Sure for Palm side, use Palm Desktop to get data into Outlook.
http://forums.palm.com/palm/board/message?board.id=windows_hotsync&thread.id=27162http://www.tomshardware.com/forum/5933-36-transfer-data-palm-outlookFor getting the Desktop Manager/ blackberry portion to work, just download DM from RIM's site for free at here:
http://na.blackberry.com/eng/services/desktop/Once installed you will need the USB cable and just hook that to the PC and bb device. Start the DM software and it will recognize the device, then configure the Desktop manager to sync with Outlook. Use this guide.
http://na.blackberry.com/eng/support/docs/subcategories/?userType=1&category=BlackBerry+Desktop+Software