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How to Upsell Better from Trials

How to get the most from Cheatsheets

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How to Upsell Better from Trials

5 mins Cheatsheet
How to Upsell Better from Trials graphic 0How to Upsell Better from Trials graphic 1How to Upsell Better from Trials graphic 2
  • 1. Trial reminders (the good, and the better)

1. Trial reminders (the good, and the better)

Whenever a service takes a payment card before a trial, I immediately have a dread of “oh, I bet I forget to cancel this in time”.

To be clear, companies ask for a card in advance, because it removes the need for the user to make a decision (if they want to stick around).

The inverse requires the user to actually bother logging in and entering a payment method—this will create churn.

One UX technique that companies use to calm some of this pre-trial anxiety is to promise that they’ll remind you a few days before your trial ends.

Canva Trial

UX Bite #301

Browse all UX Bites

The easy implementation would be a simple email automation, like Canva above.

But you can do better.

Imagine that you’re booking a flight. Which of these two scenarios would you feel more comfortable in:

Scenario A: “It's company policy: all of our seats come with overhead luggage space”

Scenario B: “Would you like to reserve overhead luggage space? [yes] [no]”

Although the outcome is identical, it can be more reassuring if there’s user input involved in the process.

i.e., you’re more likely to believe in the outcome. Surely the company is less likely to ignore a direct request, rather than a broad company policy, right?

Now look at Rise:

Peter Ramsey, Built for Mars Founder

Written by Peter Ramsey

Consultant to 100+ companies

Published: 23/01/2024
Last edited: 08/07/2026