I am in the beginning stages of two campaigns at the moment, both being run in Heroes By Trade. Normally I love to rant about how I am better than everybody else and my games are superior but this time I really need to steal a play from somebody else's book. In The Hat started up our group by having us sketch out characters in very broad terms and then collaboratively building stories that would get us together. We talked about how we might get ourselves to a particular place where the action was slated to begin and figured out ways in which everyone could meet and have some reasonable expectation of cooperation. I had plenty of ideas and a bit of a history already built but everyone else was pretty much starting from scratch. This worked quite well; we did have to kludge a little to get everybody together but we are starting the real action soon in a situation where we have a bit of time together under our belts and at least some reason to be grouped up.
Things aren't going as well as that in the campaign I started. I gave people a starting location (a whaling village) and a bunch of random details about the place that were intended to let them build a character with some attachment to it. I ended up with one character who was invested in the village and two who were outsiders only recently arrived. This was particularly tricky because when the action started none of the characters knew each other and we had to force it a bit to get them to work together. It wasn't bad exactly but it wasn't as smooth as I would like. I also kind of forgot that new players are often confused about what to do and initially I gave them a lot of options when I should have put them in a situation with clear objectives, perhaps as part of a military unit or somesuch... just like In The Hat has arranged in his game.
No matter how experienced I am as a GM and no matter how good the system is I should never forget that spending time building a good start to a game is key. It is all well and good to let the players have total freedom designing their characters but care must be paid to ensure a cohesive start so they can build a base of trust and familiarity before their crazy choices and backgrounds cause all kinds of friction. I want that friction and the interesting events it creates but I really need to get them sorted out and pointed in the right direction first.