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Assuming you are using the Embedded Voicemail... Dial the Voicemail access code (same number you dial from your phone). When prompted to enter the other phone's password, dial *. You will be prompted to enter your mailbox number, followed by your passcode.
There are a number of Headset that will plug directy into the back of your 5212 phone. (I would suggest Googling for results) As for Monitoring an agent the MitelICP has the capability to allow a supervisor to dial a code and mointor the agent while on a call. Contact you Mitel Vendor and I'm sure they would be happy to make the program chage for you. (This is a class of service and Feature acces code change)
No you cannot.
The Mitel 5212 uses propitiatory software unlike SKYPE which uses open architecture software.You IS Dept. could invest into a Teleworker Server and you could have all of the features of your office phone at home.