You may be familiar with Bruce Tognazzini, who is widely considered the father of the Macintosh UI. He's no longer at Apple, but he is part of the Neilsen Norman dream team. He also maintains a website with the ten most wanted UI design bugs:
- Power failure Crash
If the computer loses power for more than a few thousandths of a second, it throws everything away. - The macintosh dock
There are actually nine separate and distinct design bugs in the Dock, probably a record for a single object. You can read about them all in my Article, The Top 9 Reasons the Dock Still Sucks. - Mysteriously dimmed menu items
Designers offer no way for users to discover why a given menu or option has been dimmed (grayed out), nor how to turn it back on. - ASCII sort
15 Dec 2008 sorts as being before 2 Jan 1900 - URL naming bug
Many browsers disallow entry of spaces & other normal human-language characters into web addresses. The rest do inappropriate things with them. - Let's you save me some work
Weird formats for standardized data - The disk drive nazi
"Unauthorized" removal of floppy or hard disks is punished severely - ecommerce hostility
ecommerce sites are making it as difficult to buy products as humanly possible - "Smart" functions that aren't smart
"Smart" functions often make the wrong decisions - Focus-stealing
You're working on a multitasking system, typing away merrily in window A. Meanwhile, some background task decides it needs your attention, pops up a dialog, and moves the keyboard input focus from the window you were working on to its dialog box.
Two of these come across as cranky "I coulda done it better" complaints about specific Apple design decisions he doesn't agree with. But the rest are truly aggravating UI problems in every GUI. This is just the top ten; if you're feeling extra cranky, there are hundreds of others listed at Tog's Bug House. Similar topics are covered in his two classic books Tog on Interface and Tog on Software Design.
For a different take, try this summary of a PARC lecture by Marissa Mayer on Google's "user experience" -- which offers some interesting insight into the way Google approaches user interface design.