For a windows image you have to install the VMware tools to shrink the disk.
VMware guide
http://www.vmware.com/support/ws5/doc/ws_disk_shrink.html
The VMware Tools are installed by: Start your virtual Operating system -> Move mouse to the top of the screen and select 'Virtual Machine' -> 'Install VMware Tools'
VMware Tools location
C:\Program Files\VMware\VMware Tools\VMwareControlPanel
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