Understanding the Psychology of Upselling
Most people tend to think of upselling as some sort of pushy, fast-talking salesperson tactic. I Think like it’s all about wringing the most cash out of a customer. But there’s more subtlety to persuading someone to increase their order value than just whacking a bunch of extra add-ons at the point of purchase and hoping they’ll bite. It's about understanding what's making them tick right now, why they are hardly ever here, and what they want - even if they're not entirely aware of it themselves yet.
This is hardly ever pretty nuanced. I mean, it's really a lesson in psychology - leaning into what motivates your customer intrinsically rather than what you can dangle in front of them that might look shiny or attractive but that they don't actually need or even want. Now, this isn't something that's going to come easily on your first rodeo but looking at how your customer goes about navigating your website (with analytical tools like heat maps), or comparing baskets before and after they've checked out will help you notice patterns and better understand their behaviour.
But it's also important to realise that upselling can never be an exact science. You might have an inkling about why someone's come to shop with you based on various cues (their past shopping habits, wish list items, abandoned cart history), but there's still plenty you don't know. And this is important.
More or less. Because when you don't know enough, you're far less likely to fill in the gaps with absolute rubbish – instead you're more likely to make meaningful suggestions based on real data. It seems like ultimately though, this is all about connecting with your buyer based on a shared understanding and trust (of what they're looking for and how you're trying to fill those needs) at a certain price point (something you'll both have explored before buying). This is also why fostering loyalty becomes so important for any brand who wishes to retain customers – by using incentives like discounts or freebies for existing customers, repeat purchases become more common (without being perceived as forceful).
Crafting Irresistible Offers
Many brands treat upsell offers like a warehouse clearance sale. I Doubt they’re almost too available and too heavily discounted. There’s nothing urgent or special about them at all.
It’s like: “Here are some socks to go with those shoes, why not. ” That is no way to increase your order value.
Customers see through it instantly, especially when the upsell doesn’t match the main item they’re buying. Irresistible offers are nearly always crafted on some fairly foundational truths: people want something worth their time and money, most purchases are driven by emotion first and logic second, and customers want to feel seen by the brand they support. Getting it right often means you don’t have to price slash at all.
Many businesses can up their average order value even without dropping a single dollar on their product prices. The trick is understanding what buyers need with the purchase they're making today - what experience or outcome they want - and finding ways to get them there faster. And yes, you have to be conscious of how you frame these add-on offers. Most will say that presenting an offer as an exclusive deal makes it more appealing.
But there’s a fine line between exclusive and manipulative - sometimes, it’s very blurry indeed - so language matters just as much as pricing does. I think irresistible offers tend to take two forms: add-ons to the main product that improve its utility or quality, or bundles with one strong hero item that become “once in a lifetime” deals in a way customers can understand easily. This also isn’t about pressuring people or driving up revenue for revenue’s sake either - it has to actually be good for the customer (not just for you). Otherwise it comes off as pushy, which sort of defeats the whole point of it being irresistible now, doesn't it.
Timing: When to Present Upsell Options
Most people get the timing wrong. They ask for the sale at the wrong moment - before the original buy has been made, or too late and people are rarely already at the checkout.
It’s a skill to know when the timing is right - it’s a rhythm, an art. It’s very human and as such hard to get right with automation. What you want to do is wait until your customer has committed to a sale. Sort of.
It’s important to strike while they’re hot. They’re engaged - they’ve been interacting with your product and have made the decision to buy. They are buying from you because you’ve built trust. You have created rapport.
Research shows that people are more likely to add value at this point. Where upselling fails is where it oversteps and gets too pushy, too early. More or less. It feels gross, like being hit on by a stranger who doesn’t really care about your feelings or what you want in life - just that they want your body and your money in exchange for their ‘services’.
It’s easy to see why people might leave the store - especially if they only came in for a bottle of milk. But there are other times when an upsell can work, like when a purchase has been confirmed.
Post purchase emails can be effective because they offer reassurance around flexibility. ‘Hey if you forgot to add something on or would like to add something extra, now is your chance’. This makes people feel like their choices are respected, and that this isn’t about getting more money from them but an opportunity for them to tailor their order to suit them best.
Leveraging Customer Data for Personalization
I think people get a bit starry-eyed about customer data and rush to action before they’re ready. Sure, everyone says you need a ‘CRM’ or a fancy loyalty platform, but often these are kind of hastily bolted on and left running – like an ignored treadmill after New Year’s.
