explain what value the product or service offers. 
  • Don’t ambush your customers with hidden costs. Be open about the extra dollars involved and what they will buy. 
  • If you’re using data and tracking tools to inform your recommendations, be transparent about how your business protects customer privacy. 
  • Keep customer reviews or testimonials authentic.  

Make it easy

An upsell or cross sell where the product isn’t in stock? A recommendation in the online store that’s currently sold out? Don’t make your customers jump through hoops. If you’ve successfully pitched them a product, make sure it’s available right away.  

Get creative

A good recommendation doesn’t necessarily follow the “do you want fries with that” model. Other ways to potentially facilitate an upsell could include: 

  • Posting or displaying recommendations from experts (think chefs, sportspeople, authors), other customers or even staff. 
  • Reward loyalty with gifts or discounts – it can be easier to sell to an existing customer than to a new customer. 
  • Try bundling relevant products à la Amazon’s ‘frequently bought together’ approach. 
  • Offer a free trial on a complementary product to facilitate an upsell when the time is right. 
  • Offer a discounted upgrade – think hotel rooms, cinema or fun park tickets – but be strategic about who the discount is offered to and the size of the discount to consider whether it’s creating more work for less return. 

Speak with one of our small business lending specialists about how a Prospa Small Business Loan could help take your business to the next level.

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