John was using Microsoft's built in voice recognition to dictate in Word. He uses the Logitech G35 USB headset and it learned his voice fast. But it won't work at all with chat windows like Skype, or others. It just won't function at all. Leo says that some applications don't support it dictation. Leo suggests doing a test call on Skype to be sure he's getting a good connection. If he has a good connection and dictation still doesn't work in Skype chat, it may not be supported.
Leo also recommends going to dictation.io through Google Chrome. It's a very accurate voice dictation plugin for Google. He can always cut and paste, too. Dragon Dictate works in Firefox, but not Explorer. So it could be a browser support issue.