Earlier this week at the Sympatico/MSN Digital Ad summit, I talked with Chris Dobson, who heads up MSN's international sales and marketing efforts. Maybe the most interesting part of the conversation was Dobson's willingness to frankly discuss Microsoft's strategic approach to the advertising market and the key trends within the online marketing world. This was a far cry from the typical read-off-the script "interviews" where senior executives talk but they don't say anything. It was refreshing to get perspective and context rather than a canned sales pitch. I figured Dobson had something to say when the first thing he said was "Microsoft has woken up to the fact online will not be a subscription world but an ad world". This led to a discussion about how Windows Live will be a hybrid between ad-supported and fee-based content/services, and the balancing act facing companies with portals (AOL, Yahoo, Microsoft) at a time when user-generated content is becoming more popular. It was also interesting to hear Dobson's belief many ad agencies are still dealing with the Web in isolation rather than putting together coordinated campaigns with print, radio and television. Clearly, Microsoft is serious about the online ad market and trying to appear as advertiser-friendly as possible. At the very least, it was encouraging to run into a Microsoft executive willing to talk about what's happening as opposed to pontificating about the Microsoft Way.