I would consider the following:
- create 2 call queues.
- boss1 is member of call queue1
- boss2 is member of call queue2

When the 2 bosses want to speak to each other they will dial the call queue instead of the user ext.

- can also decide whether to leave the call queues visible in the directory or unpublish them (if you unpublish them, the bosses will have to memorize the extensions of the queue, which is easy enough, and other staff won’t have visibility of the queues)

You can probably use 2VideoPro extensions to the same effect. 
- Create a VideoPro user ext.
- click on it > Phone > Call rules & voicemail > Incoming calls > add number or coworker > add boss1
- do same for boss2.

When the 2 bosses want to speak to each other they would dial the VideoPro ext instead of the Licensed user ext.
 

Fantastic response, @Problem Solver  Keep up the great work - we need more members like you in our community!

@AmyLA1801 , if the solution was helpful, please consider marking it as the Best Answer.

Thank you @Problem Solver - I will research both of your suggestions and figure out which works best for our team. Appreciate the help!

Thanks for your help @Problem Solver !

The call queue solution didn’t work for us because every call my boss gets is routed to me first. We couldn’t figure out how to adjust that setting for internal vs external calls. So then we set up new VideoPro extensions and those worked!! Yes, we have to memorize more extension numbers now, but by adding them to the company contacts and assigning them extensions that are similar to their main number, it’s very easy for everyone to find them. Problem solved!

Glad to hear this!