Many problems with Salesforce for Outlook (SFO) plug-in can be resolved with a clean uninstall and re-install of the application's software.
Install SFO
If SFO is already installed on your device, please skip to Step 8.
Go to Your Name | Setup | Personal Setup | Desktop Integrations | Salesforce for Outlook
Click Download
Click SAVE
After Completed...
...Close or minimize Internet browser window - so you are looking at your desktop
and RIGHTclick it.
Step 8: Choose Run ss Administrator
Step 9: Walk Through Installation Wizard
Step 10: Accept Terms
Step 11: Choose Installation Location & Install
Step 12: Installation Complete
Right-Click on SFO Icon
Choose Properties
Compatibility Tab
Click on the “Compatibility” tab
Check the box for “Run this program as an administrator” and click on ok
Double-Click on SFO Icon
Start Microsoft Outlook
Now you need to configure the “SALESFORCE FOR OUTLOOK” by right clicking the system tray icon and clicking on “Settings” and type in your username and password and select your sync folders.
After you finish the configuration the Sync process will automatically starts
Default Configuration Settings
For additional details See Force.com's: Creating Salesforce for Outlook Configurations