I think they're signing him to fight GSP. GSP wants to fight, but only the "right" opponent. GSP would fight Conor, but I don't think Conor wants that fight (especially now) because it would be more of the same from the last fight. GSP was trying to lose weight to get down to 155, but I really don't think the UFC wants him to fight Khabib, because there is the risk of him winning and leaving the division/semi-retiring again like he did in his last fight.
I think they give Askren a winnable fight first to build up his hype a bit on a big card and then he fights Georges early to mid next year. I also think they try Khabib-Tony F again. And I imagine Conor either fights Nate 3 or just waits for a different opportunity to develop.
BTW, Askren and Woodley wrestled together at Mizzou and they have sparred together a lot at Roufus, and from what I understand, Askren always beats him - like a big bro/little bro relationship. Now, that's just sparring, but I also heard the same things about TJ and Cody - TJ has always been the "big bro"/mentor in the gym. It's hard to overcome that psychological edge.