Honestly when I had my phone call, the dean did most of the talking and carried me through an entire chronological order of the application process, from MCAT to interview, pinpointing my strengths and weaknesses and what I should make sure I address in the upcoming cycle. Luckily I had already started on most of those things or else I'd be screwed for the now June 10th AMCAS opening date. Your questions should, I would assume, flatter the dean and their school by asking how you can get better for them specifically, and the dean will actually, in general, likely address you as an applicant in general to improve you as a whole from a national perspective so that you don't just have more success at their school. So to sum it up, it likely won't be awkward silence mixed with questions, at least I hope not. The dean I talked with for 30 hit on things for me. But, if you get the chance to ask a lot of questions due to an awkward open style discussion, just think about every aspect of applying to medical school and what they think about it, how their school thinks about it, and how you fit in. I'm assuming you are a reapplicant... If not, it is probably going to be less awesome of an interview because you won't be much worth discussing yet, and it will be superficial crap you could have found on the internet. And if it is the latter scenario, just be really awesome and make a good impression and know a good amount about the school before you start talking because it is an opportunity to either help or hurt your chances. You screw up with a dean, and you'll get blacklisted and never get an interview.