The most important time to keep things simple is when the user is on edge, when they will be most open to frustration. Design for over-communication and obviousness–hold the user’s hand.
One such time might be when you’re uninstalling some software, like I did recently with MailTags. I didn’t have a particular problem with the software. The trial had expired and I decided I didn’t want to register it. Here is the uninstall screen (I added the blue ovals):
Everything about the uninstall window points me in the direction of where I want to go. But to move forward, I am forced to click an “install” button. That’s the opposite of what I want. I’m an advanced user and that made me look at it two or three times. Imagine if I was a novice, or I was angry with the software.
There are also moments where your software may have to deliver bad news. Ikea’s stock availability often has to do just that. Unfortunately, there is a sea of text to wade through to finally get my answer, as you can see below (again, I added the blue oval):
These are fairly tame examples. What about when there are major errors, or the user enters an invalid email address? One of my favorite books, Defensive Design, discusses the topic in-depth. I’ve probably read it through four times and I’m still learning things.
And that’s the dirty little secret about hand-holding. Like everything else, it takes practice to get it right.