This is what separates the User Interface men from the User Interface boys: the suggestion “Instead, leave the menu item enabled. If there’s some reason you can’t complete the action, the menu item can display a message telling the user why” is the most Gawd-aweful suggestion I’ve heard in a long time.
The correct answer, of course, is to create a tool tip which pops up over the disabled item which indicates why the item is disabled. That way we have instant feedback on what a user can do, and if the user is puzzled, he can easily discover why a particular item isn’t currently selected.
In Java, you can do this by calling JMenuItem.setToolTipText(); set the value to an explanation why the menu item has been disabled, and the explanation will pop up when the user hovers over the disabled item.
On the Macintosh, with Cocoa you can do this by setting the ToolTip text field in the IB .xib file with the text describing the item; call NSMenuItem’s setToolTip: method in order to update the text for the disabled menu item.
And even Windows has the ability to create tool tips for disabled menu items, though it takes a hair more work: by watching for WM_MENUSELECT notifications you can then pop up a CToolTipCtrl, or update a status bar text line, showing the appropriate text if the item is disabled.
So as much as I appreciate Joel’s comments on the software development industry, on this particular item, ummmmm… No. I agree more with John Gruber: you’re much better assuming your users are clever. But if your menu command structure contains commands which are just odd or hard to puzzle out at first glance, tool tips are much better than an idiot modal dialog box. It’s just more elegant.