“Write about stupid emotions” Conversation That Tripled My Client’s Upsell Conversions
That’s what I blurted out during a coffee chat with one of my clients few months ago. She was asking how to improve upsell conversions in her program.
“Write about stupid emotions.”
That’s what I blurted out during a coffee chat with one of my clients few months ago.
She was asking how to improve upsell conversions in her program.
The actual question?
“How do I get more people to take the 3-month upgrade when they join my community?”
She had a great offer. Great content. Clear pricing.
But her upsell message wasn’t landing.
It was too “mechanical”.
So I paused. Took a sip of delicious speciality coffee from Colombia. And said:
“Honestly… you need to write about stupid emotions.”
We both laughed (and no, I don’t really think emotions are stupid).
But that was the moment the breakthrough happened.
The problem with most upsell copy (and conversations)
Most upsell messages are written like this:
“Here’s a better deal. It saves you money. Take it now before it’s gone forever.”
It’s logical. Rational. Straight to the point.
(DISCLAIMER: I’m referring to digital products, coaching services and memberships. For physicial webshop products sometimes “get more of the same for cheaper” makes perfect sense)
But here’s the issue:
There are two common paths people take with upsells and neither of them actually work long-term:
A) The overly rational route - just listing features, numbers, discounts.
B) The emotional hype route - pushing urgency, scarcity, and high dopamine so the buyer acts without thinking clearly.
Both miss the mark.
One forgets the human.
The other manipulates the moment.
What actually moves people
You want your upsell to work (without feeling like you are pushing it) ?
You have to speak to the real emotion they’re feeling - not manufacture a fake one.
When someone buys from you, they’re in an elevated state.
They just said yes to themselves.
They’re hopeful. Nervous. Energized. Vulnerable. Ready.
That’s not the time to drop hard logic...
...and it’s definitely not the time to pressure them into another decision just because they’re on a high.
It’s the moment to meet them with truth.
To honor the commitment they just made.
And to offer them a path that feels like a natural extension of what they already decided.
That’s the sweet spot.
That’s where conversation becomes connection.
Before and after - the real stats
We tested this with her actual upsell.
Before we worked together:
78 new enrollments
10 said yes to the 3-month upgrade
12.8% upsell conversion
Then we rewrote the message using real language that acknowledged where they were emotionally - but didn’t hype.
Today:
46 additional enrollments
24 additional upsells
New upsell conversion rate for the people we worked with? 52.2%.
(And yes, 50% is now a stable upsell conversion rate!)
That’s a 307% increase in conversions - just from changing the upsell popup message.
Same offer.
Same price.
Same audience.
The only thing that changed?
The way it spoke to them.
We didn’t do anything wild
We didn’t run a split-test funnel.
We didn’t overhaul her backend.
We didn’t add countdown timers or throw in urgent bonuses.
We just made the message feel like a conversation.
A human moment.
And it worked.
(Special bonus for you) The mini framework - Emotional Flow for upsells
While I’m not going to give you exact copy template, here’s the next best thing.
The structure we used (feel free to steal it and make it your own):
1. Acknowledge the moment they’re in.
→ "You just said yes to yourself. Let’s make it count."
2. Normalize the next step.
→ "Most members stay 3 months anyway - this just makes it easier."
3. Anchor the value emotionally.
→ "You’ll have time to (feel in the blanks), feel (feel in the blanks), and (feel in the blanks)"
(yess, “feel” is there on purpose, pun intended)
4. Invite instead of push.
→ "If it feels right, take the 3-month path. If not, no worries - either way, I’m glad you’re here."
The upsell turned into a soft landing, not a sharp push.
It made emotional sense, not just financial sense.
Bonus long-term insight from the data
Here’s what most people don’t realize:
Clients who initially commit for longer often:
Renew at a higher rate
Stay longer
Become your best referrers
So even a small increase in that first upsell?
It compounds. Quickly.
It’s not about squeezing more out of each client.
It’s about offering a path that helps them win longer, earlier.
Final reminder: You’re not selling an upgrade - you’re offering a better experience
And the job of your upsell message?
Not to convince.
Not to pressure.
Not to trick.
Just to offer a clear, calm, natural next step - one that honors the moment they’re in.
So next time you’re writing an upsell…
Don’t just talk about savings.
Don’t try to ride emotional hype.
Speak into the moment where they are - with care and clarity.
That’s what builds trust.
That’s what increases conversions.
And that’s what makes a client-first business actually work.
Want help designing an emotional, ethical upsell that actually fits your offer and values?
Let’s talk - or just reply and tell me what’s not converting the way you hoped.
No hype, no pressure. Just clarity.
Because sometimes, all it takes… is writing about “stupid emotions.”