I've visited the last 5 years 9 conferences. SIC and ESWC.
There are a lot of speakers.
They all can speak but only few of them are able to tell you something.
When it comes to the point that you think "What the hell did I learn from this session?" then the good sessions are separated from the bad ones.
It's always a pleasure to listen to Sharon Housley (www.notepage.com) and especially to Dave Collins (www.SharewarePromotions.com). Usually they have the best sessions during a conference.
Dave is a specialist in SEO and Google Adwords.
#1. Dave Collins - Dave is incredibly knowledgeable, additionally he is very entertaining and an engaging speaker. He is always a top-rated speaker. (Shareware Promotions - http://www.sharewarepromotions.com )
#2. Alastair Rampell - Alex always has a unique perspective and innovative ideas. ( TrialPay - http://www.trialpay.com )
#3. Phil Schnyder - Phil is a riot, I go to his sessions just for their entertainment value, though they usually have some good info.
I'd enjoy hearing Joel and Malcolm Gladwell go toe-to-toe over outlier data and cherry-picking your personal experience to make a point! It would sell a lot of $10 tubs of hotel popcorn.
But seriously, how about one of the senior Harmonix developers? Given the sheer economic size of the video game industry, it'd be intriguing to hear how they became an overnight success after only ten years plugging away at music-themed development.
How about a guy who's taken the big risks you always talk about despite intense criticism from both the mortar-and-brick and web 2.0 crowds, and always finds innovative ways of generating revenue? I'm talking (once again) about Jeff Bezos of Amazon.
Robert Hoekman, the author of Designing the Obvious.
There are only two books that I can give to anyone in my company and know that they'll come back more focused on being productive in the real world.
The first one is (of course) "Don't Make Me Think", so it was great that Steve Krug was at the last conference and even greater that his video is available.
The second is "Designing the Obvious" which instantly transformed my business partner (among others) from a feature-wishlist-generating-machine to a hack-and-slash-feature-conservative. I'd give pithy quotes from the book but I literally can't find any of my 3 copies because my employees keep stealing it.
It's no coincidence that both books are short, funny and have loads of groovy pics and cartoons, so I don't think it would be a coincidence if Robert is as entertaining and enlightening a speaker as Steve (disclaimer: I've never met, seen or even emailed the guy, so this is speculation - I just know I'd be more likely to show up at BOS 2009 if he were there).
Marty Cagan, author of "Inspired: How to create products your customers love" is a very engaging speaker with great ideas. I saw him speak recently at an SVPMA event, and came away with a number of insights and takeaways around product management.