I know exactly what you are trying to do... Unfortunately, I have been trying to do the same thing. As of right now, because we cannot cable "sync", I am unaware of anyway to move contacts from outlook to Blackberry...My hope is that some web based service will be made available, which will allow me to upload my contacts, however, nothing free yet.
Because we are wireless, and we are using Outlook Connector, the only way would be to have a "wired" hack, which would allow us to download an outlook database. I have not seen this, probably because the Outlook Connector is not very prevalent.
I have seen import utilities, which will convert outlook to Lotus, but not very successfully
.. Plus, you use valuable space up on the server..
let me know if you find something different.