I feel super awkward calling to find out if there is a will but if there isn't I would imagine it could take months to get sorted out.

You're going to sound awkward at first no matter what, the only way to get better is keep doing it.  

We were all awkwardly quiet, a few people were kind of chuckling at him.

once they call you pick up that phone. your first couple of conversations will be awkward as hell but its a fast learning curve that way.

Too many references are going to be made to local areas and unless you have a firm grasp on the local market this maybe awkward.

I'd love to throw my hat into the ring for this one.I've worked hard for everything I have, which makes it awkward for me to tell someone "why me", why I should be considered for such a gift.

I just hate that awkward moment.

I just don't want to be put in an awkward position or put someone else in an awkward position because of my ignorance.Thanks! 

I am not so sure that he is not talking with Lawyer T based on the awkward timing you mentioned.  

This is could be awkward because it means you have to work with them for essentially 2 months while you switch over.