I've been doing this every year for quite a while.
The first trip is a bitch to organize, but every subsequent year gets easier since you use the previous year's template and make changes.
First off, decide what you want. There is no easy or foolproof way to create a plan out of nothing in group setting. Come to the group with your plan and then edit it.
My first year, I came to the group with the following: preferred dates and one alternative, a list of destination criteria (hardcore resort, remote resort, party town, heli-ski options, etc.), a list of accommodation requirements (hotel rooms, private house, no shared beds, private hot tub, fully equipped kitchen, slope side, etc.)
Ditch the people who hem and haw or who want to change everything. This is probably the most important part. If they don't share your vision of what the trip should be (or at least reasonably close) then they're not going to enjoy it and neither will you. Do them and yourself a favor and cut them from the list.
My first trip, I started out with 16 friends who were "interested". 4 of us ended up going and we picked up one extra acquaintance who brought her Dad (super cool guy and a really good skier). Great Time! The next year, word got out about how good the trip was, and I started getting questions/requests from other people in August! 10 went the next year and it was even better. Now it is 9-10 people every year and the next year's trip is generally organized while enjoying the spring slush
Last edited by Bones; 09-09-2013 at 10:54 PM.