The intentions of your friend are genuine. Certainly, he SHOULD be able to call in and get to talk candidly to another "annointed" one, and a member of the GB without any fear of repercussion for his questions. One of his fellow "rulers". Will it happen? No, not a chance. Despite what anyone in WT will have you believe, there is in fact a huge clergy/laity distinction. He is NOT one of the elite, the glorious, the privileged.
But all of us here know that. Your friend may not realize it quite yet, but being annointed, or a partaker of emblems, means little. In fact, it probably puts him at an even greater disadvantage at having the chance to speak to any of the "chosen ones". Anyone at the switchboard, or reception, or even the service desk, will instantly brand him as a kook, and mentally instable.
Sadly (?) for him, this will be a wake up call for sure. His heart will be crushed, and then he will begin to awaken.
To answer your original question..Yes, I would call, or email, or write, if I thought for a minute that I could speak to a fellow heavenly ruler. Now, not so much..