I want to Shuffle my Nano!

I have a shuffle. When I hook it up to the computer I have a section at the bottom of my screen which allows me to "auto fill" from my library or play list of my choice and the option to replace all existing songs on the shuffle. I want to be able to do this for my wife's newly bought Nano, but the same section at the bottom of the screen does not appear. Does anyone know how?
Cheers.

Thanks for your responses. I have managed to do what I want, in a round about and painful way. All of the songs that my wife wants I have numbered 1, 2, 3, 4 or 5 in the "comments" section of each song (some 1,300+). I have then created 5 smart play lists, each one limited to all songs with a number 1 - 5 in the comments box. So, when she gets sick of "smart play list 1", I simply wipe all the songs and upload "Smart play list 2" and so on. If she suddenly wants all of "ABBA" (yeah... I know!), instead of a few songs from it, she just has to let me know and I can wipe something else in order to fit all of the ABBA songs on. It's done now and suits me (her) fine, but if someone has a better solution, please let me know.
It would be much easier to have the same function as the "ishuffle", which would allow auto updating at random from the library or play list of my choice. I assumed that all of the ipods and itunes syncing would be the same. If I had of known this not to be the case, I probably would have gotten her the 60GB one and be done with it... But we live and learn.
Perhaps someone at apple/itunes could allow the ishuffle technique of filling ipods at some stage in the future.
Cheers!

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