&gt; Probably the best thing Microsoft could have done back then was make a little pseudo-video† walkthrough, showing people what&#x27;s in the Start Menu and what happens when you click on a few of the items in there.  
They did that. Windows 95 came with a whole bunch of tutorials. IIRC they worked like you describe. There was also the notorious &quot;Tip of the day&quot; via the welcome.exe.