Last week I broke down why Grammarly's upgrade trigger is one of the best I've seen — embedded in your work, showing the improved result, ridiculously low price. If you missed it, go read that first. This week is part two: what happens after you click "Unlock for $0.99."
And honestly, this one surprised me.
Because when I reviewed the flow a week later with a cold expert eye, I thought it was pretty good. But this is not how I felt at the moment. Let’s dive in and see which reaction was right.
The Find
Last week's trigger was a pop-up inside your document that previews how your text improves with Pro, plus a $0.99 trial offer. I clicked.
Here's what I landed on. And look — there's a lot of objectively good stuff here. Trust signals from Atlassian, Zoom, Databricks. A "Most popular" badge on Pro. Savings percentages on annual and quarterly plans. A clear trial timeline that tells you when you'll get a reminder and when billing starts. Even the $0.99 is repeated everywhere so you know what today's charge is.
When I sat down to analyze this a week later (calm, no task in progress, looking at screenshots) I genuinely thought: this is a solid flow. Good design. Clear information.
But here's where the expert review becomes a trap.
Because I wasn't calm when I clicked.
I was in the middle of writing something. I saw my text get better. I wanted to pay $0.99 and get back to work. And instead I got this ☝️
Three plans: Basic (the one I already have, so why am I looking at it), Pro, and Enterprise (which takes up a third of the screen and does nothing for me as an individual user). Corporate logos that I can’t relate to because, again, I’m an individual user. I pick Pro, because… well, this is actually the only option for me.
This is what I saw next:
Now I'm choosing billing frequency. Another decision. Each with its own price, its own savings badge. I pick monthly.
Then the payment form. Four screens deep. At least four new decisions after I'd already said yes! By the second screen I honestly just wanted to get back to my document. I'd have happily paid the $0.99 already if they'd let me.
How many screens sit between your user's "yes" and their payment?
Why these mistakes make users ghost
George Loewenstein calls this the hot-cold empathy gap. When you're in a calm cognitive state, you systematically fail to predict how you'd behave in an emotional one. The reverse is true too. And critically, you can't design for emotional urgency while reviewing screenshots in a calm meeting room.
That's exactly what happened here. Someone designed this flow rationally: show all plans, add trust signals, highlight savings, give billing options. Every individual element makes sense. A conversion designer would approve this page.
But the sequence kills it. Grammarly's trigger puts you in a hot state: mid-task, you just saw your writing improve, the price is a no-brainer. Every condition for conversion is already met. Then the flow dumps you into an experience built for someone comparison shopping on a Saturday afternoon.
Iyengar and Lepper's jam study showed that people presented with 24 options were 10 times less likely to buy than those who saw 6. Grammarly's page isn't 24 jams. But it introduces decisions the trigger had already resolved. The trigger said $0.99. The page says "well, actually — annual, quarterly, or monthly?" That's reopening a closed decision. Every reopened decision is a moment where the user thinks "I'll come back to this later." Which means never.
The Playbook
When to keep it in mind:
Any time you ask users to pay for anything. Any product where the upgrade trigger catches users mid-task. Writing tools, design tools, dashboards — anything where the user is doing something when they hit the wall. The hotter the state at the trigger, the shorter the path to payment needs to be.
How to use it:
1. Match the checkout to the trigger, not to the pricing page.
If your trigger catches someone mid-flow with a specific offer, the next screen should be a card form with that offer pre-loaded. Not a pricing page. The trigger already did the selling. A small toggle at the top "Want a different plan?" handles the edge case without making it the default experience. Pre-select everything the trigger already told them.
2. Audit for reopened decisions.
Go through your post-trigger flow and ask: which of these choices did the trigger already answer? The price? The plan? The billing cycle? If the trigger said "$0.99 for Pro" and the next page asks "which plan?" — you just reopened a settled question. Every reopened decision cools the user down. Remove it or pre-fill it.
3. Separate your hot path from your cold path.
The trust signals, the plan comparison, the savings breakdowns, those are great. For cold-entry users coming from an email, your website nav, a Google search. They need to be sold. Your hot-entry users, the ones clicking a trigger mid-task, don't. Two entry points, two experiences. Don't route someone who already said yes through the pitch again.
Here’s a high-level idea of how it could look 👇
When it backfires:
If your trigger is vague, "Upgrade to Pro" with no price, no preview, no specifics, the user arrives cold even if they clicked mid-task. They need the comparison page because the trigger didn't resolve anything. This only works when the trigger itself is strong enough to close the sale. Grammarly's trigger is. Most aren't.
If you forget everything, remember this:
Your checkout was designed for review. But your users have work to do. Shorten the path; they have a bigger fish to fry.
🎉 Woow, you finished the issue, that’s awesome!
Hi, I’m Anastasia Kudrow, and I write Ghosted.
I am also a product growth consultant. I help SaaS teams apply psychology and PLG to build growth they can actually control. I run my own project, Growing Pains, and also work with one of the leading PLG consulting agencies, ProductLed, led by Wes Bush.
Feel free to follow me on LinkedIn:
Or check out my website, maybe we can work together: https://www.growingpains.consulting/
See you next week!