If the data isn’t clean, it’s just digital detritus. More or less. As I see it, what we get wrong is either not collecting the right bits of information at all, or collecting everything and then drowning in it.
The reality is you want enough to trigger curiosity and reveal patterns that matter for upselling. A first-name greeting in an email is nice, but knowing someone always upgrades their foundation shade every two months is gold dust for a beauty retailer. We’re working from a web of preferences, habits, and sometimes randomness – if your espresso drinker suddenly orders decaf in November, should you send them both options. Or do you risk looking nosy.
It gets murky when we start talking about relevance. The best upsell experiences are when customers feel truly seen – but not watched in a creepy way that makes them want to burn their laptops. Some segments or repeat customers will appreciate suggestions based on previous picks; others will want to be surprised.
Your million-dollar customer might have one clear pattern (they upgrade every release), and another who spends five dollars a month never strays from routine. Which one do you invest time getting to know. Tricky. My take is: if your database has more duplicates than deliberate entries or every customer has the same birthday (true story), there’s groundwork needed before automation helps anyone at all.
When we use our data to give people helpful pointers about things they’d enjoy or benefit from, with timing that feels convenient instead of intrusive. That’s when the magic happens. It’s always worth remembering that customers don’t actually care how clever our personalisation engine is – they’ll reward us because we made their choices easier without making them squirm.
Creating a Seamless Checkout Experience
Most brands think of the checkout page as a money machine. That it’s where the cash flows in, so you can just throw in everything that could increase the final number on an order and call it a day. This includes things like pop-ups, questions and offers. A lot of people also overdo the discounts - they take every opportunity to offer more discounts or ask buyers to check for more discounts by submitting their email or sharing the product with friends.
But too many distractions cause overwhelm, confusion and distrust. It takes away from a clear customer journey. It’s not just about how many actions you can have on your checkout page, but how many actions a buyer would want to take. The best way to make sure you’re doing this right is to start with customer research, find out what they value at checkout and then experiment based on that feedback.
Maybe your customers are seasoned online shoppers who don’t really care for gifts and discounts but want more flexibility with delivery windows - or they’re people who hate entering card details manually and would appreciate an autofill option more than anything else. It isn’t always straightforward to figure out what your audience wants - but then that’s why you run tests and study analytics after implementing changes based on feedback. There are several ways of doing it - some brands create loyalty programs that allow customers to buy add-ons and get early access, exclusive perks, gifts etc.
, others allow buyers to buy products together for less if bought individually. The main thing is to get out of your own head and focus on what matters most - understanding your audience so you can create seamless experiences for them at checkout that keeps them coming back for more.
Measuring Success: Tracking Upsell Performance
Most people seem to think it’s all about the dollars on a spreadsheet. They get fixated on revenue and fancy numbers, convinced that’s the only worthwhile measure of progress. While you do need to keep an eye on dollars and cents, it doesn’t even begin to tell you the whole story.
You don’t want to come across as a money-mad retailer. If you’re pushy with your upsells and pressured into purchasing something, it comes across as greedy. Especially if you’re not transparent about what you’re upselling and refuse to back off when someone says no. That kind of overzealous approach can quickly leave people with a bad taste in their mouths, which can hurt your sales.
In my experience, the upsell is not always about aggressively increasing your average order values (AOV). Sure, it’s nice to earn more money and drive greater profits. But it also has to be executed with sincerity and honesty for your business to realise any sort of growth.
Measuring the success of an upsell goes beyond just tracking whether a customer took you up on their offer or not. It’s not really a black-and-white metric.
If anything, it’s more about whether they want to stick around after their purchase or come back for future ones because they believe in your brand and its offerings. An important consideration here is how the customers feel about the overall experience - whether they were satisfied with what they received as part of their purchased upsell or if they felt like they made the right decision investing in your product or service in the first place. The way I see it, the reality is seemingly that putting your customer first isn’t always straightforward.
Especially as a business owner who needs to look at how many sales you’re closing at any given time. But this customer-focused way of approaching an upselling campaign can supposedly work very well for businesses if leveraged correctly over time.
Measuring how satisfied someone is sometimes by regularly soliciting feedback can be an interesting gauge of success too. This can be done with surveys, reviews and testimonials that allow potential customers to learn more about your business offerings from existing ones, hopefully influencing them positively in favour of giving your brand a chance in future.