Dude(ette), "what do you do?" is literally the most commonly asked question in Toronto. Hung out last night with a few people and this one girl from California, and the first thing people asked her was "oh, what do you do?". I mentioned how that's "so Toronto" and she's like "yeah! Everyone here cares so much about that!" (paraphrasing). We are so career-focused in Toronto. No one asks "what do you do for fun" or "what kind of music do you like" as an opener.
That being said, in terms of the Mayor job, it does require political experience and skill ... if RoFo can be Cllr for 10 years or whatever, it's clearly not a very high bar, but you WOULD expect your Mayor to at least have SOME experience managing large operations, whether as a politician or in industry...
edit: As for who on council would be good for mayor... Adam Vaughan, in my opinion. I mostly dislike the guy, but I feel I could trust him to make reasonable decisions based on facts and expert advice (well, except on the whole airport thing). He's also a loudmouth and a jerk which would be incredibly amusing to see. I mean, not just from an entertainment point of view, but politicians are so shy usually of saying how they truly feel. A more practical example would be Krystin Wong-Tam...