Danny Sullivan hosts an almost daily radio show/podcast at WebmasterRadio.FM named The Daily SearchCast, as far as I know, this show is listened to by many top SEOs and SEMs daily, I personally try to listen to ever episode. This coming Tuesday, May 16th at 11:30AM (EST), Danny will be at the GooglePlex, in Matt Cutts's office, asking Matt questions, live on The Daily Search Cast.
Both Danny and Matt have more details on their blogs about the event.
Currently Danny is requesting the submission of questions to ask Matt during the show. Currently on Danny's list are;
(1) Issues with missing pages some are reporting & the Google's "out of space" concerns (2) Dealing with domain names (see Does Google Use Whois Information?, Google Effect Of Domain Name Expiration & Change Of Ownership) (3) Sitemaps and spam checking tools (see Google Sitemaps Adds Spam Checking, New Webmaster Help Center & Other Features)
Number two should be very interesting, so clear your schedule and jump on the feed. More details on how to listen over here.
Do you want to submit questions, visit the Search Engine Watch Forum discussion thread and submit your question(s).