[zachware]

Depends. Not with mission critical processes like checkout IMHO. What this piece points to is a flaw in design processes. As designers and developers we see things through a logical lens of our own making.

What we don't realize is that the real world and other factors influence our target users. It's the mark of a good designer when he/she pushes user testing to understand what people will do with what we build.

In this specific case, we all know you use the magnetic pin but not everyone does. It's hard to believe but the sometimes don't.

[untamedmedley]

I agree that if your site metrics show large numbers of people set to buy but abandoning their purchase because the checkout process is confusing, then you should work to make it more user friendly.

But what I'm saying is every designer should be asking 1. How many people are having this unique difficulty and 2. Is it worth the time and COST to fix it? Moreover, will adding the information/steps to needed to clarify the process bore/put off the majority of customers who already know how to use this (for example, a tutorial that either adds an additional step or doesn't allow users to bypass it)?

A good designer should be able to plan for contingencies, but a good businessperson should be able to draw the line between pleasing a customer and watching their bottom line.