The $5 Coffee That Turned Into $30 (and Why I Didn’t Regret a Cent)

Jan 21, 2026

I walked into my favourite local café last week promising myself it would be a simple visit.

A quick coffee, nothing extra, in and out.

(You already know where this is going).

I used to carry my pink Frank Green cup everywhere, but after I misplaced it, I reverted back to takeaway cups. My barista, who somehow remembers my order, my cup and my mood, immediately noticed.

“The pink cup’s missing” he said, smiling.

I told him the tragic tale of the lost cup.

He nodded and replied, almost casually,

“We’ve just had a new batch of Frank Green cups arrive, same colour as yours. If you grab one, your coffee’s free today.”

Before my brain had fully processed the sentence, my mouth said, “Of course.”

Then came the kicker:

“The almond croissant has just come out of the oven… you should try it.”

Five minutes later, I walked out holding:

- a coffee
- an almond croissant
- a very shiny new cup

My “quick coffee” became a $30 purchase.

And I didn’t feel manipulated, I felt looked after.

Why This Worked (and Why It Works Online Too)

What my barista did instinctively is something most businesses try to manufacture and often unsuccessfully: he upsold

But his upsell wasn’t pushy or scripted, it was built on three behavioural principles:

1. Relevance increases acceptance

Behavioural economists refer to this as choice congruence: we are far more open to additional purchases when they clearly align with the original intention.

I wanted coffee.
A cup designed for coffee made sense.
A fresh croissant heightened the experience.

A Nielsen study found that 49% of customers make unplanned purchases when they feel the recommendation enhances their original decision.

The key is alignment, not pressure.

2. Timing matters more than persuasion

The offer came after he acknowledged something personal: my missing pink cup.

McKinsey’s 2023 Personalisation Report showed that customers are 76% more likely to consider brands that recognise their individual context.

He didn’t just sell me a cup, he solved a micro-frustration I’d already told myself a story about.

3. Humans respond to “service-based selling,” not sales-based selling

Research from the Journal of Retailing shows that when a recommendation feels like service rather than sales, customers perceive it as supportive rather than transactional.

This increases satisfaction and repeat behaviour.

That’s exactly how it felt!

The Professional Lesson

Great upselling has nothing to do with pushing for a higher order value and everything to do with creating a smoother, more supportive experience for the person in front of you.

When it’s done with intention, people feel that you’ve understood what they truly need, their decision-making becomes more natural, and the relationship between you and your customer grows in a way that feels steady and respectful.

Think for a moment about the experience of someone choosing a print as a gift.

They’ve already imagined the person who will receive it, chosen the image, and committed to making it special. When you then offer a frame that complements the print or gift wrapping that saves them time and adds care to the gesture, you are not “adding extra items”, you’re anticipating what will make their gift feel complete.

You’re meeting them halfway, at the exact moment when the next step feels obvious and helpful.

So here’s a reflection for the week: consider where in your business you could recognise a need a little earlier, reduce an unnecessary point of friction, or create a sense of completeness that your customers would deeply appreciate.

Want help identifying the opportunities in your own customer journey?

That’s the work we do inside Conversion Magic, seeing what your audience sees, and helping them choose you with ease.