If you see that contacts in Outlook are not being synced with your Blackberry you can first ensure that wireless sync is enabled. If it is you may need to reset and reload your contacts.
To do this go into contacts and press the Blackberry button and select options. Type RSET (nothing appears as you type) from the options menu and when you have typed RSET in it will prompt if you want to erase contacts and reload from server. Select yes and wait a short while for the contacts to be populated.