Thanks for posting your question. One approach could be for the assistant to register the line that belongs to the boss so all calls would be routed to the assistant. Then the boss could have a phone that registers a different extension not shown in the system directory. Since no one but the assistant would know the number to the phone that the boss is using that may take care of the requirements. If you want to take an extra step and only allow the assistant to be able to call the boss you can utilize Find Me Follow Me (FMFM) and only include the assistant in the priority list. The Everyone list would need to route calls elsewhere.
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Here is another option that can be used. It is very similar to a work around we have for shared line on multiple phones.
Boss phone ext to public is 5004
Receptionist personal is 5005
Boss Private ext is 4004
On the receptionist phone have her personal exten of 5005 and then boss pub ext of 5004, then can have a Status Group with Boss Private ext of 4004 to monitor boss phone.
All customers and employees if desired would only know about 5004.
Only the receptionist phone will have 5004 registered.
On the boss phone you will have private ext of 4004.
If you go to IP Phone Configs, you edit the boss phone config, you can change the extension label to make it say 5004. Then click apply. This will make the Boss think her extension is actually 5004. No need to confuse the Boss! =)
Then edit the Boss user for the 4004 Extension via Voice > Stations > User Accounts. Go to User Config tab, in the Internal Called ID Number custom Entry field edit it so that is says 5004 and modify External Caller ID Number if Boss has a DID like 2569635004
Then go to the Current Settings tab and uncheck the System Directory box to make sure the Boss private extension is not listed in the directory as Matt mentioned above. Click Apply.
When configuring like this all calls to 5004 will go to receptionist, receptionist then can forward calls to the boss phone.
When the Boss places calls, boss caller-ID will show 5004 so if people hit redial the calls will go back to receptionist.
Hope that helps. Let me know if you have any questions.
I think I like this solution even better - lets the end users not have to worry with extra details. Thanks for the tip!