Looking for a Leader

We are searching for a new high school Principal and Assistant Principal, 14th year in District and going on 5th Principal and 4th AP.  I want a Leader, not just an Administrator.  I want someone that is digitally literate, as well as versed in the current books about education, a connected Educator. I want someone that is a learner, understands and utilizes current tools & trends, understands what culture of learning is, realizes there are deficiencies in our system and wants to make school different. I want those things being OBVIOUS when you talk to them and JUMPING off their resume.

How do you find that if your interview teams are not full of connected educators?
Am I overrating the idea of connected, digitally literate, PLN, etc...? 
What if none of the candidates have a digital footprint?
How many questions should you have to ask until some of those things come out?
(How many questions do you get to ask in your interview sessions?)