For bonus points, take five or ten seconds to explain to the customer how multiple windows can exist at the same time, and show how the Windows taskbar has a button for each of them.
This stresses one observation I've made several times when seeing Windows users work with computers: Despite its name, Windows is the most un-windowy of windowing environments – Enjoy the irony. The way it and its applications work encourages full-screen windows – and for many people that seems to be all they know about. Even when using other computers they go straight for the 'maximise' button and will be irritated if the window doesn't occupy all of the screen afterwards.
Another very true point is the following:
The underlying design flaw here is the existence of Webmail, trying to put a usable e-mail interface inside a Web browser window.
I couldn't agree more. In fact, I tried writing a piece on why webmail sucks a while ago with a good bit of Hotmail bashing in it. I wrote it because many of my friends gave me webmail, in particular, Hotmail addresses and it were always those people who were hard to contact, had expired addresses, spent a lot of time checking all of their accounts, because they couldn't forward etc.
I still think that webmail has its merits as you can use it from about everywhere – though the ability to ssh home to your efficient copy of pine is probably as ubiquitious. I am sure that webmail will beat Matthew's for suggestion for a hypothetical alternative interface which
would need to be implemented, and be extremely popular, on MS Windows, GNU/Linux, and Mac OS X — so that someone going in to any random Internet cafe could reasonably expect it to be present.
This kind of approach, if it existed, will either give us applications that share some common protocols or interfaces, say to retrieve mail settings from some central database, but may look and feel differently on various platforms. That wouldn't be good as one of the advantages of webmail seems to be that it offers the same looks wherever you are (modulo design changes or 're-branding' which are bound to cause confusion in users). The alternative would be some Java application that looks the same everywhere. But having used Java applications before, this doesn't sound too promising either.
Yeah, there is a problem.