How to hear audio output and input from calls using remote control?

Our work requires one specific feature that involves me as the one doing the remote control over my coworker's laptop while he's the one that will take calls and talk as I navigate his laptop and take notes for him.

Here is our challenge, I can see my coworker's screen and different apps, but can not hear the conversations that he's having through the call whenever he's connected to a headset. However, if my coworker takes off the headset I am able to listen in.

In simple terms, I am able to remotely control my coworker's desktop and I can hear the conversation from the call if it is on speaker, but whenever he's connected to a headset I cannot hear any audio input and output from the phone conversation that he has with clients, and this does not allow for the clear client experience with the quality that we need. Does your service allow this, and if we need to trouble shoot this, how easy is it to get support? Our needs are pretty basic, but this one aspect is very important to us.