Understanding the Psychology of Upselling
Most people tend to think of upselling as some sort of pushy, fast-talking salesperson tactic. I Think like itâs all about wringing the most cash out of a customer. But thereâs 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 theyâll 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 â 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 â 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 theyâre almost too available and too heavily discounted. Thereâs nothing urgent or special about them at all.
Itâs like: âHere are some socks to go with those shoes, why not. â That is no way to increase your order value.
Customers see through it instantly, especially when the upsell doesnât match the main item theyâre 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 donât 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 thereâs a fine line between exclusive and manipulative - sometimes, itâs 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 âonce in a lifetimeâ deals in a way customers can understand easily. This also isnât about pressuring people or driving up revenue for revenueâs 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.
Itâs a skill to know when the timing is right - itâs a rhythm, an art. Itâs 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.
Itâs important to strike while theyâre hot. Theyâre engaged - theyâve been interacting with your product and have made the decision to buy. They are buying from you because youâve 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 doesnât really care about your feelings or what you want in life - just that they want your body and your money in exchange for their âservicesâ.
Itâs 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. âHey if you forgot to add something on or would like to add something extra, now is your chanceâ. This makes people feel like their choices are respected, and that this isnât 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 theyâre ready. Sure, everyone says you need a âCRMâ or a fancy loyalty platform, but often these are kind of hastily bolted on and left running â like an ignored treadmill after New Yearâs.
If the data isnât clean, itâs 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. Weâre working from a web of preferences, habits, and sometimes randomness â 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 â 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), thereâs groundwork needed before automation helps anyone at all.
When we use our data to give people helpful pointers about things theyâd enjoy or benefit from, with timing that feels convenient instead of intrusive. Thatâs when the magic happens. Itâs always worth remembering that customers donât actually care how clever our personalisation engine is â theyâll 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 itâs 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. Itâs 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 youâre 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 donât really care for gifts and discounts but want more flexibility with delivery windows - or theyâre people who hate entering card details manually and would appreciate an autofill option more than anything else. It isnât always straightforward to figure out what your audience wants - but then thatâs 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 itâs all about the dollars on a spreadsheet. They get fixated on revenue and fancy numbers, convinced thatâs the only worthwhile measure of progress. While you do need to keep an eye on dollars and cents, it doesnât even begin to tell you the whole story.
You donât want to come across as a money-mad retailer. If youâre pushy with your upsells and pressured into purchasing something, it comes across as greedy. Especially if youâre not transparent about what youâre 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, itâs 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. Itâs not really a black-and-white metric.
If anything, itâs 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 isnât always straightforward.
Especially as a business owner who needs to look at how many sales youâre 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.