I have Windows 7 and use click to call. Once you install Click to Call make sure you set the correct information within it, username password, call manager ip address etc. The in outlook you should turn on smart tags. Tools, options, Mail Format, Editor Options, click on Proofing, then AutoCorrect Options the click the Smart Tags tab. Now select the label text with smart tags option then select the Telephone Number (Smart tag lists). There may also be a Cisco Smart Tag in there if so select that one too.
Now when you go into your contacts in Outlook or you are on a webpage or any microsoft office application you can highlight the number then right click, then go to additional actions and there you can make calls multiple ways. If you right click on a contacts name it will show all the numbers associated with that particular contact with different ways to call them too under the additional actions area.
