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You can use the standard Windows file selection functionality. When you have the "Import File" dialog open, use the CNtl or Shift keys to select multiple files.
Colum has good advice. Also, since you're new to this, there are a few curiosities that occur that can be puzzling to newcomers. If you have graphics in your Word docs (screenshots, etc.) a new folder will automatically be created. So if the name of your Word doc is MYDOC.DOC, graphics will be placed in a new folder called MYDOC_Files.
Another "hitchhiker" to the process is the creation of a CSS file automatically created for each Word doc. After the import you have the choice to reassign any style sheet you like, regardless of the CSS originally linked.
Another tip if you're new to importing, go to Peter Grainge's excellent site.
Follow the links: RoboHelp > Importing from Word for some excellent ideas.