(In which I, Rob S., a man of relative experience with the personal computer, failed to install a program.)

It begins with a desire to communicate.

As I had recently re-imaged my machine at the office, I realized I was yet to install Windows Messenger.  A quick trip over to MSN and I’m ready to roll.

The process begins with this dialog, which is also where it ends.

Confronted with a confusing array of check boxes, progress bars, buttons and links, I simply froze.  This was unlike any installer I’ve ever seen, and I’ve used every computer from the Atari 800XL, Apple IIe, various PCs and Macs for 20+ years.

I sat there, perplexed, until the top half of the dialog sprang to life and changed to this:

The installation had already begun and subsequently failed, all before I could understand what I was looking at.  I clicked the “Get help with this” links but they presented me with the software installer equivalent of a brick wall – a general help page at the Messenger site.

Having failed the installation with no idea what to do next, my only remaining course of action was to quit the installer, so I did.  This web page appeared:

As some sort of cruel parting gift, Microsoft drops me at the Sign In page.  Or is it the Sign Up page (see top left)?  Where I would have loved to sign in with my new Messenger ID had Messenger finished installing.

Let’s look at went could have gone better:

• The installer dialog, in and of itself, is far from the most complicated dialog out there.  In context however, it is amazingly complex.  When an installer appears, I expect to repeatedly click “Next” until either (1) the installation completes or (2) the installer tells me to close Firefox and Microsoft Office.
• The word “waiting” adjacent the Messenger and Sign-In Assistant components should be relabeled “installing.”  Just a few pixels above, the dialog refers to its own action as “You’re installing these programs.”  Why the confusing terminology?  Who or what is the installer waiting for?
• “As each item finishes, you can start using it while the others install” – I would just be happy to get something installed, let alone begin using my installed programs while the others are being installed.  In my entire history of using computers, I’ve never met an installer that’s allowed me to begin using parts of the applications it was installing…

…which brings us back to the title of this post.

While the installer allows you to continue installing and running in parallel, this new installer presents an interface and interactions completely unfamiliar to anyone who’s installed 100 other programs.

Don’t buck the trend.  Your users have already learned how to install a program – play to their strengths.