In general there is nothing special that should be done in order the progress area to be shown on the page.
There is a certain possibility that you are uploading file with relatively small size and it's uploaded very fast.
Please try to upload a larger file (+20mb) and let us know if you still experience the same behavior.
the Telerik team
Register for the Q2 2011 What's New Webinar Week. Mark your calendar for the week starting July 18th and book your seat for a walk through of all the exciting stuff we will ship with the new release!